ZEALOUS NOVICE BOTTOM STARTS NEW LIFE AT THE BARBER SHOP

I first began realizing that Linda was a hot submissive when she began to point out every bald person we ever saw on television. I had been friends with her for about a year before we really got to know one another. Eventually we became lovers and moved into the same house.

We had been having normal girl girl sex for a few months, but nothing out of the ordinary. Then Linda began showing great interest in key items, like police handcuffs, leather biker jackets, thigh high boots. I began to see wild new possibilities for our relationship.

She was always dressing in leather minis, wearing only stockings and hardly ever a bra or panties. She was fascinated by the idea of shaving. Linda had often paused at beauty shop windows and asked me if she’d look nice with her long brown hair cut short. When I’d say sure, she’d say, “I mean really short.”

One time after a night on the town, Linda and I hit the sack. I was especially hot that night and needed more than our usual dildo and tongue session. I told Linda that she did not seem happy and asked her if there was something missing in our life. She responded quickly that she missed not having someone to take care of her totally.

That was my opportunity, and I told Linda that our relationship was going to change. She needed someone to take care of her needs, discipline her and reward her. She breathlessly agreed. I asked her if she thought that she was capable of being my house slave. She whispered yes, then dropped to the foot of the bed at my feet. I said that I was glad she agreed. Then I used my old suitcase straps to secure her on the floor and told her in no uncertain terms that we would begin a new phase in our relationship in the morning.

When I awoke, Linda had a hot look in her eyes. I told her the weekends would be mine, with her as my sexual slave. She would do exactly as I said, because I knew what was best.

To start out her new life, Linda brought out all of her clothes to me for an inspection. She said she didn’t want to wear anything I didn’t really like her in. I approved of her leather minis and halter tops, but all the pants and skirts longer than mid thigh had to go. The bras, panties and socks: ditto.

Next I took Linda into the bathroom to look over that gorgeous body. I immediately took away her jewelry and makeup, luxury items not appropriate for a slave. Linda had these long painted fingernails that certainly would hinder her new chores around the house. She clipped her fingernails and toenails right in front of me. Linda’s pubic bush was a pretty shade of brown, but slave usually don’t sport cunt hair so out came the razor. Linda was getting very hot, but we were not finished.

Linda and I went to the mall to complete her transformation into my slave. She had never been this hot. Linda was wearing a black leather mini, a tube top and boots. The first stop was the pet shop, where I bought her a nice set of collars. Thank goodness for credit cards, because the next stop was the shoe store. The clerk got a hard on looking up Linda’s mini as she tried on her spiked heels. Naturally, I bought her the black pair that were so high, Linda could barely walk without stumbling. I was sure she could adjust.

Shopping for clothes was fun indeed. The staple of Linda’s wardrobe was leather miniskirts in black and red. One skirt was so short that when she bent down slightly, her shaved cunt was exposed. I paired her skirts with cut off tops and sheer blouses to create a few outfits for a deserving slave. The one special outfit we bought was a French maid’s uniform for Linda to wear when tending to her duties. The dress was cut short, with a plunging neckline, and had a matching cap and apron.

The day had been quite a success, but I knew the thing she was really waiting for was her haircut. The barbershop in the mall was quite busy, and boy, did Linda stick out there. I spoke to the barber myself, while Linda was permitted to give only a yes or no answer. I told this male barber of about fifty to cut Linda’s shoulder length brown hair to her chin. Linda nodded yes.

After a few minutes of chopping inches and inches off, the barber asked if it was okay. I approached Linda, looking into her eyes, and said to cut it shorter, up to her ears. With that Linda squirmed in her chair, apparently near orgasm, nodding to go ahead all the while. This took a little longer, as the hair was coming off in clumps. There was a huge pile of brown locks on the floor.

I looked at Linda’s new short man’s haircut and said that it was just not right somehow. Linda opened her eyes wide in excitement and anticipation. I asked her if she would like to go shorter. She nodded yes. The barber asked, “How short is shorter?” I said to give her a crew cut! The barber was obviously upset at having to spend so much time on this one haircut, so he hurriedly drew out his clippers and clicked them once. “Okay, ladies, here goes!” he said.

The sudden loud buzzing startled Linda, but the barber was giving her no time to think this over. He ran the electric clippers from her forehead to her neck, taking off piles of hair and leaving nothing but stubble. The other customers were openly gawking now, but we were both in a wild state of sexual arousal.

The scene was not over yet, though. Linda was dying to go all the way. This was her dream, her fantasy. I ran my hand over Linda’s prickly scalp and asked her if she would like to finish the job, as having come this far, we might as well go all the way. Sitting in the barber’s chair, squirming on her wet cunt, Linda finally spoke something other than yes. She said, “Shave it bald!”

The barber said, “Well, you dames beat all!” He brought out the shaving cream and lathered Linda’s head. With a straight razor he had sharpened on his razor strop, he began to shave away the stubble from Linda’s head. In a few minutes she was bald, smooth and hairless, and gripping the armrests tightly as a powerful orgasm rocked her from head to toe.

Linda’s transformation was finished. Her fantasy had become reality. During the weekdays, Linda and I lead very average lives however, where she works the have had to accustom themselves to Linda’s proudly bald head, which is shaved nightly. On the weekends Linda becomes my slave and is at my sexual disposal.

Ms. C.W., Missouri

BLOWJOB FANATIC SURPRISES FELLATIO LOVING FELLOW WITH UNEXPECTED ORAL DELIGHTS

“What I want to know is what happened to all the girls who give head on first dates,” Vince exclaimed, his beer sloshing slightly as he pounded his glass on the table. “Do girls even do that anymore?”

I stared blankly for a minute, taken aback by the turn our conversation had taken. We’d been discussing college basketball we’d gone to the same school, but a few years apart and our mutual friend Serena. Now all of a sudden he’d thrown sex into the mix. Sure, we’d touched on bad date stories he’d met Serena on a blind date, after all but we were nowhere near familiar enough to be dishing on our sex lives. Then again, I thought, he’s pretty cute. A little sex talk couldn’t hurt.

“I don’t know,” I said. “I’ve never been on a date with a girl, so I couldn’t tell you what they do.” He looked at me, obviously surprised by my response. He seemed amused, almost impressed, by my answer, so I went on. “I can tell you that I still give head on the first date.”

The look on his face was priceless. It was clear he’d been going for shock value, and by taking him seriously, I’d completely blown his mind. I laughed. It was obvious he wanted to say something, but Serena returned to the table and he didn’t have the chance.

The three of us had a few more drinks and chatted awhile, and when we were ready to go, Vince offered to drive us home. He lived closer to Serena, but he still dropped her off first, leaving us alone in the car.

“Smooth move,” I joked as he pulled away from Serena’s apartment building. “Do you think something’s going to happen now that we’re alone?” I managed to keep a straight face as I said that, and Vince’s look of shock proved that he had been but that he didn’t expect me to be the first to bring it up.

I let him sweat for a minute, not saying a word as he stuttered through what sounded like an apology. Then, as he quieted down and turned his attention to the road again, I reached over and popped the button on his jeans, pulled down the zipper and eased his cock out of his pants. Vince practically jumped in his seat when I grabbed his dick, but he managed to control himself and continued driving down the road as if nothing was happening. It became more difficult for him to keep his eyes on the road as I started to stroke him, but he managed for a few more miles. His cock was half hard by the time I suggested he pull over, and his dick was as solid as a rock within minutes of stopping the car on a little traveled side street.

Reaching down further, I found the lever that controlled the seat’s position and pressed down. Vince figured out what I was doing and quickly pushed his feet against the floor, easing the driver’s seat back another foot. There was now plenty of room between Vince and the steering wheel. With one hand grasping the base of his cock, I leaned over him and lowered my head to the crown of his dick. It was slick with pre come, and my first lick brought me a taste of his salty come. I didn’t stop to savor it, though I had a point to make, and I needed to get to work.

Lowering my head further, I took a couple of inches of his shaft into my mouth, then pulled up, leaving his cock wet with my spit. When my head next bobbed down on his cock, I took more of it into my mouth before pulling off again. I did that over and over, teasing him with the possibility of what was to come with the next stroke, and he moaned, his fingers wending in my hair, trying to hold me in place or push me down further. But I remained in control, and when I wanted to pull back, I did, no matter how hard he tried to fight it.

Finally I gave him what he wanted, deep throating his shaft until the head of his cock nudged the back of my throat, and I had to swallow a few times to be able to hold him there without gagging. From the way he pulled my hair and groaned loudly so loudly that his entire body vibrated I knew he liked it. The truth is, I did, too, and this simple act was making me unbelievably wet. I’ve always liked sucking cock, especially when it’s the cock of a new guy, and deep throating is my specialty. Vince’s cock was average in size, perfect for my favorite hobby, but I’d managed to swallow a ten inch dick once, so I knew Vince would appreciate my talents.

When I could no longer hold him in my throat, I eased my head back and started bobbing up and down on his shaft again. I was getting really excited, and I felt my cunt throbbing as I continued to service Vince’s shaft. Reaching back, I shoved my free hand in my pants and started playing with my wet pussy, trying to get myself off as I did the same for Vince.

I moaned around Vince’s cock as I fingered my cunt, and that brought him closer to the edge. Pre come was pouring into my mouth as I sucked him, and I knew I would be swallowing his seed in a matter of minutes, maybe only seconds. That only made me work harder, and I powered up and down on his dick, pulling his cock completely out of my mouth on every fifth stroke to lick him all over. With the hand that had been gripping his shaft, I started to play with his balls, massaging them and squeezing them lightly, nudging him toward his climax. I was nearing my own orgasm by then, too, my now slick fingers working furiously to make me explode.

For the final strokes, I lightly grazed Vince’s dick with my teeth, and that did it for him. He came on the next stroke, and I had to swallow rapidly to keep up with the stream of come he was feeding me. By the time the third shot hit my tongue, I was coming, too, and I felt my own juices flood my panty crotch, completely soaking the cotton.

I finished sucking Vince, milking his balls until he’d given me every drop of semen that he possibly could, and then I pulled back, wiped my mouth on my sleeve and zipped him up again.

Vince didn’t move for a few minutes, he just lay back in his seat, with his head thrown back as he tried to catch his breath. When he finally sat up straight and looked over at me, I simply smiled and continued directing him to my house, as if nothing out of the ordinary had occurred between the two of us.

When he pulled up in front of my place, I hopped out of the car and walked around to the driver’s side window. I tapped on the glass, and when he rolled down the window, I leaned in and said, “You should see what I do on the second date,” then hurried toward my front door.

Serena called the very next day, wondering what I’d done to make Vince text her for my number at three in the morning.

“Nothing special,” I said. “I just treated him like I would any first date.” But I wasn’t surprised when he called the next day for an encore.

Ms. Tegan R., Atlanta, Georgia

GALLERY’S BONDAGE DISPLAY INCITES A GIRL/GIRL COUPLE TO BREAK OUT THE CUFFS

My girlfriend, Susan, is always roping me into going to “cultural events,” as she calls them. I tend to think of them as snoozefests, and I’ve actually fallen asleep at everything from the opera to foreign films. I encourage her to go with friends who are interested in those things, but sometimes they’re busy or she wants my company and she’s so sexy, I can’t deny her.

She and I met when mutual friends fixed us up, and I was so smitten with her bouncy black ringlets of hair, her freckles, cute laugh and beautiful body that for the first few months I was happy to go along with anything she wanted. I would put up with the artsy nonsense while I’d fantasize about what naughty fun we’d get into later.

But recently she surprised me when she waved a newspaper in front of my face while I was watching my favorite game show, Jeopardy! “What?” I asked, ready to roll my eyes at the latest dance performance or obscure abstract art showing.

“Just look,” she said, with a touch of defiance in her voice. I glanced down and felt a tingle of arousal spark between my legs. There on the page was a photo of a woman in profile, her arms bound behind her body with lengths of white rope that looked beautiful against her tanned skin.

She then smirked at me smugly because I’d actually shut off the TV to read about the exhibit, which promised explicit photography by various local artists. You had to be over eighteen to enter the gallery. The words teased me, as did the images that popped into my head. Susan and I have a great sex life but had never done anything kinky like bondage, save for one of us holding the other down by her wrists. Once I’d wrapped a scarf around Susan’s eyes when I was leading her into the bedroom to show her a surprise, but we’d never used the scarf in a sexual fashion. Now, seeing how beautiful the model in the photo looked, I wanted to go both to the exhibit and bind my girl . . . or maybe even let her do it to me.

I grabbed Susan and pulled her close for a kiss and then asked, “Baby, what do you think is going to be so exciting about this?”

“Well . . . all those photos of hot women. And rope. Sometimes I think about you tying me up,” she confessed quietly. Susan’s not usually shy, but in the past when we’ve talked about experimenting sexually, I know she’s wanted to make sure I’m on board before sharing her fantasies.

“I think I could manage to tie you up. Maybe tie you to our bed and take dirty pictures of you.” She bit her lip, and I couldn’t tell if she liked that idea or not, but then I noticed her nipples becoming erect beneath her shirt. I reached down and stroked her pussy through her panties, which were soaked. “Maybe I’d play with you just like this, only you couldn’t grab me, couldn’t reach for me. You’d just have to be patient. Maybe I’d drip hot wax on your chest, over your nipples, down your belly . . . ”

We spent the next two hours sharing our fantasies about what we might do in all sorts of delicious bondage scenarios, whispering and stroking each other until we’d each come three times. We lay in bed, sated, and she kissed me deeply, then hopped up and began rummaging through her closet for something sexy to wear to the gallery. I lazily watched her and urged her to wear a sexy black dress with no panties and my favorite black and white heels.

The images at the gallery were even more risqu than I had imagined they’d be. It wasn’t just that the women were in bondage, but also that the looks on their faces were exquisite. To put it simply, they appeared to be in the throes of orgasm. There were women with their heads thrown back and others staring at the camera, all with their lips red and glossy. Even when what was going on in the photos looked intense clothespins on nipples, and other places, and rope bondage that secured limbs in unnatural positions the women looked aroused.

The photographer and some of the models were actually at the gallery and spoke to the crowd. I held Susan’s hand as we listened to the ladies discuss the shoot and talk about what it was like to get bound with rope, what they enjoy about being restrained, and the experience of posing and being on display. Susan squeezed my hand at certain points, letting me know she was both intrigued and aroused, and I couldn’t help but picture her trussed up just like the women in the photos.

By the time we were done seeing all the art, we were both so turned on that we were practically climbing the walls. We stopped at a sex shop on the way home, which we hadn’t done in a long time, and though Susan blushed, I insisted on asking the saleswoman to explain the various bondage devices they offered. She even let me bind Susan’s wrists together with some bondage tape, which made me unbearably wet and thrilled my girlfriend, too. I’m sure the clerk heard the little moan of excitement that escaped her lips. We wound up spending more than two hundred dollars on everything from padded cuffs to a blindfold with fake fur on the inside, as well as nipple clamps, a feather tickler and some pink bondage tape.

When we got home, though, something had changed and my girl had decided that she wanted me to be the first to be tied up! I wouldn’t say I’m particularly submissive, but I love indulging her, and I was also curious about what the girls in the photos had felt like. “Now take off all your clothes,” Susan said, a bossy tone in her voice.

I started to obey, but she insisted I hurry. “Faster or I’ll make you pay.” Part of me wanted to laugh, because Susan is so cute that I couldn’t really picture her as a domme, but when she glared at me, I knew she was serious. I stripped off the rest of my clothes and surrendered to her. She immediately fastened the cuffs around my wrists and then traced the tickler along each of my armpits. I found myself slowly submitting to her vision of me as her captive, and I found that as type A as I usually am, it felt good to give in.

Susan pinched one of my nipples, and I gasped. “Do you want me to put the clamps on you?”

It was a trick question, because I did and I didn’t. The longer I took to answer, the more she played with my nipples until I finally relented. I had never had someone use clamps on me. “We can take them off if it’s too much, but I don’t think it will be,” she said as she stroked my wet cunt.

I held my breath as she fastened the clamps around my engorged nipples. I bit my lip and tugged at my bonds, but I couldn’t escape, and in truth, didn’t really want to. Susan leaned down and kissed each breast, then let her tongue trace the small bits of nipple that weren’t inside the clamp. “Yes,” I couldn’t help but moan. Everything about what we were doing felt so good, including giving up my role as the more dominant woman in our relationship.

Susan seemed to grow into her power and was soon tonguing and teasing my pussy simultaneously. Whereas normally she’s eager to lick me to orgasm, this time she licked along my slit leisurely, shoved her tongue into my hole, suckled on my clit, and then sat up and gave me a grin as she showed me how wet she was! There was only so much of this erotic torment I could take before I was begging her to let me come.

“I like hearing you beg,” she said as she slid three fingers inside me. “Keep going,” she instructed, and I promised her all sorts of things visits to museums, wine tastings anything to get her to give me what I wanted. Finally the tremors shook my body, and it felt even better because I couldn’t move my arms or flail around like I normally would.

I was sweaty, flushed and hot all over when she finally unfastened my bonds. She kissed me passionately, and I moved her so she was sitting on my face, her sweet pussy filling my mouth. “In the morning, you better be ready. I’m going to tie you up and use your favorite vibrator on you,” I told her.

“I can’t wait,” she said, and we curled up together, both excited about the possibilities awaiting us.

Ms. Eliza C., Portland, Oregon

LOVER OF SMALL BREASTS FINDS JUST THE RIGHT HANDFUL AT A STRIP CLUB

I don’t go to strip clubs as often as some of my pals, because although my favorite feature on a woman is her breasts, I tend to prefer they be on the smaller side. “Less is more” is my motto when it comes to tits, yet most women seem to think the opposite, especially strippers. They try to entice me with their oversized boobs, and while I try to be polite, bulging jugs just don’t do it for me.

But when my best friend, Frankie, begged me to go to our local strip club with him, I said yes. I knew he was heartbroken over splitting up with his girlfriend of four years. I figured it couldn’t hurt to check out some naked girls, although I’d assumed there wouldn’t be any ladies there that I’d find attractive.

While some guys like to lie down and have women’s boobs dangling above their faces, I like being able to hold an entire breast in my hand. I also find that girls with smaller boobs tend to be shorter and more compact, and I can easily lift them up and toss them on the bed. Despite all this, Frankie and I headed over to the club, and I was happy to see my pal smiling and joking around in a way he hadn’t done in weeks.

Frankie immediately bought a lap dance from a busty blonde while I looked on. I wasn’t unhappy, but I had a feeling that it would be my friend and not me who would be getting lucky that night. I don’t mind watching pretty girls dance, but I didn’t expect to be shelling out extra cash to any of these buxom ladies.

As Frankie enjoyed his dance, I casually surveyed the room and found that most of the dancers had breasts in one of two sizes: big and bigger. They were either pleasingly (to most) plump or enormous. All around me were jiggling boobs that seemed to be making many men very happy. And then I saw her. Raven had shiny jet black hair that fell beautifully around her shoulders and landed right above a perfect pair of A cup breasts that were topped by pointy, ruby red nipples.

Raven’s lips were covered in a shiny pink gloss, and she wore a pair of black boyshorts that clung to her pussy, along with tall black boots. I was smitten. Meanwhile, Frankie didn’t even notice, because he was about to get a dance from a girl who was Raven’s complete opposite, a leggy, tall blonde with boobs that looked like they might hurt if they hit you on the head. At least, that’s what she seemed like to me, but Frankie was in stripper heaven.

I slipped away so I could get closer to the stage and the petite goddess who was dancing on it. Thankfully, most of the men there shared my friend’s taste and were scanning the room for the biggest tits to nuzzle up against. I started handing dollar after dollar to Raven, hoping I would get the chance to feel those sweet little breasts up against my face. She kept giving me these sexy smiles and shaking her ass in my face. Her bottom was also small but perfectly proportioned. When her song was done, she leaned toward me and ran her red fingernail along my cheek, making me shiver.

“Hey, big spender,” she said, making me laugh, “want a private dance?”

“Yes, I do,” I said. She asked me my name and what I did, making small talk while she slipped her hand into mine. At that point, I wasn’t really sure what was going to happen, but I figured Raven was in charge. She took me into a back room, drew a curtain around us and held her breasts up, as if she were offering them to me. I liked that, so I paid her, and she began dancing for me.

I knew Raven could tell that my cock was rock hard she’d have to have been oblivious not to notice. I figured I’d get as many dances as I could and then go home and jerk off. I sat there, mesmerized by her beautiful body especially those breasts. She tossed her hair back and thrust her tiny tits forward so they were right in my face. “You can touch my breasts . . . if you want,” she said, sounding almost disappointed that I hadn’t tried to fondle her.

“Oh,” I said, startled. “I didn’t think that was allowed.”

“With some girls it’s not, but it’s fine with me,” she said. “I like a man who can appreciate what I’ve got. Most guys only want to get dances from the girls who have boobs the size of my head.” I laughed at her remark, glad to know I’d found a kindred spirit.

“I think your breasts are perfect,” I told her, and I wasn’t lying. Up close, her tits were even more stunning, rounded just enough, with what looked like very sensitive nipples. My appreciative eyes weren’t enough for her because Raven then took my hand and placed it on her boob.

“I want you to touch me,” she said, then shut her eyes as she straddled my hips and gyrated against me. She was still wearing her boyshorts, but the heat from between her legs was undeniable. I cradled her tits in my hands, then began running the pads of my thumbs over her nubs. She murmured, “Harder,” and leaned forward so that her face was resting on my shoulder.

I still wasn’t sure what was and what wasn’t okay according to the club’s management, but I couldn’t deny such a hot chick. I squeezed her breasts together, imagining my cock gliding in the space between them. When she grabbed my head and brought it to one of her nipples, I sucked the nub of flesh between my teeth, soon forgetting that we weren’t in a totally private setting. Having her beautiful breast in my mouth made my cock so hard I thought I might come on the spot.

“I want you, Charlie,” she said when I released her nipple and moved on to the other one. I spent the entire dance sucking frantically on her tits while she shook her body around, occasionally pulling away from me to draw out the intensity of having my lips latched on to her. Finally, we had to stop so she could go dance onstage again, so I tipped her handsomely, and then she slipped me her number. “Call me at two and let’s finish what we started.”

I returned to Frankie, who was sitting at a table, nursing a beer. “Dude, where were you?” he demanded.

“Getting a lap dance.”

“For thirty minutes? She’s flat chested!” He made it sound like I’d been cheated.

“She’s got gorgeous tits, they’re just not the size of cantaloupes,” I said. “Forget it you wouldn’t understand, but she and I have a date later tonight.”

“No way!” He looked shocked, and a little jealous.

Frankie and I hung out for the rest of the night, watching girls until he wanted to leave. I said good bye, and then went to a diner for a burger before calling Raven. “You can call me Jill,” she said when she answered her phone. “Can you pick me up?”

“Sure,” I said. I brought her a hot chocolate from the diner, and she seemed delighted with her treat. She drank it slowly, and then let me lick the sweetness off her lips. We didn’t even make it out of the strip club parking lot! She insisted we climb in the backseat so I could fuck her.

“I did really well tonight because I was so horny from our makeout session,” she said breathlessly. “I made more money than I ever have, but I don’t care about that. I just need your cock!”

I was more than happy to oblige, pounding into her hard and then sucking on her nipples once again. She came twice while I fucked her, and then I couldn’t take any more of suckling her tiny tits. I pulled out and jerked my dick until I came all over her boobs. She scooped up my cream and fed it to herself, and watching her do that got me hard again. Jill sucked my rejuvenated dick, and I fondled her tits until I exploded again, and then we finally retired to my place. I woke up with her pressing her tits against my face, and we’ve continued to see each other as often as we can. Every time I tell Frankie I can’t hang out because Jill and I have a hot fuck session planned, he cracks jokes about her small boobs, but I know he wishes he had a hot stripper to screw. I’m a lucky man, and I know it.

Mr. Charlie O., Austin, Texas

WHEN THIS STOUT SUB FAILS TO PLEASE HIS MISTRESS, SHE PUTS HIM THROUGH HIS PACES AND THEN SOME!

Mistress Mischa’s crop smacked her palm as she counted off my sit ups. Each thwack coincided with my upward movements, and when I didn’t move in sync with her slaps, she turned the crop on me. For most of the workout I’d kept up with her pace, but as we neared the end of the session, I couldn’t do it anymore. My muscles were exhausted. I was moving slower and slower, and my final sit up didn’t meet my mistress’s expectations.

I saw it coming, or at least I should have, but when her crop’s keeper landed firmly in the center of my chest, I felt like the wind had been knocked out of me. My mistress was disappointed in me, and I couldn’t imagine what the consequences would be.

“Why can’t you do a simple sit up?” she demanded. “You said you do your workouts at home. Have you been lying to me, slave?”

“No, Mistress,” I cried, “I would never lie to you.” But I had lied to her. I hadn’t done my workouts that week, being too busy with work to bother with lunges and squats, treadmills and step machines. I didn’t expect her to notice, though I thought I’d still be able to get through the rigorous training session. I was wrong.

Without giving me any warning, Mistress Mischa was pushing me back down onto the floor, her red soled pump planted firmly on my chest. “If you’d been following my instructions, you’d be able to do a basic sit up,” she insisted. “You can’t. Therefore, you will be punished.”

Mistress hadn’t had reason to punish me in weeks, and I almost couldn’t remember what her punishments were like. Was she going to flog me? Suspend me? A tiny part of me hoped that the punishment would simply be extra sit ups, but I knew that was unlikely and, in truth, I preferred my mistress’s harsher punishments, anyway. I tried to keep quiet as Mistress Mischa’s sole pushed harder on my chest, all of her weight on the front of her foot so her heel wouldn’t hurt me. She inched her foot higher on my chest until the toe of her shoe was pulling my chin down, and then she demanded that I lick the patent leather. As I worshiped her shoe, being careful not to slobber too much, she told me what my punishment would be and I couldn’t silence the moan that rose in my throat at the thought of proper discipline.

I was informed that I would be doing the entire week’s worth of sit ups, and that Mistress Mischa would sit on my cock as I did them. But I wasn’t allowed to fuck her I had to keep my mouth shut and my cock still or I would have to do double the work to get back in her good graces.

With that, Mistress took her heel from my chest, planted her feet firmly on either side of my waist and lowered herself, her latex covered pussy hovering over my dick for a second before she settled into place. She was facing me, and each time she wanted me to sit up or lay back, she would reach back and swat my thigh with her crop. The first few weren’t so bad, aside from the general annoyance of doing the sit ups. But after a half dozen repetitions, not only did my abs hurt like hell, but I could feel my cock stirring and worried that Mistress might feel it, too. Between the constant smacking of her crop and the feel of the latex against my dick, which was warm from her hot pussy, it was nearly impossible to control myself. I pushed myself through sit up after sit up, praying that Mistress Mischa wouldn’t notice how aroused I was.

Of course, my mistress is a professional and knew right away that her punishment was turning me on more than was appropriate. With one final swat, she rose from my lap and demanded that I get on my hands and knees. “If you can’t handle doing a simple sit up for your mistress,” she scolded, “perhaps doing push ups will help you learn your lesson.” I paled at the thought even when I did my at home workouts, I couldn’t do more than a handful of push ups before dropping. But Mistress insisted, and I had no choice. Steeling myself for an even tougher workout, I got into position.

This time my mistress sat astride my back and smacked my ass each time she wanted me to move. If I’d thought the sit ups were bad, push ups were ten times worse, especially with my mistress petite though she may be sitting atop me while I tried to push my considerable weight off the floor over and over again. I strained against the weight, though, and forced myself to think only of the feeling of success that would come if I managed to please my mistress. Surely she would be impressed if I could do a series of push ups without complaining and without getting aroused and without collapsing.

After every third or fourth push up, Mistress would reach under me and tap my cock with her crop, checking my state of arousal and urging me on. I did a dozen push ups without getting too turned on, then fifteen, but by the time Mistress Mischa’s count reached twenty, my dick was growing hard. I tried to hide it, to think of anything except the gorgeous crop wielding woman on my back, but every thought went back to my mistress, and she’s so stunning that I couldn’t help getting excited.

By the twenty fifth push up, I could no longer hide my hard on, and Mistress had found me out. “What’s this?” she demanded. “Didn’t I tell you to control yourself?”

“Yes, Mistress,” I said.

“Then what’s your excuse?” she hollered.

“I was thinking about you, Mistress Mischa,” I whimpered. “I tried not to, but I couldn’t help myself.”

Standing, Mistress Mischa walked around me, smacked me one more time on my ass, allowing me to sink down on my knees, and then pushed me over onto my back with her foot. She stepped over me, her glistening latex panties positioned over my face, and looked down. “You did twenty five push ups, slave,” she stated. “That’s a record for you. In fact, not only did you complete your punishment I think you’ve earned yourself a small reward.”

“Thank you, Mistress,” I cried. “You’re too kind.”

“You will do your workouts at home like you’re supposed to from now on, won’t you?” she questioned, and I nodded. “And when we meet next week you’ll be able to do all of your sit ups and extra push ups, right?” Again I nodded and assured her that I would be in tip top shape during our next session. “All right, then,” she said. “You can have a reward.”

With that, she pushed the latex crotch aside and planted herself on my face. She said I could eat her to orgasm, and that I was allowed to jerk off and come after she was finished!

I dove greedily into her cunt, savoring the smell, her natural scent enhanced by being trapped in the latex for so long. My tongue darted out and swept up the sweat and juice that had gathered along her cunt lips. She tasted bitter, and I loved it! I lapped up every drop of dew that clung to her outer lips before letting my tongue delve deeper into her slit. I moaned as I felt her pussy envelop my tongue, and I tried to force out every flavorful ounce of juice that she had to offer. Then I added her clit to the mix, nuzzling it and sucking it and biting it in between tastes of her pussy. By the time my taste for cunt had been satisfied, Mistress was coming, and I got one more delicious drink of her juices before she was finished.

Then it was my turn, and I worked vigorously, pumping my cock so furiously that it took less than a dozen strokes to get me off. I shot my come all over my stomach as I came, my mistress watching the whole time. When I was finished, she tossed me a towel and ordered me to clean up. She told me to be back the same day and time the following week and to make sure I did my workouts while we were apart.

You can bet I’ve spent a lot of time doing sit ups and push ups this week, in preparation for my next meeting with Mistress Mischa. I’m hoping that if I impress her enough, she’ll finally let me fuck her! I’ll let you know what happens.

Mr. David S., Denver, Colorado

IT’S A TOWERING TURN ON WHEN A HUNG HUNK BANGS HIS HOT WIFE

Ever since we married, I’ve had a fantasy about watching my petite wife get it on with a big guy. I’m only five foot six, and while I’m taller than Marla, it’s not by much. My cock is okay, but it’s fairly average sized, and I knew from talking to her that most of her previous lovers had been well endowed, husky types. I felt bad about depriving her of the joy of a larger cock, but I also selfishly had the desire to watch her screw another man. Yes, I wanted to see a big dicked guy fuck her, even get a little rough with her.

I’d mentioned my fantasy to Marla once or twice, and she seemed intrigued, but I didn’t think she understood that it was my go to fantasy for masturbation something I fervently hoped would happen one day. I didn’t want to pressure her, and I figured we’d deal with it if a guy ever caught her eye and we had a convenient opportunity to take things further.

Well, the opportunity arose one day when we stumbled upon a pickup basketball game in the park. All of the guys playing were a good deal taller and broader than me. When Marla saw the men, her eyes lit up and theirs did, too, when they got a glimpse of her. My wife is short but curvy, with blonde, wavy hair and large breasts that were barely hidden by her snug white tank top. She was also wearing the shortest shorts she could get away with wearing in public. She looked good, and she knew it.

I stood behind her with my arms casually draped around her waist, resting my head on her shoulder as we watched the game. I was trying to look relaxed and not possessive, because I didn’t want to scare away anyone who might be in to her. As it happened, most of the guys were put off by me being so close, but one player, Jake, was bold enough to wink at her while he was playing, and Marla made sure he knew that she was watching him with sensual interest. He was soon well aware of the depth of her appreciation of him.

During a break in the action, I wandered off to get a soda, occasionally sneaking glances at my unattended wife. I noticed that Jake had approached her and she was chatting with him, flirting even. At one point, he put his arm around her, and I felt a shiver of excitement run through me. When he returned to the game and I to my wife’s side I saw that her face was flushed. “I told Jake that if his team won, I’d fuck him provided you could watch.”

“Well, that sure is an incentive!” I said, impressed with my wife’s ingenuity. I knew that I would have been playing my heart out if she’d made such a proposition to me.

We both cheered for Jake’s team as he ran extra hard and played with a determination he hadn’t shown earlier. I liked that Marla and I knew the real reason he was working up a sweat. When his team won by thirty points, I squeezed my wife and gave her a lusty kiss. “Congratulations,” I whispered in her ear as my dick swelled in my jeans. “Are we going to take him home with us?”

“Let’s spring for a hotel room!” she said. “I don’t want to wait.”

I was more than willing to indulge her after all, she was about to live out my biggest fantasy. I only hoped that Jake had a cock big enough to satisfy her, but we’d soon find out.

Jake said good bye to his friends and jogged over to us. He shook my hand and then kissed Marla on the cheek. She rose up on her toes to whisper in his ear, no doubt cluing him in to our kinky little plan. Jake smiled broadly and said that sounded great to him, before he stepped away to gather up his stuff.

My wife had told him we were headed to a nearby hotel, and she’d asked about his cock! He’d promised her it was nine inches long and fat. I admired my wife’s spunk, and knowing that she was asking a stranger about his dick was such a turn on for me. I was as eager to watch them as Marla was to be watched. They’d already made a connection. All I had to do was step back and enjoy.

As the three of us headed toward the hotel, I let them walk ahead of me, keeping a few paces back to give them some privacy. They held hands, and Jake reached over and fondled her ass a few times, making my cock jump in my pants.

I could hear their voices, but I wasn’t close enough to hear what they were saying. I liked that my wife was flirting like a single woman would. Sometimes when you’re with someone for a long time, you get too complacent. Seeing her acting so sensually made me remember the moment we’d first met, when I wasn’t sure she’d choose me over another guy she’d been chatting with at the bar. Back then, I was apprehensive, but this time, I was confident that she loved me, so I could enjoy the sight of her with another man.

Once we got to the hotel and settled into our room, we had some wine from the minibar as Jake and Marla flirted some more. When our glasses were empty, Marla suggested to Jake, “Why don’t we take a shower?” Jake didn’t disagree, and she walked up to him and stripped him out of his clothes.

My heart was pounding with excitement as I stayed at a polite distance while the two of them got naked. I followed them into the bathroom, and fortunately, the shower door was made of glass, so I could watch them under the spray and specifically watch Marla’s hands wander all over Jake’s toned body, including his impressive looking cock. It was as big as he’d bragged, and I knew that my wife’s cunt must have been dripping from the sight of it. They soaped each other up and rinsed off under the cascading water, occasionally stopping to make out passionately. When they were totally clean, Jake took control, turning off the water and telling Marla to face the wall and place her hands above her head.

“Stay there. I’ll tell you when you can move,” he said sternly. Hearing him boss my wife around made me hot. Between my throbbing cock and the steamy air in the bathroom, I needed to strip. I did so quietly, so I wouldn’t disturb them, and started stroking my cock. I kept my eyes locked on them as Jake instructed Marla to spread her legs. My wife obeyed, and her lover knelt down and began tonguing her pussy. Of course, I couldn’t see everything from where I was standing, but that was okay. My wife was taking orders from another man and getting her cunt licked by him. That was all I needed to know.

As she squirmed on Jake’s face, he reached up and played with her nipples. It was the sexiest thing I’d ever seen. Jake soon ate my wife to an orgasm that had her moaning. Once she’d caught her breath, they stepped out of the shower. I handed them each a towel, standing there with my cock sticking straight up, but neither of them seemed to mind.

“Hi, baby,” Marla said, giving me a quick kiss before letting Jake lead her into the bed.

“I think you deserve a spanking, Marla, for teasing me during the game. You kept flirting with me and trying to distract me when I should have been focusing on my play. I bet that even if I’d lost, you’d have wanted my cock,” he said. And then he surprised me by turning in my direction. “Don’t you think she needs a spanking, Barry?”

“Yes,” I said in a raspy voice. I was so close to my own climax that I had to slow down my jerking hand. I wanted to hold off my orgasm for as long as possible. The show had just begun!

I sat in a nearby chair, gently stroking my dick as Jake positioned my wife over his lap and reddened her bottom, making her say “thank you” after each smack. When the swats came faster and harder, Marla’s words started to run together, interspersed with little squeals and moans. Jake was doing exactly what I would have done if I were a more dominant type, and I loved every minute of it. My hand was a blur on my dick, moving as fast as Jake’s was as he slapped her perky ass.

After Jake delivered the last firm smack, he shoved his fingers into her pussy. Marla moaned against his leg, her wet hair sticking to her flushed face. At the same time I came, shooting my load onto the carpet. I must’ve made noise when my orgasm hit me because both of them looked at me and chuckled.

“That was so hot,” I said, before joining them on the bed. I settled beside them to watch Jake finger fuck Marla to another orgasm while she was still draped over his lap. After she came, he lay down and pulled her astride him, holding the base of his big dick as she lowered herself onto his shaft. With her on top, I could see his cock as she rode the length of it. He began to guide her with his hands on her hips, raising and lowering her at a slow, deliberate pace and drawing out the pleasure for all three of us. As our excitement increased, so did the pace of their fucking and my stroking. But soon we were all ready for the big finish.

“Do you want my come?” he asked her breathlessly. “Do you want another man’s come in your sweet pussy?”

“Yes!” Marla yelled. “Yes, Jake, I want your come,” she said, and I felt my cock stirring again as I listened to their dirty talk. They moaned and groaned, and though I couldn’t literally see Jake’s hot cream shooting inside Marla, I did watch some of it slide down her supple thighs when he moved her off of him. I even played with it, smearing it along her legs as she lay next to me with a satisfied smile on her pretty face.

Afterward, I took a shower to let them say good bye in private. By the time I came out of the bathroom, Jake was gone, but Marla was raring to go again, getting on her knees to suck my cock before I fucked her sloppy pussy, adding my load to Jake’s.

She didn’t get Jake’s number, but I hope when the mood strikes again, we’ll be able find another well hung man who’ll be eager to fuck my wife.

Mr. Barry S., Tacoma, Washington

VIRGIN HITCHHIKER GETS MORE THAN A RIDE FROM A SEXY OLDER WOMAN

One of my fondest erotic memories and one I recall every time I pass a hitchhiker is from my college days. The night in question happened ten years ago, but I can remember every single moment as though it happened yesterday.

On that fateful evening, my car wouldn’t start and I needed to get home for the holidays. Nobody I knew was free to drive me, so I figured I’d stick out my thumb and see what happened.

Little did I know that not only was I going to get a ride, I was about to lose my virginity to a hot older lady! Yes, I was a virgin at age nineteen, but not because I wasn’t attractive. I’m six feet tall, and back then I was pretty lean and muscular, had a small beard and shaggy brown hair. Girls would flirt with me, but then they expected me to make the next move and I was too hesitant and unsure of myself to act on their interest. Sure, I fantasized about sex a lot. In my head, I was having all kinds of wild sex with beautiful women, but in real life, I had only gone as far as a few passionate makeout sessions.

So when a black Mercedes pulled over and the window rolled down to reveal a beautiful woman, my heart caught in my throat. I guessed that she was at least twenty years my senior, and she had bright red hair, reminding me of Julianne Moore. I managed to stutter where I was going, which made her smile. “Well, young man, it’s your lucky day. You’ve got yourself a ride!” she said, and then she laughed a rich, husky laugh.

I settled into the car, immediately noticing the scent of the upholstery’s leather mingling with the woman’s musky perfume. She was wearing a black and white dress that ended at the tops of her thighs, and she dangled a cigarette out the window. It wasn’t lit yet, and as she pulled back into traffic, she pointed to the lighter in the car and said, “Mind getting that for me?” When we came to a stop sign, she turned toward me and I held the lighter for her, trying to keep my hand from shaking as she inhaled.

“So what’s your name?” she asked afterward, blowing a plume of smoke out the window.

“Randy,” I said, trying not to stare too blatantly at her. She was gorgeous, but it was more than that. She was supremely confident, which was reflected in everything she did, from talking to driving to smoking. I was instantly smitten, but I didn’t think we’d do more than have a pleasant drive. Well, as pleasant as it could be with my hard on insistently throbbing inside my jeans.

But the situation immediately took a turn for the sexual. “Randy are you?” She chuckled. “You must get that a lot. I’m Stacy,” she said, then reached over and fondled my thigh, even though she still had her eyes on the road. Her hand was warm and seemed to say so much: that she was hot for me, that she wanted to take control of me, that she liked my body. No woman had ever been so forward with me, but I’d also never had an opportunity to be with anyone like her.

I stayed as still as possible while we chatted, not wanting her to interpret me moving my body as a sign that I didn’t want her to touch me. We pulled over to a rest stop after about an hour, and she asked me to get her some cigarettes. She pulled out a twenty and then stuffed it in the pocket of my jeans, her hand so close to my aching cock I nearly gasped. Stacy made it a point to admire my hard dick and whistled before she ushered me inside the service station.

“Is that your woman?” the clerk asked me while I fished the cash out of my jeans.

“Umm . . . not really. She’s just giving me a ride. But she’s hot,” I said, trying to sound knowing instead of like the nervous virgin that I was.

“Well, enjoy your ride,” he said, winking at me as he handed me the change.

I went back to the car to find her appraising me once again. I handed her the remainder of her cash, and she tucked it into her purse before having me light her another cigarette. The tension between us was palpable, and for once, a woman wasn’t expecting me to make the first move. She was so sophisticated she had a job in sales that meant she traveled often, sometimes internationally. She mentioned that she was staying in a hotel in Chicago and that her company was paying the tab. She didn’t say anything else even remotely suggestive for another hour, and it wasn’t until we arrived in the city that she finally made her move.

“Thanks for the ride,” I said, my heart pounding. “Can I pay you for the gas?”

“Yes,” Stacy said, then laughed as she ran a finger along my cheek. “But not in cash. I want this hot young body of yours. You could be a fun boy toy for the night. What do you think about that?”

“I’d be honored,” I said truthfully. “But . . . I’ve never done that before. I’m a virgin.” I felt the need to confess so she wouldn’t be disappointed by my performance, in case it wasn’t everything she was expecting.

“Well, aren’t I a lucky girl?” she uttered, sounding more pleased than surprised. I carried her bags inside the hotel and up to her lavish suite. I noted that the bedroom was bigger than my whole dorm room. “Now let’s see what’s hiding in those jeans,” Stacy announced, not wasting any time.

Before I knew it, I was totally naked, and she was kissing me, and then stuffing my cock into her mouth. I thought I might come right away, but she knew just when to back off to prolong our fun.

“That feels so good,” I told her, impressed with her cock sucking skills and her forthrightness.

“I’ve had some practice,” she noted with a laugh. “Now it’s your turn.” And then Stacy took her clothes off and spread out on the bed, opening her legs in invitation. Forgetting my shyness, I dove for her pussy like a starving man and was thrilled that she tasted as salty, sumptuous and impressive as I’d hoped she would. I’d heard some guys make comments about going down on girls that led me to believe it might not be a sexy thing to do, but after one taste of Stacy, I thought the exact opposite. That night I became a confirmed pussy eater, and I’ve never looked back. Girls are always impressed that I’m content to eat them out for an hour and not get tired or demand anything in return, but to me, it’s pure bliss.

As I energetically lapped at Stacy’s pussy, she shouted out instructions and moaned loudly whenever I hit the right spot. She helped out, too, pulling open her cunt lips and playing with her clit to show me exactly how she liked to get off.

Stacy came twice from my flicking tongue before she pulled me on top of her and demanded I slide my cock deep into her pussy. Her cunt felt like hot, wet velvet, and it surrounded my shaft with its sexy warmth. It was the most amazing sensation I’d ever felt. I was almost scared to start moving. I was worried I’d shoot off too quickly, but I got a handle on myself and started to fuck this beautiful older lady.

Stacy looked even more lovely up close. Her face was serene from her recent climaxes, and I stared deep into her eyes, feeling our passionate connection. She wrapped her legs tightly around my body, and we rolled around, trying different positions. We wound up with me pounding her from behind while she arched her back and bucked against me. Every move she made had my cock twitching inside her. Fucking a woman was nothing like jerking off, and it was even more exciting than anything I’d dreamed. When I finally came inside her for the first time, it felt so good that I almost wept. Afterward, we showered together and then feasted on each other’s body for the rest of the night. I couldn’t get enough of her, and I was sad when we had to part ways in the morning.

Stacy gave me her number and took mine, and the next time we saw each other was about a year later. By then, I’d fucked a few other girls, but she was still my dream woman. We’ve kept in touch since then, and every once in a while we hook up for old time’s sake.

I couldn’t have asked to lose my virginity to a hotter woman, and I’m so glad I had to hitch that day, or I’d have never found her.

Mr. Randy V., Via E Mail

HE AGREES TO SUBMIT TO THE BRUSH STROKES OF HIS MAKEUP ARTIST GIRLFRIEND

When I started dating Sasha, I was fascinated by her career as a makeup artist. She spends her days with models and actors, transforming them from hot to ultra hot, although sometimes she has to make them look older or younger, or even scary and disturbing. I’ve been on set and seen her work, and I’ve come to believe it is indeed an art. But I never thought that Sasha would one day use me as her canvas!

I’m an average looking guy, standing at five foot eight, with short brown hair and often a bit of stubble on my chin. I’m not exactly Brad Pitt, but I’m not what you’d call feminine or girlie. So when Sasha announced that she wanted to “practice” her craft on me, I looked at her like she was crazy. “Why me?” I asked. “Can’t you find a girlfriend for that?”

“Well, I just got these new colors,” she explained, “and I wanted to test them out. And . . . I think you’d look good with a little lipstick. Is that so wrong?” She looked forlorn, like she might cry, and I couldn’t have that.

“What exactly do you want to do? Make me into a girl?”

Sasha laughed at that suggestion. “Baby,” she said, grabbing my crotch and immediately giving me a hard on, “I could never turn you into a girl. I just think it’d be fun to put some makeup on you . . . and then kiss it off. Or fuck it off.”

As she stroked my cock, I couldn’t help but agree to her plan, especially after she got on her hands and knees and swallowed my dick. In between her oral caresses, she even let me outline her lips with a new red lipstick so that she’d look even sexier while she sucked me. Suddenly, I was looking forward to being prettified.

The next day at work, I couldn’t help getting distracted as I pictured Sasha’s face scrunched up in concentration as she decided on the right shade of shadow and the correct sort of lipstick for me. I was still a little uncertain about how I’d look after sitting in her makeup chair, but I knew that it made her and me horny. Besides, this was simply for us. It wasn’t like she was going to take photographs and show them to our friends.

When I got home that night, I found that Sasha had gone all out, cooking my favorite meal lamb chops, mashed potatoes and green beans and mixed a martini for me, just the way I like it. And she was wearing a lilac silk robe and nothing else. Sex was definitely in the air, and while we ate, she kept letting the robe fall open to show off her voluptuous body and perfect breasts. My hard on was obvious, but she didn’t pounce on it after I’d cleaned my plate. Instead, she led me into her “office,” aka the small space she uses for clients who aren’t outcalls.

“Are you ready?” she asked in a voice that told me she was more than ready herself. Her tone was more of a purring invitation than a question. When I nodded my response, Sasha draped a cloth over me and then told me to relax. I thought I’d done so, but she pressed her hands into my shoulders, massaging me gently, and then she stroked my cheek. “No, really. You have to be totally at ease or else it won’t work.”

“Okay, I’ll do my best.” I hadn’t thought I was nervous, but I guess I was. I sat and let my mind and body relax while she smeared lotions, creams and lipstick all over me. I was dying to sneak a peek at my newly glamorous image, but I didn’t, letting my girl do her thing. I found that the more I submitted, the more I appreciated the process. It was soothing.

Sasha hummed while she worked, and her sweet breath kept landing on my neck and cheek, while her breasts encased in a tank top pressed against me whenever she leaned forward. Feeling her body heat turned me on, and I wanted to grab her, push her against the wall and shove my cock into her.

After what felt like an hour but was really only half that time, Sasha instructed me to open my eyes. When I did, I had to blink them several times to be sure I wasn’t in some weird alternate universe. It was definitely me in the mirror, but I looked more feminine even beautiful. That’s what Sasha thought, too. “If I hadn’t just taken the time to do your lip gloss, I’d give you a giant kiss right now. I guess I’ll have to put my mouth to work in a different way,” she said, before sinking to her knees. Not only does Sasha give amazing blowjobs, she loves doing it. Sucking cock makes her wet I know from experience.

As she blew me, I thought about what it might be like for her to suck the pussy of a girl she’d just worked on. I stroked her hair and smiled, getting used to the feel of the gloss making my lips stick together. I didn’t feel like a girl, but I certainly didn’t feel like my usual self. I had entered into Sasha’s world and let her have her way with me. It felt like a type of submission, even as her hot, wet mouth was bobbing up and down along my hard cock. She pulled off of me to grin, her lips wet with saliva, and then said, “You’re gorgeous, but there’s one more thing I’d like to do after you come all over my face.”

I groaned, almost overcome with the need to spurt my load on her. “What’s that?” By that moment, she could have said she’d wanted to doll me up in one of her designer outfits and I’d probably have said yes. When she’s happy, I’m not only happy, but my cock is also guaranteed to be well taken care of.

“I want to paint your nails red. I want to see your femme hands roaming over my body, stroking my thighs, spanking my ass.” She licked her way from my balls up my shaft, letting her tongue trace circles along my cock as she awaited my reply.

“I’d be honored,” I said, because in that moment, I was. I realized that Sasha wasn’t thinking of me as just another client, and this wasn’t merely “practice.” She was seriously into it. She liked making me up, overtaking me with her brushes and powders. If it would get her wet to have me spank her while I wore nail polish, I’d do it. I guided my hand to the back of her head and pressed down, forcing her to swallow my cock even deeper. I was grateful for her moans of pleasure that treated my shaft to such indecent vibrations. Soon my spunk was filling her mouth, but my girl swallowed filling all and then gave me a kiss, getting some of my gloss on her lips.

After that, it was time for my manicure, which I also found comforting. She soaked my hands and then gave them a massage before applying a base coat to my nails. Then she seemed to draw out the action of my first manicure, slowly applying the candy apple red polish to each nail. Even though I still had my manly hands, they somehow looked more delicate. I thought of a woman spanking Sasha, and suddenly I wanted to spread my girl across my lap. But she was in charge, and she made me wait, blowing on my nails and then teasing me as she touched her pussy in front of me and forced me to watch.

“Sasha, you’re killing me! It’s not fair for you to tease me like that to show me your wet pussy and not let me touch it,” I complained, even though I knew I had to wait for my polish to dry. It was maddening being forced to wait like that.

“It’s tough being a girl, isn’t it?” she answered, laughing at my frustration. Unable to touch her, I got up and went to the full length mirror. I held up my hands and stared into my made up face. Some of my lipstick was smeared because we’d kissed so passionately, but I still looked like a more feminine version of me, and I’ll admit I was transfixed. Finally, after twenty minutes, my nails were dry, and then I sat on the bed and Sasha spread herself out on my lap. I normally give her light spankings, but this time, I spanked her hard, taking out my frustration at having to wait and my girl loved it! I’d never heard her make such noises.

I wasn’t sure if it was the strength of my smacks or if she was fantasizing about being spanked by a real girl, but I didn’t care. She liked me made up like this, and so did I. Only after her butt had turned a nice shade of pink did I let myself plunge my red lacquered fingertips into her juicy cunt. Seeing my newly feminized fingers entering her was so sexy. I was mesmerized and loved how slick she was. She came in record time, and I kept going, prompting a second orgasm from her. Then I had to fuck her, and by the time we were done, my makeup was history. But we’d both learned an important fact: While I’m still her man, I’m secure enough to enjoy a little color now and again.

Mr. Roger L., Baltimore, Maryland

HE LOVES THE SENSUAL APPEAL OF GIRLS’ CLOTHES AND LANDS HOT BABES WHILE WEARING THEM!

My foray into cross dressing began innocently enough. I had a very fashionable female friend who would sometimes hold things up against my body to determine if she should purchase them while we were out shopping. It’s not as unusual as it sounds, since she and I have a similar body type. I’m on the small side for a guy, and I never minded helping her out because I’d always found women’s clothing to be more interesting than men’s. The fabrics are much more sensual, and the colors are more vibrant and eye catching.

One day our shopping trip took an interesting turn. Angela had been admiring a silky purple top, but after holding it up against me and then looking at herself in a mirror, she decided that the color was much more suited to my skin tone. Her comment made me laugh until she suggested I try on the slinky garment. She stared at me, looking me directly in the eyes, and I have to admit that I felt a quiver of excitement upon hearing her risque suggestion.

I went into the dressing room and swapped my button down oxford for the purple top. (Luckily, we were shopping at the sort of hip boutique that didn’t mind a man trying on a feminine blouse.) The fabric was soft and sensual, and I thought the blouse was very flattering, much more so than my boring shirt. I nervously stepped out of the fitting room, wondering how my friend would react.

When I emerged, Angela clapped and even did a little dance. “You look amazing!” she said. “Doesn’t he?” she asked a passing saleswoman. I was all set to run and hide, but the lady ran a hand along my shoulder and down my arm, admiring how the garment hung on my frame.

“Yes, he does,” the woman said, and then she winked at me, which gave me a thrill. “My name is Dorothy, and I’d be happy to show you a few other pieces that might work for you.”

“Oh, that would be wonderful!” Angela blurted out happily. Then Dorothy put her hand on my shoulder and guided me around the store. She and Angela selected a number of elegant, classic pieces for me. Having two gorgeous women encouraging my transformation made my cock throb relentlessly. That day I left with a shopping bag full of girlie items. It was the first time I realized that dressing in female clothes was the ultimate turn on for me.

I became a very good customer at that store. I returned often, to flirt with Dorothy and have her show me the latest outfits as soon as they arrived. When I shopped, I often wore only a single piece of women’s clothing, like a blouse or a silk scarf, while keeping the rest of my clothes more traditionally male. When I was feeling bolder, I’d wear a dress or a dramatic looking hat. On those days, I’d walk around the mall and take note of people’s curious stares. I could sense that both men and women wanted to get to know the man who was brave enough to dress so provocatively for a trip to a suburban shopping mall. Their attention excited me, but I was even more thrilled to realize that I’d discovered a whole new side of myself.

When I donned women’s clothing even a single piece I felt changed, almost renewed. I felt calmer and more in control of myself, like a whole new world was open to me. That, even more than the ache in my cock, was what spurred me to keep dressing. My mild flirtation with Dorothy never amounted to more than that, but she was the first woman to show me that men can be sexy in women’s clothing.

I sometimes went online and browsed clothing sites, but that wasn’t the same as being in a store and touching the fabrics. Besides, it was next to impossible for me to tell what the garments would look like on me. I quickly realized that not having a woman’s natural curves made a big difference!

Through trial and error, I discovered stores that didn’t mind me browsing and trying things on. That was important to me because the whole experience of shopping was part of the fun. I liked being in a dressing room, knowing that naked women were also wiggling into their clothes just a few stalls away. Also, trying on women’s clothes under a spotlight, in front of those large three way mirrors, added to the glamour. I think of shopping for male clothing as chore, but shopping for ladies’ wear is always a special treat.

However, as much as I enjoyed wearing feminine clothing, I never expected women to be drawn to me while I was dressed en femme. But it seemed that the more risks I took with my wardrobe, the more girls were attracted to me. One of my favorite outfits seemed to turn a lot of ladies’ heads. It’s a low cut black blouse, a matching sequined skirt and fishnet stockings. One day when I was wearing it while shopping, a stunning redhead whistled at me as I passed her by on my way to a dressing room with an armful of clothes.

“Hot stuff!” she said, sounding very sincere. She was wearing a lovely cream colored knit dress that looked amazing on her curvy body.

“Thanks,” I replied, trying to gauge whether she was being friendly or wanted to know how hot my stuff really was.

I emerged from my dressing room a few minutes later in a cashmere sweater dress, wanting to get a look at myself in the big mirror in the hallway. And when I ran into the redhead again, my question was answered.

“Ooh,” she exclaimed, upon seeing me in the dress, and then she began petting me in a way that gave me no doubt to her intentions. “I like how this feels,” she said.

“I like how you feel,” I said as she let her hand trail down my arm, then along my hip. We were silent as things heated up between us. It was a weekday afternoon and the dressing room was empty, which made both of us act boldly. Her hands roamed my cashmere clad body and caressed my hard cock through the soft fabric. I let out a soft moan as she gently stroked my erection.

“I like that you’re not all woman,” she said. “Are you going to buy this dress?” she asked.

“Definitely,” I said, worried she was going to make me come from her sensual handjob.

“Good. Then maybe you can model it at my place? My name’s Brianna,” she said softly.

“Craig,” I said.

“Nice to meet you, Craig,” she said, kissing my cheek. My dick was throbbing relentlessly from her attention, but we resisted the urge to get it on in the fitting room.

“Go pay for your new dress, then you can wear it back to my place. I’ll give you a lift,” Brianna said.

Before long, we were sitting in Brianna’s car. But she seemed too mesmerized to turn the key in the ignition. Her own engine was already revving.

“You’re gorgeous,” Brianna said, and then she leaned over and kissed me while again stroking my dick through the cashmere, making it twitch. Brianna’s car was situated in a deserted corner of the mall’s parking lot, which made us feel more free to act on our illicit desires.

After we made out for a few minutes, Brianna began to work the dress up my hips, stroking my body through the fabric. The sensations of her hands and the soft cashmere rubbing against my skin nearly drove me crazy. I raised my hips up off the seat, so she could push my dress out of the way, and once it was bunched up around my waist, Brianna gave me one of the best blowjobs of my life. She was so turned on by my cross dressing that she was practically drooling. She swallowed my entire length, taking my cock deep into her hot, wet mouth and thrilling me with her lips and tongue. As she pleased me, I stroked her long hair and marveled at this turn of events. I had a feeling that if I’d been dressed like a regular guy when I ran into Brianna at the mall, she wouldn’t have given me the time of day.

“You better swallow all my come, Brianna,” I said breathlessly. “I don’t want to ruin my dress!” I was only partly serious her cock sucking skills were so fantastic, it would’ve been worth a trip to the dry cleaners but she obeyed me, swallowing every drop of my jizz like she couldn’t get enough of it.

Brianna got plenty more of my cream that evening because she took me home and dolled me up before fucking me all night long. She and I continue to see each other to this day, though we sometimes recreate our initial encounter, just for the thrill of flirting and cross dressing in public.

Mr. Craig G., Lexington, Kentucky

A GIRLIE SLEEPOVER ALLOWS A TV TO LET OUT HIS INNER LADY AND PLAY WITH HIS FELLOW FEMMES

My spine tingled as I felt the silk of my slip slide down my body, dropping into place as it fell past my hips. The lace hem swished against my legs as it settled, and I wiggled a bit to keep it in motion a moment longer, particularly enjoying the feel of the silk against my half hard cock. The other girls would be over soon for the party, and I still wasn’t finished dressing, so I had to hurry.

I pulled on my red wig, straightened it until it framed my face nicely, and then I ruffled the long layers, giving myself a tousled, just rolled out of bed look. Then I dabbed on a bit of concealer, a faint dusting of rouge, some mascara and a swipe of pink lip gloss. I was almost ready.

I stepped into a pair of glamorous high heeled slippers, the kind you see in old movies, with marabou trim. The slippers were cream colored, to match the cream lace on my pale pink slip. With one last twirl in front of the mirror to admire myself from every angle, I hurried to the living room, my heels click clacking on the hardwood floor as I went.

The doorbell rang at precisely the moment I reached the bottom stair, and I slowed my gait and straightened up a bit as I approached the door. My girlfriend, Arianna, was waiting on the other side, along with three friends, Ellen, Darcy and Claire. They were all wearing long coats, keeping their own sexy ensembles out of sight until they were safely inside the house, and each lady was carrying a different slumber party necessity: wine, ice cream, a large makeup case and a stack of fashion magazines I already had a pile of movies waiting next to the television.

As soon as the girls were inside, I took their coats and marveled at their lingerie. I knew Arianna would have no problem getting all dolled up, but I was still surprised that the other girls had agreed to the party at all, so I had no idea what to expect from their outfits. Apparently having a slumber party with a transvestite hadn’t caused them to rethink their racy lingerie, however, and I couldn’t help how my cock jumped under my nightie. I had a feeling I wouldn’t make it through the night without soiling my slip I only hoped the other ladies wouldn’t be put off by my excitement.

Like any other slumber party, the evening started with movies and snacks only instead of chick flicks, we watched x rated movies that featured pretty pajama clad porn stars. From the first scene, where a woman pranced around a pink bedroom wearing a short negligee and an itty bitty G string, I was hooked. I couldn’t turn away, and I hardly noticed the equally erotic women sitting around me, too caught up in the fictional version of our party to pay them any attention. It wasn’t until Arianna started giggling and summoning the other girls to “Look! Look at Nicole!” that I realized they were still in the room and that I was sporting a giant hard on. I blushed, embarrassed that my arousal was so obvious, but the girls merely giggled.

“Aww, isn’t she cute!” Darcy cooed, and I felt my face grow hot.

“She’s blushing!” Claire laughed, grabbing my cheeks and squeezing. “You don’t need to be shy in front of us,” she admonished. “Girls get aroused, too, you know.”

Well, I thought, this is what I asked for. I might as well man or woman up. I smiled at the other girls and laughed with them, trying to relax. It wasn’t working, though, and I was relieved when Ellen suggested we do makeovers for a while, since the movies were “a little too titillating for a girls’ night.” Makeovers sounded tame in comparison, and my cock needed a chance to cool down, so I happily welcomed the new activity. But as it turns out, real life makeovers aren’t nearly as mundane as I’d imagined.

I asked Darcy if I could do her makeup, and she pulled me onto her lap so that I was straddling her as I made her over. But as soon as she felt my burgeoning erection pressing against her, she pushed me off and called the other girls over. “Nicole seems really excited about the makeovers,” she informed them. “I think we should start with her!” The other three nodded their enthusiastic agreement, and I was pushed onto a chair as they all clamored over me with their makeup brushes and lipstick tubes in hand. Arianna stood over me, looking down as she skillfully applied a thin coat of foundation. Then Ellen was lining my eyes, Darcy rouging my cheeks and Claire painting my lips. I felt like a woman enjoying a spa day, getting pampered by so many gorgeous attendants, and my body relaxed completely as I allowed the women to have their way with me or at least my makeup. But I was also incredibly turned on by the makeover they were giving me, and I couldn’t quell the raging hard on that was throbbing under my slip.

Claire noticed my arousal, since she was sitting atop me, her chest pressed against mine as she told me to pucker and pout and blot. “Oh!” she yelped as her hot center made direct contact with my unyielding erection. “Ladies, I think Nicole needs the full treatment,” she said. “I feel a knot right . . . here.” And with that she reached between us, grabbed my cock and squeezed it lightly. My eyes popped open at her touch, and I saw the devious smile on her face, and then I heard the other girls’ murmurs of agreement. I had no idea what the “full treatment” was, but I had a feeling I was going to like it.

Darcy and Ellen filled their hands with lotion from a nearby bottle and started slathering it over my arms and legs, making my skin supple and soft and my cock rock hard. Arianna didn’t change positions she stayed behind me and started massaging my scalp, sending shivers down my spine. But it was Claire who was really getting me hot. She was still sitting on top of my erection, and she kept grinding against me, her boyshorts a minor barrier between us, since my slip had been forced out of the way by her movements.

I didn’t want to beg, but I was on the verge of an intense climax, and if I didn’t get inside someone soon, I was going to explode. Claire sensed that I needed a little more attention, though, and hopped up long enough to pull off her boyshorts before sinking into my lap again. This time, when my hard cock nudged her pussy, she shifted until it was flush with her opening and allowed me to slide between her wet lips.

As her drenched cunt swallowed my dick, I couldn’t help but wonder if girls always fucked during their slumber parties. Brief flashes of gorgeous girls in sexy nighties rushed through my mind, until I realized I was surrounded by the women from my fantasy and I was one of them, too! The idea further aroused me, and I started fucking Claire vigorously. Our hips slapped together and my slip rubbed between our bodies, the pressure especially delicious where her breasts were pressing against me. I’d never fucked while wearing any of my feminine trappings, and the sensation was so much more intense than when my partner was the one in the silky nightie. I truly felt like a lady who was fucking another lady. I wrapped my arms around her and pulled her closer, causing the silk to rub me more forcefully. The friction on my chest, and especially on my nipples, was all I needed to climax. I started to come and couldn’t stop. Claire continued riding me as I climaxed, and the other girls cheered us on.

Finally, Claire reached orgasm, too, and I collapsed back against the bottom of the couch. My cock was still hard, though, and the other girls were eyeing it mischievously. “Well, girls,” Arianna said, “I don’t think we’ll be doing much slumbering tonight!” And then she mounted me for her own ride. It was a short but explosive fuck, and the perfect way to end such an exciting evening.

For my first pajama party, I think it was a success. Next time, though, I want to have a pillow fight. It’s always been one of my fantasies to see a bunch of panty clad girls jumping around and swinging pillows at each other, with feathers flying everywhere, and now that I’m allowed at the girls’ sleepovers, I’m dying to join in such fun!

Mr. Nick H., Via E Mail