It started kind of strange. I am or at least was Len or Lenny – Leonard to my mother – a guy in my early 20s, kind of short and slender. I had a sister, Karen who was a few years older than me. She’d had a nasty breakup with a fiancé, and stayed with me for a while when she was trying to put her life back together.
It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a nice little brother, I let her have the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving little room for my clothes. Beyond that, we had to share one tiny bathroom, in shifts, since there was no way we were going to be in there at the same time – too small and too weird.
Karen stayed with me for about six months before getting her own place and moving out. Her place was smaller than mine, so while she took most of her stuff, she had more clothes than she had room for in the new place. She didn’t want to donate them, so she asked if she could leave them at my place until she could afford a bigger place. Again, being a nice brother, I let her do it.
Karen left behind all manner of things, skirts, dresses, blouses, bras, panties, shoes, makeup, and all that. After I while I got fascinated with it, which I guess was my first mistake. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.
I started by just touching her clothes while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my head while doing myself. After a time, that didn’t turn me on the way it once did, so I even began putting on some of her clothes. That seemed to be a bigger turn-on and her clothes seemed to fit, since we were almost the same size.
As time went on, I’d dress up completely in Karen’s clothes for my self-abuse sessions, and even left them on after I’d cum. I began to play with it all a little bit and even began to use some of the makeup she’d left behind. I’d pad her bras with socks or whatever, put on panties, a skirt, blouse, and shoes, then brush my hair in a more feminine style and learned how to do my makeup.
It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no girls willing to help me. Before long, I’d come home from work, dress up all girly, and prance around my apartment before getting myself off. I’d even wear one of Karen’s old nighties to bed afterward.
I had a few friends who I’d hang out with occasionally. One of them, who I’d known since high school was Matt. He was always the popular sort, never had any problem getting girls, and often seemed to have one or more hanging off him. He’d take me along as a wingman sometimes, though I never managed to get any girls out of it.
One night he and I were drinking, and I’d had more than I should have, and we began talking. He started telling me about how he got some chick to let him finger her in public in a restaurant. He said they’d also gone to a movie theater, sat way in back, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.
“Hey, Lenny, what’s the kinkiest thing you’ve even done?”
“Shit, Matt, I can’t get girls to do ordinary shit with me, much less anything kinky.”
“Come on, guy, you must have done something just a little bit out there.”
As I said, I’d had too much to drink, and I confessed to dressing up in my sister’s clothes to jerk off.
“Seriously, Len. Do you just slip on her panties to get turned on or do something more?”
“Sometimes I’ll go full drag, clothes, shoes, makeup, and everything.”
“Fuck, man, that I’d like to see.”
“I don’t know, dude. Nobody has ever seen me that way. I’d be freaked out to have someone see me.”
“Come on, Lenny. You know me. Let me see you dressed up, just one time.”
“Matt, if anyone ever found out, I’d be totally screwed. I’d have to leave town.”
“Lenny, I swear to God, I’ll never tell anyone.”
That was Thursday, and it was already late and I was too drunk and had to work the next day. He asked if I’d dress up for him the next night. I agreed and told him to come by after work on Friday, but to give me some time to get ready.
“Lenny, do you think you can be ready in an hour?”
“I think so. I get home about six, so come by my place around seven.”
The next day I really had some regrets about agreeing to let him see me dressed up. I called him during lunch and tried to back out, but he said I’d promised and he expected me to keep my promise. I was on edge all afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented body wash, shaved my face, legs, underarms, and body.
I almost felt like I was going to cry, I was so humiliated at the thought of having this guy see me in my sister’s clothes. I dried my hair and styled it girlish, then put on panties, a bra, a nice skirt, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye shadow, lipstick, and of course I painted my toenails and fingernails.
I wore some low heels with open toes, to show off the toenail polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o’clock. My knees were wobbly as I walked to the door. I looked through the peephole and sure enough it was Matt. I opened the door and let him in.
Matt was gaping and staring as he walked in my place. I closed and locked the door and he turned me around then stepped back to take a good look at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me nervous. He came back in front of me and grabbed me gently by the shoulders.
“Damn, that is hot, girl.”
“I’m not a girl, I’m just dressed like one. I’m Lenny, you know that.”
“The way you look, Lenny doesn’t work. How about I call you Lynn?”
“Okay, Matt, you got to see me, now let me change back.”
“Hold on, Lynn, not so fast. Don’t run off on me already. Come sit on the sofa with me.”
“I don’t think we should do that, Matt. I’m not one of your little girlfriends, I’m Lenny.”
“While you’re like this, you’re Lynn, and I like Lynn. Come on, please sit on the sofa with me.”
“This was a mistake. I shouldn’t have done this. I want to change.”
Matt put and arm around me tight and walked me over to the couch, pulling me down beside him there. He had his arm around my shoulders and seemed to be getting way too much pleasure out of this.
“Lynn, baby, you are one hot fox.”
“Matt, this feels really weird.”
“Not weird, Lynn, just a little kinky, baby.”
“No one has ever seen me like this before. I feel uncomfortable.”
“You shouldn’t be uncomfortable. You look wonderful, one of the sexiest girls I’ve seen in a while.”
“You’ve got lots of girls – real girls, not fake ones, like me.”
“Don’t tear yourself down. Most of those girls have nothing on you.”
“Jeez, now you’re really embarrassing me.”
“Let me take you out to dinner, Lynn”
“Just let me change into some normal clothes, Matt.”
“No, babe, just like this.”
“God, I can’t go out in public like this.”
“Sure you can, baby. You look absolutely stunning.”
“What if someone sees me – recognizes me?”
“No one will recognize you as that nerdy guy.”
“Doesn’t it bother you to be out in public with a guy in drag?”
“No one but you and I will know, and besides I like a little bit of kinky sometimes.”
“I don’t know.”
“Come on, Lynn. A nice dinner, and I’ll treat you the way a lady should be treated.”
“That makes me feel really weird.”
“And maybe a little turned on?”
“I don’t know if we should be doing this.”
“I do, and we should.”
With that, Matt got up and drew me to my feet. He wrapped his arms around me and pulled me close. I think my eyes were the size of saucers and my knees were getting weak as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the door. When we got there, he stopped and turned.
“Do you need a purse, keys, and such?”
“I think Karen left a couple of purses here too.”
“Grab one and your keys and let’s go.”
This was already getting way beyond anything I’d ever intended, and I was really afraid of where it was going to go. Matt went with me in the bedroom, and I went in the closet and found a purse that didn’t look too bad with what I was wearing. I took my keys and wallet and dropped them in the purse before turning to Matt.
“I’m really not sure we should be doing this, Matt.”
“Everything is going to be just fine, Lynn.”
Matt actually had money, which is yet another reason why most of the girls fell all over each other to get to him. We went downstairs to his brand new blue BMW Z4 convertible and he opened the door of the car for me. I managed to sit down in a somewhat ladylike fashion – I don’t think I showed too much. He got in and drove us to a very nice restaurant.
He used valet parking and walked me in, holding the door for me. I still felt weird as shit, but just tried to ignore how I looked and enjoy myself. Matt ordered a nice bottle of wine for us, and I really needed something to drink. I downed my first glass before he’d taken more than a couple sips of his wine. Matt poured me another glass, but I took it a little slower.
The waiter seemed very taken with me, and when he thought I didn’t notice, tried looking down my blouse. Several other men seemed to notice me, which made me squirm in my seat. One guy who works with Matt stopped at the table to talk with us. I’d met him several times before, but he clearly didn’t recognize me.
“Well, Matt, who is this beautiful lady with you tonight?”
“This is my date, Lynn. Lynn, meet Oliver, he ‘s another department manager where I work.”
“I’m so pleased to meet you, Oliver.”
“And I’m very pleased to meet you, Lynn. Matt is clearly a very lucky man. But if you want a change of scenery, give me a call, I’d love to show you a good time.”
With that, Oliver handed me a business card. I think I turned red, but slipped it in my purse.
“Thanks, Oliver, but I’m not really looking for anyone else at the present.”
“Well, Matt, if you get tired of Lynn here, feel free to send her my way.”
Oliver bent down and kissed my cheek before walking off.
“I do not fucking believe that.”
“I tried telling you, Lynn. You are one hot chick. Half the men in this place would dump their date for a chance to take you home.”
“That’s only because they don’t know what I really am.”
We had a lovely dinner and I continued to drink way more than I should have. This whole scene had blown my mind so much I didn’t know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to talk to Matt. We finished dinner and I thought Matt would take me back to my place.
“Lynn, honey, it’s still early, why don’t we go dancing?”
“Are you sure about that?”
“You’re taking a walk on the wild side, just take a bit longer walk.”
Matt wouldn’t take ‘no’ for an answer and drove us to the hottest club in town. This was the sort of place that would never let the likes of me inside. They must have had a hundred people lined up waiting to get in. Matt was obviously pretty well known, and he walked us up to the front, and we were waved in, though I noticed he slipped the guy some money.
We went in and got a drink and then Matt wanted to dance with me. I felt strange as shit, but it was a fast number and I was already half plastered so I went out to dance with him. We danced several fast dances, then a slow number came on. I thought we’d go sit down, but instead, Matt pulled me close to him to dance.
He had one hand on my upper back, holding me tight, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that Matt had a hard-on as he did that. That scared me more than a little, but I wasn’t sure what I could do. I felt helpless as we danced. When the number ended, Matt stopped, held me tight, and kissed me.
My knees got so weak that if he hadn’t been holding me tight, I’d probably have slumped onto the floor. He gave me a long kiss, and to my surprise, I began to kiss him back. I felt conflicted – I didn’t feel like I should be doing this, not with a guy, but I seemed to be enjoying it. We kissed for a minute before he walked me back and we had another drink.
I’d been drinking pretty good before, but I didn’t slow down. I was half afraid of what was going to happen, and felt like I needed to be very drunk. We drank more and danced more, and the more we drank and danced, the more Matt kept feeling me up and kissing me. My mind was blown – Matt knew I was a guy dressed like a woman, yet he was acting like I was the real thing.
As I said, I’d been Matt’s wingman more than a few times, and had seen him this way with women many times before. I also knew that in most cases he ended up taking those women home and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don’t know how long we danced and drank, but by the time Matt was ready to leave, I was really plastered.
I thought Matt was going to drive me back to my place, but instead he drove me to his apartment. As I said, Matt had money, and he had a very nice two bedroom apartment – nice furniture and all that. Part of me hoped that he was going to let me crash in the spare bedroom. Another part of me wanted anything but that.
“Matt, I really need to get home and change.”
“Lynn, honey, there’s no hurry. Just relax and enjoy your walk on the wild side.”
Matt got us each a drink, like I needed any more alcohol, and sat me down on the sofa, sitting right alongside me. Matt put his arm around me and pulled me tight, then began to kiss me. He started just with the lips, then added in some tongue, while feeling up my ass and my fake boobs. I seemed to be enjoying it, but felt that it was wrong.
“Matt, we shouldn’t be doing this.”
“Sure we should. You seem to like it, and I told you I occasionally like kinky shit.”
“I don’t know if I’m ready to go any farther.”
“Lynn, baby, I’ve shown you a good time. I’ve made you feel good. You seem to be getting into this. Can’t you help me feel good too?”
“What… What did you want me to do?”
“If nothing else, can you at least go down on me?”
“You want me to…?”
“Please, Lynn, baby.”
Matt kissed me and stroked my ass as he unzipped his pants with his other hand. He pulled out his cock, which was already hard and standing straight up. He kissed me again, then gently pushed my head down toward his prick. I got close and looked at it. It was long and hard and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the head of his dick between my lips.
Matt moaned and leaned back, still keeping a hand on my head. I let the head of his cock slip from between my lips, before taking it back and going just a little farther with it. I bobbed up and down on his prick, gradually taking it deeper and deeper into my mouth. I’d never had a dick in my mouth before and it felt strange, but in another way, it felt very natural.
I slowly but steadily fucked his cock with my mouth and Matt seemed to like it. Some precum came from the tip, and it had a salty taste, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the base of his dick as I sucked the rest of it. By now, Matt was moving his hips, almost fucking my mouth, as he held my head tight.
Matt moaned loudly and got very rigid as his cock erupted in my mouth. He held my head with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for breath, though it took a couple of swallows to get it all down. It gradually eased and I cleaned his dick off as I pulled my head back from it.
Matt pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my mouth as we kissed, but that didn’t seem to bother him. Matt continued to kiss me and I didn’t even realize it as he pulled my skirt up over my ass and began to caress my ass through my panties. He even snuck his hand into my panties and fondled my bare ass.
I don’t know why I didn’t notice, I don’t know why I didn’t stop him. Maybe I was enjoying it all too much, and maybe I was just too drunk. Before I even realized it, Matt had removed my skirt and blouse and was carrying me into his bedroom. I was so far gone at this point I didn’t know or care, or maybe it was what I really wanted.
“Lynn, baby. You are wonderful and beautiful, and I love what we’ve done, but I need to fuck you.”
“Do it, Matt. Do it.”
Matt set me down on his bed on my hands and knees and pulled down my panties. My cock, which had been ignored for so long sprang to attention, but Matt was interested in other things. He took off his pants and shirt and got in bed behind me. He reached into a drawer in the table beside the bed and got a tube of lube.
Matt rubbed lube over his prick, then onto a finger which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able to move it pretty freely after a minute or two. He snuck a second finger in and began to finger fuck my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the back of my neck as he pulled his fingers out of my ass.