It started variety of strange. I am or at to the lowest degree was Len or Lenny - Leonard to my mother - a guy in my betimes 20s, kind of curtly and slender. I had a sister, Karen who was a few years older than me. She'd had a cruddy breakup with a fiancé, and stayed with me for a patch when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one chamber topographic point, and not all that big. Being a nice little brother, I let her bear the bed, while I slept on the sofa. She had a ton of wearing apparel and more than than filled my wardrobe, leaving little elbow room for my dress. Beyond that, we had to plowshare one tiny bathroom, in shifts, since there was no way we were going to be in there at the Saami time - too small and too weird.

Karen stayed with me for about six calendar month before getting her own piazza and moving out. Her stead was smaller than mine, so while she took most of her stuff, she had more dress than she had room for in the new shoes. 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.

Karenic left behind all manner of thing, skirt, dresses, blouses, bandeau, panty, shoes, constitution, and all that. After I while I got fascinated with it, which I guess was my showtime error. I started by just touching some of the apparel. 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 dress 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 metre, 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 metre went on, I'd arrange up completely in Karen's clothes for my self-abuse Roger 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 constitution she'd left behind. I'd pad her brassiere with socks or whatever, put on panty, a annulus, 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 function of self-stimulation. hell, I needed to get off too, and there were no girls leave to help me. Before farsighted, I'd come house from work, dress up all girly, and strut around my apartment before getting myself off. I'd even wear one of Karen's old nighties to bed afterward.

I had a few champion who I'd hang out with occasionally. One of them, who I'd known since high schooling was flatness. He was always the popular sort, never had any problem getting girls, and often seemed to bear one or more hanging off him. He'd acquire 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 induce, and we began talking. He started telling me about how he got some skirt to let him finger her in public in a restaurant. He said they'd also gone to a moving picture theater, sat way in back, and she hiked up her bird, sat on his lap, and fucked him in the theater during the movie.

"Hey, Lenny, what's the way-out thing you've even done ?"

"Shit, Matt, I can't get girlfriend to do ordinary poop with me, much less anything kinky."

"seed on, guy, you must have done something just a little bit out there."

As I said, I'd had too much to drink in, and I confessed to dressing up in my sister's clothes to jerk off.

"Seriously, Len. Do you just slip on her pantie to get turned on or do something to a greater extent ?"

"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 stimulate someone see me."

"Come on, Lenny. You know me. Let me see you dressed up, just one time."

"matte, if anyone ever found out, I'd be totally screwed. I'd have to result town."

"Lenny, I swear to God, I'll never tell anyone."

That was Thursday, and it was already late and I was too fuddle and had to solve the next day. He asked if I'd dress up for him the next night. I agreed and told him to fare by after work on Fri, but to reach me some clip to get ready.

"Lenny, do you imagine you can be ready in an hour ?"

"I think so. I get abode about six, so come by my situation around seven."

…………………………………………………………………………

The next day I really had some rue about agreeing to let him see me dressed up. I called him during lunch and tried to second out, but he said I'd promised and he expected me to keep my hope. I was on sharpness all good afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with odoriferous body wash, shaved my grimace, leg, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the thought process of having this guy see me in my babe's dress. I dried my whisker and styled it girlish, then put on panties, a bra, a courteous bird, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on fundament, then some stress, eyeliner, eye trace, lipstick, and of course I painted my toenails and fingernails.

I wore some low dog with clear toes, to evince off the toenail polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly recite when I looked in the mirror. I was still shaking and uneasy 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 as shooting plenty it was Matt. I opened the door and let him in.

flatness 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 aspect 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 straw man of me and grabbed me gently by the shoulders.

"shucks, 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 ?"

"okeh, matt, you got to see me, now let me alter back."

"detainment on, Lynn, not so fast. Don't run off on me already. ejaculate sit on the sofa with me."

"I don't think we should do that, matte. I'm not one of your little girlfriends, I'm Lenny."

"While you're like this, you're Lynn, and I like Lynn. seminal fluid on, please sit on the couch 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 shoulder and seemed to be getting way too much pleasure out of this.

"Lynn, sister, you are one hot fox."

"mat, this feels really weird."

"Not weird, Lynn, just a minuscule 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 miss I've seen in a while."

"You've got great deal of girls - literal girls, not fake I, like me."

"Don't tear yourself down. Most of those girl have nil on you."

"Jeez, now you're really embarrassing me."

"Let me take you out to dinner, Lynn"

"Just let me exchange into some normal clothes, Matt."

"No, babe, just like this."

"God, I can't go out in public like this."

"Sure you can, coddle. You look absolutely stunning."

"What if mortal 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 puff ?"

"No one but you and I will know, and besides I like a piffling 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 conclusion. I think my eyes were the size of dish aerial and my genu were getting weak as he leaned forward and kissed me on the face. He let go with one arm and walked me to the door. When we got there, he stopped and turned.

"Do you need a handbag, paint, and such ?"

"I think Karen left a match of purse here too."

"catch one and your headstone 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 bedchamber, and I went in the closet and found a bag 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 amercement, Lynn."

Matt actually had money, which is yet another reason why well-nigh of the girls fell all over each other to get to him. We went downstairs to his brand new risque BMW Z4 exchangeable 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 doorway for me. I still felt unearthly as prick, but just tried to ignore how I looked and relish myself. Matt ordered a nice bottleful of wine for us, and I really needed something to pledge. I downed my first glass before he'd taken more than a distich sips of his wine. Matt poured me another glass, but I took it a picayune slower.

The server seemed very taken with me, and when he thought I didn't notice, tried looking down my blouse. Several other men seemed to find me, which made me squirm in my tail end. One guy who works with matte stopped at the table to talk with us. I'd met him respective times before, but he clearly didn't recognise me.

"Well, matt, who is this beautiful gentlewoman with you tonight ?"

"This is my date, Lynn. Lynn, meet Oliver, he ‘ s another department manager where I work."

"I'm so please to meet you, Oliver."

"And I'm very please to meet you, Lynn. lustrelessness is clearly a very prosperous man. But if you want a variety of scene, give me a song, I'd love to evince you a good time."

With that, Oliver handed me a business card. I think I turned red, but slipped it in my purse.

"Thanks, Joseph 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 transmit 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 ditch their date for a chance to take you home."

"That's only because they don't know what I really am."

We had a pin-up dinner party and I continued to drink way Thomas More than I should have. This whole fit had blown my judgement so very much I didn't know what else to do. A few former 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 party 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 slope, just take a bit longer walk."

Matt wouldn't take ‘ no'for an answer and ride us to the live ball club in Town. This was the variety of place that would never let the ilk of me inside. They must have had a c 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 boozing and then matt wanted to trip the light fantastic with me. I felt unknown as horseshit, but it was a profligate number and I was already one-half plastered so I went out to dance with him. We danced several fast dance, then a slow identification number came on. I thought we'd go sit down, but instead, lustrelessness pulled me come together to him to dance.

He had one hand on my amphetamine back, holding me smashed, as his other helping hand came down on my ass. He began to fondle my ass, which made me wriggle. I could feel that Matt had a erection as he did that. That scared me more than a little, but I wasn't certain what I could do. I felt helpless as we danced. When the number ended, Matt stopped, held me tight, and kissed me.

My articulatio genus got so weak that if he hadn't been holding me soaked, I'd probably have slumped onto the floor. He gave me a long buss, and to my surprise, I began to snog him back. I felt contravene - 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 swallow.

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 to a greater extent, and the more we drank and danced, the more than Matt kept feeling me up and kissing me. My mind was blown - Matt knew I was a guy dressed like a charwoman, yet he was acting like I was the real thing.

As I said, I'd been lusterlessness's wingman more than a few times, and had seen him this way with women many times before. I also knew that in to the highest degree font he ended up taking those women base and fucking them. That scared me, but also seemed to wrick me on, and it scared me that I was turned on by it. I don't sleep together how foresightful we danced and drank, but by the time lusterlessness was gear up to pull up stakes, I was really plastered.

I thought Matt was going to drive me back to my place, but instead he drove me to his flat. As I said, Matt had money, and he had a very skillful two bedroom apartment - nice article of furniture and all that. persona of me hoped that he was going to let me gate-crash in the trim sleeping room. Another contribution of me wanted anything but that.

"Matt, I really want to get home and change."

"Lynn, love, there's no haste. Just relax and revel your manner of walking on the savage side."

Matt got us each a drink, like I needed any more alcohol, and sat me down on the sofa, sitting right alongside me. lustrelessness 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 cook titty. I seemed to be enjoying it, but felt that it was wrong.

"flatness, 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 make to go any farther."

"Lynn, child, I've shown you a unspoilt prison term. I've made you feel practiced. You seem to be getting into this. Can't you serve me sense dear too ?"

"What… What did you desire me to do ?"

"If nothing else, can you at to the lowest degree go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

Matt kissed me and stroked my ass as he unzipped his bloomers with his other handwriting. He pulled out his cock, which was already laborious and standing straight up. He kissed me again, then gently pushed my forefront 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 school principal of his shaft between my lips.

Matt moaned and leaned back, still keeping a deal on my oral sex. I let the head of his cock slip from between my sass, before taking it back and going just a little farther with it. I bobbed up and down on his prick, gradually taking it recondite and deeper into my lip. I'd never had a dick in my mouth before and it felt unknown, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my lip and Matt seemed to like it. Some precum came from the tip, and it had a salty gustatory modality, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the substructure of his pecker as I sucked the residuum of it. By now, Matt was moving his pelvic girdle, almost fucking my mouth, as he held my headspring tight.

Matt moaned loudly and got very rigid as his cock erupted in my mouth. He held my question with both hands as he emptied his ball into my pharynx. I swallowed his cum and gasped for breathing space, though it took a couple of swallows to get it all down. It gradually eased and I cleaned his peter off as I pulled my heading 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 discommode him. mat continued to osculate me and I didn't even realize it as he pulled my doll up over my ass and began to caress my ass through my step-in. He even snuck his hand into my panty 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 a lot, 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 manage, or maybe it was what I really wanted.

"Lynn, sister. 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 work force and knees and pulled down my panties. My cock, which had been ignored for so longsighted sprang to attention, but lustrelessness was concerned in other matter. He took off his pants and shirt and got in bed behind me. He reached into a draftsman in the table beside the bed and got a tubing of lube.

matte rubbed lubricant 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 back finger in and began to feel fuck my ass, and in spite of myself, I began to bed him back. Matt leaned down and kissed the book binding of my cervix as he pulled his digit out of my ass.

I felt the headland of his cock at my son of a bitch and tensed for just a second before relaxing. At this point, I think I wanted him as much as he wanted me. I felt the header get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but flatness took it prosperous and slow at first, until I really started to get into it.

I soon felt his hips slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy fuck my ass, I'd have thought you were crazy and told you to leave me the fuck alone. Now matt was fucking me and I was in heaven. I felt his cock slide oceanic abyss in me and fill me up. It turned me on in way I'd never have expected.

Matt slid his dick in me so far, I could almost sense him jab my belly. I'd almost swear I saw my tummy bulge as he got all the way in. In spite of whatever reservation I'd had, I was loving every second of this, every accident of his cock. I wanted his peter in my ass, and when he came with a gush in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our position, with his pecker still inside me. I was on a sexual highschool and wanted nothing more than to keep feeling his dick in my ass. His dick was getting soft, but I wanted to continue him in me as long as I could. As we came off our high-pitched, Matt began to stroke my shoulders and osculate the back and side of my neck.

"Lynn, baby, you are beautiful, aphrodisiac, and wonderful, and I just wish I could stay put inside you forever."

"I wish you could stay inside me forever too. I'm yours whenever you want."

"I just might hold you to that, Lynn, baby."

Essentially, Matt was spooning me as we lay there in his bed with his putz slowly easing its way out of me. I moved my ass back, trying to save as a good deal of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the next daybreak with Matt still spooning me and with his gruelling putz pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's hard putz against my ass, I'd have leapt from bed and mystify out of the elbow room as fast as I could. Instead, I moaned and moved my ass around against his prick.

mat woke up and began stroking me and kissing the back of my neck as he eased around so his prick was up against my arsehole. I could sense it and wanted it back inside me. I reached around, grabbed his prick and guided it into my ass, as we lay on our sides. It was a gentler fucking, instead of the throb that we had at the end finis night, but I still loved it.

My shaft got hard as I felt his filling me up. It was a slow leisurely fuck, almost loving, and I reached behind me to stroke Matt's body as he fucked me. He pressed tight against me as he came deep in my ass. I couldn't believe how much I enjoyed having this guy fuck me, but I knew I wanted it to continue as long as he wanted me.

"Lynn, baby, thank you for last Nox, and for this aurora too."

"I hope we'll have more than just last night and this morning."

"If that's what you want, we don't have to quit with one date."

"I want it. I want your cock in my ass, in my oral cavity, wherever you want, and whenever you want."

"I want Lynn. I don't want Lenny."

"I never thought I would, but for you, I'll be Lynn."

"What happens to Lenny ?"

"Lenny has a job, and I don't think they'd appreciate Lynn showing up in place of Lenny. I need to be Lenny at work."

By then, Matt's cock had slipped out of my ass and I'd rolled over confront Matt. I kissed lusterlessness, and he kissed me back and began stroking my body. We spent a hanker clock time kissing and touching each other before we got up and went to the exhibitioner together. Without my dress, my bra, my step-in, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his cock, I got down on my knees and sucked him off again. With my makeup off and tomentum wet, I didn't look quite the same, but I dried my tomentum, styled it as best I could and got dressed in my wearing apparel from last night. I had a trivial makeup in my purse and could do lipstick, eyeliner and a little base, to make me more like Lynn.

The more I looked like Lynn, the more mat seemed to be warm. He fucked me once more before taking me home, and we made a date for that evening.

When I got home, I looked at myself in the mirror, then just slumped onto the couch and shake my head. I could feel Matt's cum leaking out of my ass as I sat there. Who was I ? Was I Len or Lynn ? Who did I want to be ? I wasn't sure, but guessed I'd have to crop it out along the way. For now, at least, I guess I was Lynn, until lusterlessness got tired of me or I got tired of it all. I hazard Karen's spear carrier clothes were now Lynn's wearing apparel till far notice.

Matt took me out again Sabbatum Night, and took me back to his station. We were not as tired or drunk and after I went down on him, he fucked me three multiplication. I enjoyed it but as I drifted off to sleep, I was starting to sense infringe. Was this really how I wanted to live out my life ? And how farseeing was matte likely to be interested in me ?

We fucked a duad more times the succeeding sunrise and I went home. I decided that Lynn would only be on Friday and Saturday nights. I was going to live and work as Lenny, the rest of the time. It was hard. We all want to be appreciated. We all want someone to conceive we are special. Lenny is n't special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as matt 's wingman. lustrelessness always found an attractive char to assume household. I was a little jealous - both of Matt and of the woman. On rare social occasion, I 'd be Lynn during the week, and Matt would come in to my place to fuck me. Usually Lynn was a weekend matter, but some weekends, Matt had other plans.

... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ..

One Fri night, Matt and I were at a golf club and I was being Lynn, though Matt seemed to be giving most of his attention to a very pretty blonde. I sat there feeling pretty neglected, when Nicole came up to talk to me. Nicole was a brunette, about my age, a bit taller, but with a very nice frame, b-cup boobs, and a pretty face.

'' Well, honey, your escort seems to be ignoring you. ``

'' I guess I 'm old news. ``

'' dopy guy. If you were mine, I would n't dump you like that. By the way, my public figure 's Nicole. ``

'' Hi, Nicole. I 'm Lynn. And flatness and I have kind of an strange relationship. ``

'' fountainhead, your guy appears to be about fix to tread out with another woman. Would you ingest any interestingness in doing the same ? Or are you strictly into guy wire ? ``

'' You mean ... you 're concerned in women ? ``

'' I like cleaning woman. I like men. And sometimes I straddle the line. ``

'' What do you stand for by straddling the line, Nicole ? ``

Nicole reached up, and stroked my nerve. I 'd shaved as cleanly as I could before going out with Matt, and my facial fuzz is not stocky, but there was the slim trace of very dismount stalk and I could order by her manifestation that she felt it. Nicole leaned forward and kissed me.

'' Well, Lynn, something Tell me that you straddle the line. ``

'' And you like that ? ``

'' Let 's dance a bit, honey. After all, your guy seems to be diverted elsewhere. Unless, of course you 're not into fair sex. ``

'' I like women, I 'm just ... ''

Nicole took my hand and led me out onto the terpsichore floor. I glanced back at Matt and he was so fixated on the blonde that he never even noticed that I left. We did a couple of fast dances, and I really enjoyed dancing with Nicole. hell, as Lenny, I had trouble getting char to even trip the light fantastic toe a good deal with me.

A slacken phone number came on and Nicole grabbed me and pulled me end. She put one hand in the middle of my back and the other one down over my ass. I giggled and squirmed as she caressed my ass through the dance. I glanced around and no one seemed to even notice us or what we were doing.

At the end of the dance, Nicole gave me a buss that almost buckled my knees. I could find my dick getting hard and barely being restrained by my panties. My mind was blown. We stood there kissing for I'm not even sure as shooting how long. I'd never had a woman buss me like that before, and I was in no rushing for it to end.

We went back to get a drink, and mat appeared to be gone, as did the blonde he'd been flirting with. It bothered me, but at the Lapplander clock time, it didn't bother me that a lot. I wasn't sure that I wanted a long condition relationship with Matt, and he seemed to still be pretty much sleeping around. Besides, now Nicole seemed to be interested in me, or at least I hoped she was.

"fountainhead, Lynn dearest, it looks like you lost your guy."

"Well, I guess I don't judgment, at to the lowest degree as long as I have you for company."

"Are you sure that's what you want, Lynn ?"

I leaned forward and kissed Nicole, and she returned my kiss. We finished our drinks, danced a bit more then Nicole invited me back to her spot. Nicole was an within sales rep for a tech company. She worked near where I did and made some decent money. I was still amazed that she had any interest in the likes of me.

"Are you sure that's what you want, Nicole ?"

"I know your appearance belies what you have down below, but I'm full with that. As long as you like little girl, I think we can have some fun."

"I like girls, I just never had practically lot before."

"So maybe you never met the flop daughter before. As long as you're open minded and flexible, I think we can possess lots of fun."

I felt a little uncertain. Nicole was pretty and she seemed leave. I just didn't understand why she'd have any interestingness in me - not after knowing that I was a guy dressed as a girl who'd been out with a guy. Look, I'd never had any woman unforced to give me the time of day, much less get confidant with me. Nicole figured out what I really was and still seemed occupy. Now that was kinky.

Matt had left me and gone off. I could either call an Uber or find out what Nicole had in mind. Honestly it was probably ripe than what flatness had done, even though I seemed to enjoy fucking flatness. I sat for several seconds, just pondering the possibilities. I looked at Nicole who sat there with a short puzzling grinning on her case, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walking on the risky slope anyhow, why not walk a little farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the golf-club. She had a car nearby, cypher as expensive or flashy as Matt's BMW, but a Nissan 370Z a couple of year old. It was certainly nicer than my eight year old Civic. Nicole opened the car door for me, which surprised me a bit. Yes, Matt had been doing the same, but Nicole was a cleaning woman and knew what I was down below.

I stood slightly puzzled for a second before smiling at her and sitting down in a ladylike fashion. Before she closed the car door, Nicole leaned over and kissed me. She came around, sat down in the driver's seat and started the car. Before she put it in gear, she smiled at me again and gave me a quickly kiss.

"We'll go to my spot, Lynn, unless you have an objection."

"Charles Herbert Best offer I've had in a long time."

"Better than your little boyfriend ?"

"No question."

We were stopped, getting ready to die the parking lot. I leaned over and gave Nicole a kiss. She smiled and stroked my head, before taking us out on the road. She drove us a few miles to her flat. It was on the second base and we had to walk a flight of step, but we had our weapon around each other, giggling and petting each other as we went.

Nicole had a nice little one bedchamber stead, clearly feminine, with a tone down flowered sofa and chairs, along with some art prints on the walls. The mark were largely of women and men, along with a few where it wasn't quite clear if it was manful or female. She walked me over and we sat on the sofa, and she put her arm around me.

"So when did you substantiate that you were Lynn ?"

"I really just started dressing up in my Sister's clothes as a turn-on. I told flatness one time when I was wino and he wanted me to coiffe up for him."

"Obviously, you did."

"He liked the way I looked and wanted to assume me out dressed like that."

"Had you never gone out dressed that way before ?"

"Oh my God, no. Even now, the only time I go out this way is with him."

"But you were into Guy ?"

"I didn't think so, until he took me out as Lynn, then took me home and fucked me."

"wealthy person you been with any former guys than him ?"

"Never. Most of the fourth dimension, I'm Len or Lenny, and I never look at or retrieve about guys."

"Well, I like Lynn, and I might even like Lenny. How do you feel about that ?"

"I'd honey that, Nicole."

"And if I want you to be Lynn for me, at least some of the fourth dimension ?"

"I'd do that, if that's what you want."

"What about your little boyfriend flatness ?"

"I think he's getting a fiddling wear out of me."

"What if he isn't ?"

"I think I'd rather be with you anyhow."

"fountainhead, Lynn, let's see how you feel about that later tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the longest time. I wanted more of track, but I didn't want to rush thing and upset her and maybe crap her send me on my way. Nicole stroked my consistency, mostly back, weaponry, and ass, so I followed her track and did the Saame to her. After a yearn stretch of kissing and touching, Nicole stopped.

"Lynn, would you unbutton my blouse, delight ?"

I was more than happy to do so, though my hands were shaking as I began to undo the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her skirt, and she asked me to pull it on the loose and choose it off her. She sat there with only her bra on the upper half of her eubstance. I hardly even noticed as she took my blouse off me.

Nicole took one of my mitt and placed it on her white meat over her bra. I think my optic must deliver gotten very wide. She smiled, then leaned forward and kissed me as I held her pinhead. I wasn't sure where she was setting limit, but I couldn't help but rub her boob through her bra. Nicole moaned and continued to snog me.

My bra, of class, was filled with padding, not boobs, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the padding, it still sent a shudder of pleasure through my dead body. She had both custody on what would have been my boobs, if I had any, so I placed my early deal on her early breast.

I was a picayune concerned about pushing it too far, but Nicole seemed to get even more turned on. We continued like this for a patch before she asked me to unhook her bra. I had been fastening and unfastening the ones I wore for some time, but never messed with anyone else's bra. I reached behind her and fumbled a bit before getting it unhooked.

I rubbed her back where the bra had been, and Nicole moaned and squirmed, then shrugged, which let the bra pin forward. She had her coat of arms around me, as I had mine around her, so the bra didn't fall off. She reached behind me and unhooked my bra. We continued to osculate for a while before she leaned back to reserve our brassiere to strike off each of us.

My bra and padding fell to the trading floor, leaving my bare chest out there. I got my for the first time look at Nicole's boob - actually the first breasts I'd ever seen springy and in soul. I wanted to touch them but I was hesitant. I didn't want to strike too fast and spoil thing. Again Nicole put my hand on one of her knocker, then began to stroke my flat, boobless, chest.

Her dumbbell felt amazing, fond, piano, and just so marvelous. I began to fondle her titty and nipples as Nicole played with my chest. After a little spell, she stopped kissing me and guided my backtalk down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the boob right on her nipple.

Nicole leaned back, pulling me with her as I began to osculate and lick her bosom all over. Her tit got very hard and stood out farther than I realized they even could. Not only was I reveling in this, her breast seemed to racket in my attention. After a bit, she shifted my nous over to the former boob, and I began to contribute it the same attention that I'd been giving its partner.

I spent a long time cuddling and pleasing her breast, before Nicole clutched my head tightly to her as she moaned and writhed on the couch. As it settled back down again, she pulled me back up and kissed me before sitting us both up. I was afraid that she was indicating that we were done and was going to air me on my way. Instead Nicole stood and pulled me to my ft and led me by the bridge player into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, baby, unzip my skirt."

I unzipped her and she let the annulus slide down her body onto the floor. She stepped out of the dame, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet spot in the front man of them, as Nicole unzipped my skirt. My panties were having worry restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

"Lynn, I'll please you, but I want you to please me first. Okay ?"

"Anything you want, Nicole."

"start, take off my panties."

I moved down her body and Nicole lifted her rose hip off the bed. I slid her panty down and once they were top of her ass, she dropped her hips back to the bed and lifted her feet, letting me demand them completely off her. Nicole spread her legs and for the 1st time I got to see a woman's pussy. Nicole had shaved nearly of it, except for a narrow down strip just above her labia. Nicole gently pulled my top dog to her chthonian region, though I had no thought what I was supposed to do.

"O.K., babe. Kiss it, lick it, stick that clapper in me."

Nicole directed me as I ate her out, until she wrapped her stage around my read/write head, almost crushing me, while humping my mouth and moaning. My expression was wet with her juice as she released me, then pulled me back up to buss me. We kissed for a spell, until she rolled me over and got on top of me. She lifted up on my pelvis, so I raised them off the bed, and she pulled off my scanty.

I was still in full-of-the-moon makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the head of my bastard, which was as hard as I've ever seen it. smell, I'm no bully shakes in that section, but I've got about six inch, and it was in its to the full glory as Nicole slid back up my body.

I could experience my shit, sawing between her thighs, even rubbing across her pussy sass as Nicole writhed around on me. Finally, she lifted her hips, grabbed my prick and guided it into her sweet pussy. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was rich inside her. Once in, she paused a bit, getting us both used to the feel of me being in her.

"So, Lynn, do you call up you like this ?"

"I want to stay with you like this forever."

"I don't think you can keep it up that long, but let's enjoy what we can."

Nicole began moving her articulatio coxae taking my dick nearly out of her, then deeply in again. I was in promised land, and wished it could never end, even if I knew she was right on. I'd spent so a good deal clip jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her titty and fondled her ass. After a spell, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it mollycoddle, right inside me. take me up with it."

As I started to cum, I grabbed her ass and held her tight and as close to me as I could. I filled her with my cum until I had no more to give. I let go of her and just slumped back on the bed. Nicole leaned forward and kissed me sweetly.

"I know that isn't quite what your boyfriend would do to you, but I hope you enjoyed it anyhow, Lynn."

"That was wondrous. Better than anything I've ever done with Matt."

"We don't want you to miss out on anything though."

"What do you mean."

Nicole got off me, got up and walked over and opened a draftsman. She pulled out something that looked like a member, but with straps. She came back over to the bed and strapped it on herself, so it now appeared that she had a putz. She had me get on hands and knees, then got some lube from a nearby drawer, before lubing up the penis and my ass.

Nicole eased the matter into my ass, until I was well-to-do with it, then began to slowly fuck my ass with this strap-on. I wasn't sure I wanted her to do that, but at this breaker point, I wasn't going to argue with her. As she began fucking me, I began to get into it. For obvious reasonableness, she was able to keep going a lot longer than matte even could, and my turncock got hard again, and I came on the bed.

With that, she stopped and eased it out of my ass, then turned me over and kissed me some more. She kept the gimmick on her even through that. We kissed for a foresightful meter before she turned me on my side and spooned me, with her strap-on press up against my ass. We fell asleep that way and I had the most contented sleep that I've had in ages.

………………………………………………………………………………..

We woke up in the break of day, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me bang her pussy. We showered together, playing as we washed each other. I went down on her in the shower and she went down on me after.

"So, did you have any plans for tonight, Lynn ?"

"Nothing specific, but I'd love to spend it with you, if you're available."

"That sounds gravid. I've got some errands and affair to do this good afternoon, so you need to get your cute little ass home, and I'll see Lynn back here at seven."

"You'd rather be with me as Lynn than Lenny ?"

"For now. Do you have a problem with that ?"

"Not as long as I can spend my sentence with you."

"That's my girl. Now get dressed and scoot."

I put my dress back on. All I had was Lynn clothes, so I wore those and did my makeup before I left. I got back to my flat and sat on the sofa, just amazed at the last 24 hours. While I sat there, my earpiece rang - a yell from Matt.

"Hey, infant. Sorry I left you survive night, but Toni wanted to get out of there and you seemed all tied up with that brunette you were dancing with."

"That was Nicole. We were enjoying ourselves."

"I figured either she'd give you a raising house or you'd catch an Uber or something."

"Actually, she took me back to her lieu, and I spent the night there."

"So she was assuredness with Lynn and what Lynn was ?"

"Yeah, she was."

"So, Lynn, I was thinking that tonight…"

"Tonight, Nicole and I are going out again. Besides, you have Toni to go play with."

"You're raging than Toni."

"Maybe you should have thought of that before dumping me for her."

"Come on, girl. If it weren't for me, you'd have had no sex liveliness and no opportunity at that Nicole."

"But I have Nicole now, and I really like being with her."

"There are things I can do to you that she can't, unless she's like you."

"She's all missy, but she's got devices. I'm not missing out on anything, and I'm getting affair I could never get with you. I get to play with bosom, I get to jazz a pussy."

"Are you fucking dumping me, bitch ?"

"Matt, you've been a good protagonist, but I think we both need a change."

"Lynn, how long do you think that bitch will go before she dumps you ?"

"Don't know, but I'm going to run with this for as hanker as I can."

"I give it two hebdomad at the outside."

"well then, I'll take that two weeks. In the meantime, you have Toni or one of the other many women who fall all over themselves to be with you."

"Don't think I'll forget this."

"Just remember, if you out me as a hybridization dresser, you also out yourself as fucking a guy who cross dresses. Your footling girlfriends might not take that very well."

"You know that everything you've got with this Nicole, you owe to me."

"And you've sire payment for that. And if or when Nicole underprice me, if you aren't too big a bitch, you might even get more. In the lag, I hope you have a great evening."

So who was I ? Who did I want to be ? lustrelessness only wanted me as Lynn, and it was starting to reckon like Nicole did too. The difference was that I got more out of it with Nicole. It wasn't just me being fucked, I got a chance to get mine too. Fact is, given a choice, I'd rather be with Nicole or some other woman than to be with Matt.

I guessed I was epicene enough to get off on what I did with Matt, but why give up on char if I had any chance with them ? I was still sitting there in clothes as Lynn, when there was a whang on the room access. I was puzzled, because I wasn't expecting Nicole, lusterlessness, or anyone else for some time. I was a lilliputian leery of opening the door, when it was unlocked from outside.

I sat there shocked as my Sister Karen came in the apartment. She didn't speckle me immediately, but turned to close and lock the door. She saw me and her mouth hung afford and she seemed frozen in place until she began moving slowly toward me. Karen got over to me, reached out a hand and touched my face.

"Lenny ? What the fucking ?"

"Karen, I'm not quite certain how to explain this."

Karen sat down beside me on the couch, looking at me, then gingerly reaching out to touch what I was wearing.

"You're obviously in my clothes."

"Yes. It's kind of a recollective story."

"Are you wearing my panties and bras too ?"

"I am."

"I got a big place and was going to pick up the rest of my clothes, but if you've been wearing them, I don't think I want them anymore."

"I'm sorry. I'll pay you back, or buy you Sir Thomas More stuff."

"So is dressing like this what makes you happy ?"

"Not especially, but it makes the girl I spent the night with happy."

"A young lady ? A tangible young woman ? Not some in between or fake thing ?"

"Nicole is a real woman. For some understanding she gets off on being with me like this."

"Could be worse. You could be dressing like that and fucking guys."

I looked at my horseshoe. I couldn't look Karen in the facial expression. She understood immediately.

"screwing. You mean you did that too ?"

"As long as I have Nicole, I don't want or need any guys."

"But if she dumps you and you can't see another woman, you'll go back to fucking Guy ?"

"Karen, please."

"Lenny, it's your life. Fuck who you want. Just don't display up at home or my property dressed like that."

I was crying by this fourth dimension. Karen made me ashamed of what I'd done and what I'd become. At the same time, I needed love too, and if being Lynn was what kept Nicole then I was going to proceed to be Lynn. I wept on Karen's shoulder joint, and she took some pity on me and stroked my head and tried to soothe me. It took a while before I regained my composure.

"The real gripe is that you look better in those clothes than I did, Lenny."

"I hope you can infer and forgive me."

"I forgive you, and I guess I understand that you'll do whatever you have to do in order to get off."

"You were always popular with the guys. I could never get any of the girls to ease up me a minute look."

"So you dressed this way to get guys ?"

"I just dressed like this to get myself off, until a guy I knew saw me. He liked what he saw, and while I wasn't completely comfy, it was better than being alone."

"And this girl you're with now ?"

"Saw me, liked me, and figured out what I was. She liked char and men and seemed felicitous with me dressed like this."

"fountainhead, I guess I should be glad for you, even if I'm not thrilled about how you got there."

"I don't love how foresightful it'll last, but I'll do what I have to do to prevent it going."

"Should I still prognosticate you Lenny ?"

"When I'm like this, I'm go by Lynn."

"Well, Lynn, I wish you well with your lady friend. And I'm not going to wear any of the wearing apparel I left here, so they're all yours."

Karenic left, and I went in the bathroom to fix my makeup and then changed clothes. I'm not sure where the relationship with Nicole will take me, but I guess prison term will tell .