It started variety of strange. I am or at least was Len or Lenny - Elmore John Leonard to my mother - a guy in my other 20s, kind of short and slender. I had a baby, Karen who was a few years previous 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 history back together.

It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a nice little sidekick, I let her stimulate the bed, while I slept on the lounge. She had a ton of clothes and more than filled my cupboard, leaving piddling elbow room for my clothes. Beyond that, we had to share one tiny lavatory, in shift key, since there was no way we were going to be in there at the same sentence - too small and too weird.

Karen stayed with me for about six calendar month before getting her own place and moving out. Her home was modest than mine, so while she took most of her material, she had more wearing apparel 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 position until she could afford a bigger seat. Again, being a nice brother, I let her do it.

Karen left behind all way of things, skirts, dresses, blouses, bandeau, panties, shoes, make-up, and all that. After I while I got fascinated with it, which I dead reckoning was my first error. I started by just touching some of the apparel. I was a reasonably nerdy guy who could never get anywhere with women, so even touching the apparel 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 time, that didn't turn me on the way it once did, so I even began putting on some of her apparel. That seemed to be a bigger turn-on and her apparel seemed to fit, since we were almost the Lapplander size.

As clip went on, I'd dress up completely in Karen's dress for my self-abuse school term, 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 physical composition she'd left behind. I'd pad her bras with air sock or whatever, put on panties, a skirt, blouse, and place, then sweep my hair in a more feminine style and learned how to do my makeup.

It all seemed innocent. I was in my home, by myself, using it all as part of self-stimulation. the pits, I needed to get off too, and there were no young woman bequeath to avail 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 friend who I'd hang out with occasionally. One of them, who I'd known since richly school was Matt. He was always the popular sort, never had any problem getting little girl, and often seemed to take in one or more hanging off him. He'd adopt me along as a wingman sometimes, though I never managed to get any girls out of it.

One Nox he and I were drinking, and I'd had to a greater extent than I should have, and we began talking. He started telling me about how he got some dame to let him finger her in populace in a restaurant. He said they'd also gone to a picture show theater, sat way in spine, 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 matter you've even done ?"

"diddly-squat, Matt, I can't get fille to do ordinary shit with me, much less anything kinky."

"Come on, guy, you must have done something just a lilliputian 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 broad drag, clothes, shoes, physical composition, and everything."

"piece of tail, 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 own individual see me."

"ejaculate 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 go away town."

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

That was Thursday, and it was already belated and I was too drunk and had to work the following 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 contribute me some clock time to get ready.

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

"I think so. I get dwelling house 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 tiffin and tried to back out, but he said I'd promised and he expected me to hold on my promise. I was on bound all good afternoon. I got dwelling house about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with perfume eubstance wash, shaved my facial expression, stage, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the idea of having this guy see me in my sister's clothes. I dried my hair and styled it girlish, then put on panty, a bra, a nice annulus, and a blouse, then sat down to do constitution. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye vestige, lipstick, and of trend I painted my toenails and fingernails.

I wore some low heels with open up toes, to testify off the toenail Polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly severalise when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o'clock. My human knee were wobbly as I walked to the door. I looked through the peephole and trusted enough it was Matt. I opened the doorway and let him in.

Matt was gaping and staring as he walked in my place. I closed and locked the threshold and he turned me around then stepped back to take a good tone at me. After looking at me a bit, he walked around behind me. He stroked my pilus 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 female child, I'm just dressed like one. I'm Lenny, you know that."

"The way you look, Lenny doesn't oeuvre. How about I call you Lynn ?"

"Okay, flatness, you got to see me, now let me alter back."

"storage area on, Lynn, not so fast. Don't run off on me already. Come sit on the lounge with me."

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

"While you're like this, you're Lynn, and I like Lynn. cum 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 slopped and walked me over to the sofa, 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."

"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 sexy missy I've seen in a while."

"You've got lots of young lady - real girls, not fake 1, like me."

"Don't buck yourself down. most of those miss 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 individual sees me - recognizes me ?"

"No one will agnise 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."

"cum on, Lynn. A courteous dinner party, and I'll treat you the way a lady should be treated."

"That makes me feel really weird."

"And maybe a fiddling 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 pes. He wrapped his weapon around me and pulled me closing curtain. I think my eyes were the size of dish aerial and my human knee were getting weak as he leaned forward and kissed me on the impudence. He let go with one arm and walked me to the threshold. When we got there, he stopped and turned.

"Do you need a purse, tonality, 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 wardrobe and found a purse that didn't look too bad with what I was wearing. I took my keys and pocketbook and dropped them in the pocketbook before turning to Matt.

"I'm really not sure we should be doing this, Matt."

"Everything is going to be just okay, Lynn."

Matt actually had money, which is yet another reason why about of the girl fell all over each early to get to him. We went downstairs to his brand new blue BMW Z4 convertible security and he opened the doorway of the car for me. I managed to sit down in a somewhat ladylike style - I don't think I showed too much. He got in and labour 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-colored for us, and I really needed something to drink. I downed my first spyglass before he'd taken more than a copulate sips of his vino. matte poured me another meth, but I took it a small slower.

The waiter seemed very taken with me, and when he thought I didn't posting, tried looking down my blouse. respective other men seemed to notice me, which made me wriggle 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, matte, who is this beautiful dame with you tonight ?"

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

"I'm so pleased to encounter you, Oliver."

"And I'm very pleased to converge you, Lynn. Matt is clearly a very lucky man. But if you want a change of scenery, break me a call, I'd love to demo you a adept time."

With that, Joseph 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."

"wellspring, Matt, if you get tired of Lynn here, feel free to charge her my way."

King Oliver bent down and kissed my impertinence before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot doll. 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 cover girl dinner party and I continued to drink way more than I should throw. This wholly tantrum had blown my nous so a good deal I didn't know what else to do. A few other men stopped to verbalise to us. They invariably seemed to pay inordinate care to me, when they stopped to mouth to lustrelessness. We finished dinner party and I thought Matt would use up 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 walkway on the wild position, just take a bit longer walk."

Matt wouldn't take ‘ no'for an result and force back us to the hottest club in town. This was the sort of topographic point that would never let the like of me inside. They must consume had a hundred people lined up waiting to get in. flatness 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 potable and then matte wanted to dance with me. I felt strange as diddlysquat, but it was a debauched number and I was already one-half plastered so I went out to dance with him. We danced respective fasting dances, then a slow issue came on. I thought we'd go sit down, but instead, Matt pulled me shut to him to dance.

He had one paw on my upper back, holding me wet, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could find that Matt had a hard-on as he did that. That scared me Thomas More than a little, but I wasn't sure what I could do. I felt incapacitated as we danced. When the number ended, Matt stopped, held me nasty, and kissed me.

My knees got so washy that if he hadn't been holding me tight, I'd probably have slumped onto the trading floor. He gave me a long candy kiss, and to my surprisal, I began to kiss him back. I felt infringe - 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 instant before he walked me back and we had another drink.

I'd been drinking pretty good before, but I didn't retard down. I was half afraid of what was going to bechance, and felt like I needed to be very drunk. We drank more and danced more, and the more we drank and danced, the to a greater extent Matt kept feeling me up and kissing me. My judgement was blown - Matt knew I was a guy dressed like a woman, yet he was acting like I was the really thing.

As I said, I'd been matte's wingman Thomas More than a few times, and had seen him this way with woman many clock time before. I also knew that in most pillowcase he ended up taking those cleaning lady base 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 flat. As I said, mat had money, and he had a very nice two bedchamber apartment - prissy 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 want 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 beverage, like I needed any more alcohol, and sat me down on the sofa, sitting right alongside me. matte put his arm around me and pulled me tight, then began to osculate me. He started just with the brim, then added in some natural language, while feeling up my ass and my impostor boobs. I seemed to be enjoying it, but felt that it was wrong.

"lusterlessness, we shouldn't be doing this."

"Sure we should. You seem to wish 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 secure time. I've made you finger practiced. You seem to be getting into this. Can't you help me experience well 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 bloomers with his other hand. He pulled out his prick, which was already severe and standing straight up. He kissed me again, then gently pushed my mind down toward his incision. I got near and looked at it. It was foresightful and difficult 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.

lusterlessness moaned and leaned back, still keeping a paw on my mind. I let the header of his putz 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 cryptic and deeper into my backtalk. I'd never had a gumshoe in my backtalk before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his cock with my backtalk and lustrelessness seemed to like it. Some precum came from the tip, and it had a salty sense of 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 radix of his hawkshaw as I sucked the rest of it. By now, Matt was moving his articulatio coxae, almost fucking my oral fissure, as he held my head tight.

mat moaned loudly and got very rigid as his cock erupted in my mouth. He held my head with both deal as he emptied his balls into my pharynx. I swallowed his cum and gasped for breath, though it took a couple of swallow to get it all down. It gradually eased and I cleaned his prick 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 rile him. flatness continued to buss me and I didn't even take in it as he pulled my dame up over my ass and began to caress my ass through my panties. He even snuck his hand into my panty and fondled my bare ass.

I don't know why I didn't bill, 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 bird and blouse and was carrying me into his chamber. I was so far gone at this point I didn't know or worry, or maybe it was what I really wanted.

"Lynn, baby. You are terrific and beautiful, and I love what we've done, but I need to fuck you."

"Do it, matte. Do it."

Matt set me down on his bed on my bridge player and knees and pulled down my scanty. My cock, which had been ignored for so long sprang to aid, but lusterlessness was matter to in other things. 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 thermionic valve of lube.

Matt rubbed lubricating substance 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 hour or two. He snuck a second finger in and began to feel know my ass, and in malice of myself, I began to fuck him back. matte leaned down and kissed the back of my neck opening as he pulled his fingers out of my ass.

I felt the head word of his cock at my asshole 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 principal get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but Matt took it easy 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 softheaded and told you to pull up stakes me the fuck alone. Now mat was fucking me and I was in heaven. I felt his turncock chute deep in me and fill me up. It turned me on in ways I'd never have expected.

Matt slid his cock in me so far, I could almost feel him jab my stomach. I'd almost swear I saw my breadbasket bulge as he got all the way in. In spite of whatever reservations I'd had, I was loving every second of this, every throw of his cock. I wanted his dick in my ass, and when he came with a outpouring in me, I came right onto his bed.

Matt collapsed onto me and I collapsed and we rolled onto our side of meat, with his son of a bitch still inside me. I was on a intimate high and wanted aught more than to go on feeling his prick in my ass. His dick was getting balmy, but I wanted to keep him in me as long as I could. As we came off our high, lusterlessness began to stroke my shoulders and kiss the back and side of my neck.

"Lynn, infant, you are beautiful, sexy, and wonderful, and I just wish I could detain inside you forever."

"I wish you could outride 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 turncock slowly easing its way out of me. I moved my ass back, trying to sustain as practically of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the future dawn with lusterlessness still spooning me and with his hard cock pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's hard dick against my ass, I'd have leapt from bed and gotten out of the room as fast as I could. Instead, I moaned and moved my ass around against his prick.

Matt woke up and began stroking me and kissing the spinal column of my neck as he eased around so his prick was up against my arsehole. I could feel it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our position. It was a gentler screwing, instead of the buffeting that we had at the end live on dark, but I still loved it.

My dick got laborious as I felt his filling me up. It was a boring leisurely fucking, almost loving, and I reached behind me to stroke flatness's body as he fucked me. He pressed tight against me as he came deep in my ass. I couldn't believe how practically I enjoyed having this guy fuck me, but I knew I wanted it to keep as long as he wanted me.

"Lynn, baby, thank you for last night, and for this morning too."

"I hope we'll have Sir Thomas More than just last dark and this morning."

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

"I want it. I want your cock in my ass, in my mouth, 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 dick had slipped out of my ass and I'd rolled over facing mat. I kissed matte, and he kissed me back and began stroking my body. We spent a foresighted clip fondling and touching each other before we got up and went to the exhibitor together. Without my clothes, my bra, my panty, 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 composition off and haircloth wet, I didn't look quite the same, but I dried my hairsbreadth, styled it as topper I could and got dressed in my wearing apparel from last nighttime. I had a little war paint in my pocketbook and could do lipstick, eyeliner and a trivial stand, to make me more like Lynn.

The more I looked like Lynn, the more Matt seemed to be affectionate. He fucked me once more before taking me home, and we made a engagement for that eve.

When I got abode, I looked at myself in the mirror, then just slumped onto the couch and shake off my oral sex. I could feel lustrelessness'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 do work 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 suppose Karen's extra clothes were now Lynn's apparel till further notice.

flatness took me out again Saturday nighttime, and took me back to his place. We were not as exhaust or drunk and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to catch some Z's, I was starting to feel conflicted. Was this really how I wanted to hold up out my life ? And how long was Matt likely to be interested in me ?

We fucked a couple more metre the future dawning and I went dwelling. I decided that Lynn would only be on Friday and Sabbatum Nox. I was going to hold out and turn as Lenny, the sleep of the time. It was hard. We all want to be appreciated. We all want someone to opine we are especial. Lenny is n't especial to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as Matt 's wingman. matte always found an attractive woman to take home. I was a fiddling jealous - both of matt and of the woman. On rare occasion, I 'd be Lynn during the hebdomad, and flatness would come to my place to sleep together me. Usually Lynn was a weekend thing, but some weekends, Matt had other plans.

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

One Friday night, Matt and I were at a nine and I was being Lynn, though mat seemed to be giving about of his attention to a very fairly blonde. I sat there feeling pretty neglected, when Nicole came up to talk to me. Nicole was a brunet, about my age, a bit taller, but with a very nice condition, b-cup pinhead, and a pretty face.

'' fountainhead, honey, your date seems to be ignoring you. ``

'' I guess I 'm old intelligence. ``

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

'' Hi, Nicole. I 'm Lynn. And Matt and I have kind of an unusual human relationship. ``

'' Well, your guy appears to be about ready to abuse out with another woman. Would you have any interest in doing the same ? Or are you strictly into guys ? ``

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

'' I like women. I like men. And sometimes I straddle the line. ``

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

Nicole reached up, and stroked my aspect. I 'd shaved as cleanly as I could before going out with lusterlessness, and my nervus facialis hair is not blockheaded, but there was the slightest tincture of very light chaff and I could differentiate by her formula that she felt it. Nicole leaned forward and kissed me.

'' wellspring, Lynn, something tells 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 women. ``

'' I like charwoman, I 'm just ... ''

Nicole took my hand and led me out onto the dance floor. I glanced back at Matt and he was so fixated on the blond that he never even noticed that I left. We did a match of degenerate dances, and I really enjoyed dancing with Nicole. Hell, as Lenny, I had trouble getting cleaning woman to even dance a great deal with me.

A slow telephone number came on and Nicole grabbed me and pulled me finish. She put one hand in the centre of my back and the former one down over my ass. I giggled and squirmed as she caressed my ass through the saltation. 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 genu. I could feel my cock getting laborious and barely being restrained by my panty. My mind was blown. We stood there kissing for I'm not even sure how long. I'd never had a char kiss me like that before, and I was in no hurry for it to end.

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

"well, Lynn honey, it looks like you lost your guy."

"wellspring, I guess I don't judgement, at least 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 drink, danced a bit more then Nicole invited me back to her home. Nicole was an interior sale rep for a tech company. She worked near where I did and made some in good order money. I was still amazed that she had any interest in the the like of me.

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

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

"I like young lady, I just never had much luck before."

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

I felt a little changeable. Nicole was pretty and she seemed will. I just didn't understand why she'd have any interest in me - not after knowing that I was a guy dressed as a lady friend who'd been out with a guy. Look, I'd never had any char willing to give me the sentence of day, much less get confidant with me. Nicole figured out what I really was and still seemed interest. Now that was kinky.

matte had left me and gone off. I could either anticipate an Uber or notice out what Nicole had in mind. Honestly it was probably expert than what matte had done, even though I seemed to enjoy fucking flatness. I sat for various instant, just pondering the possibilities. I looked at Nicole who sat there with a niggling puzzling smile on her face, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walking on the wild side anyhow, why not walk a piddling farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the clubhouse. She had a car nearby, zilch as expensive or flashy as flatness's BMW, but a Nissan 370Z a mates of years 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 womanhood 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 threshold, Nicole leaned over and kissed me. She came around, sat down in the driver's arse and started the car. Before she put it in geartrain, she smiled at me again and gave me a quick kiss.

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

"best offer I've had in a farseeing time."

"better than your little beau ?"

"No question."

We were stopped, getting ready to snuff it 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 stat mi to her flat. It was on the indorse storey and we had to walk a flight of stairs of stairs, but we had our arms around each early, giggling and petting each other as we went.

Nicole had a nice little one bedroom station, clearly feminine, with a muted floral sofa and chair, along with some art mark on the wall. The prints were largely of womanhood and men, along with a few where it wasn't quite all the way if it was Male or female. She walked me over and we sat on the lounge, 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 Matt one prison term when I was inebriate and he wanted me to dress up for him."

"Obviously, you did."

"He liked the way I looked and wanted to take 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 plate and fucked me."

"Have you been with any early guys than him ?"

"Never. to the highest degree of the time, I'm Len or Lenny, and I never look at or think about guys."

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

"I'd love that, Nicole."

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

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

"What about your short boyfriend matte ?"

"I think he's getting a little tired of me."

"What if he isn't ?"

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

"wellspring, 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 Thomas More of course, but I didn't want to cannonball along things and upset her and maybe make her send me on my way. Nicole stroked my consistence, mostly back, arms, and ass, so I followed her spark advance and did the Lapplander to her. After a prospicient stretch of kissing and touching, Nicole stopped.

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

I was more than well-chosen to do so, though my helping hand were shaking as I began to unmake the clit. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her chick, and she asked me to pull up it slack and bring it off her. She sat there with only her bra on the upper half of her dead body. I hardly even noticed as she took my blouse off me.

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

My bra, of course, was filled with padding, not drop the ball, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the cushioning, it still sent a shiver of pleasure through my soundbox. She had both hired hand on what would have been my boobs, if I had any, so I placed my other handwriting on her other breast.

I was a little concerned about pushing it too far, but Nicole seemed to get even more turned on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the ones I wore for some meter, 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 declension forward. She had her 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 kiss for a while before she leaned back to admit our bandeau to strike off each of us.

My bra and padding fell to the floor, leaving my bare chest out there. I got my first-class honours degree flavour at Nicole's chest - actually the number one boob I'd ever seen live and in somebody. I wanted to rival them but I was hesitant. I didn't want to move too fast and bollocks up thing. Again Nicole put my hand on one of her booby, then began to stroke my flat, boobless, chest.

Her boobs felt amazing, ardent, soft, and just so wonderful. I began to caress her dummy and nipple as Nicole played with my chest. After a picayune spell, she stopped kissing me and guided my mouth down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the bosom right on her nipple.

Nicole leaned back, pulling me with her as I began to buss and lick her breast all over. Her nipple got very hard and stood out farther than I realized they even could. Not only was I reveling in this, her breast seemed to jollify in my attention. After a bit, she shifted my head over to the other boob, and I began to give it the like aid that I'd been giving its partner.

I spent a long prison term kissing and pleasing her breasts, before Nicole clutched my head teacher tightly to her as she moaned and writhed on the sofa. 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 mail me on my way. Instead Nicole stood and pulled me to my understructure and led me by the hired hand 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 dame slide down her body onto the base. She stepped out of the doll, then kicked off her place. She now wore only panties, and I could see a decidedly wet patch in the front line of them, as Nicole unzipped my skirt. My panties were having trouble 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."

"First, subscribe to off my panties."

I moved down her body and Nicole lifted her hip off the bed. I slid her pantie down and once they were clear of her ass, she dropped her hips back to the bed and lifted her animal foot, letting me require them completely off her. Nicole spread her legs and for the first time I got to see a cleaning woman's pussycat. Nicole had shaved near of it, except for a narrow cartoon strip just above her labia. Nicole gently pulled my head to her nether regions, though I had no musical theme what I was supposed to do.

"Okay, baby. Kiss it, lick it, stick that glossa in me."

Nicole directed me as I ate her out, until she wrapped her pegleg around my top dog, almost crushing me, while humping my mouth and moaning. My facial expression was wet with her succus as she released me, then pulled me back up to kiss me. We kissed for a while, until she rolled me over and got on top of me. She lifted up on my hips, so I raised them off the bed, and she pulled off my panties.

I was still in full make-up as Lynn, even if I basically looked like Lenny from the neck opening down. As she pulled my panties off, she kissed the pass of my prick, which was as hard as I've ever seen it. facial expression, I'm no nifty waggle in that section, but I've got about six inch, and it was in its wide glory as Nicole slid back up my body.

I could feel my prick, sawing between her thighs, even rubbing across her kitty back talk as Nicole writhed around on me. Finally, she lifted her hips, grabbed my dick and guided it into her perfumed cunt. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was deep inside her. Once in, she paused a bit, getting us both used to the smell of me being in her.

"So, Lynn, do you intend 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 bask what we can."

Nicole began moving her hip taking my dick nearly out of her, then deeply in again. I was in heaven, and wished it could never end, even if I knew she was mighty. I'd spent so a lot time jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her dope and fondled her ass. After a while, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it cosset, right inside me. Fill 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 wonderful. effective 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 drawer. She pulled out something that looked like a phallus, but with strap. She came back over to the bed and strapped it on herself, so it now appeared that she had a dick. She had me get on hands and knees, then got some lube from a nearby drawer, before lubing up the phallus and my ass.

Nicole eased the affair into my ass, until I was well-off with it, then began to slowly do it my ass with this strap-on. I wasn't sure I wanted her to do that, but at this point, I wasn't going to argue with her. As she began fucking me, I began to get into it. For obvious reasons, she was able to keep going a lot foresighted than flatness even could, and my cock 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 device on her even through that. We kissed for a long time before she turned me on my side and spooned me, with her strap-on pressing up against my ass. We fell asleep that way and I had the most content sleep that I've had in ages.

………………………………………………………………………………..

We woke up in the break of the day, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me fuck 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 architectural plan for tonight, Lynn ?"

"cypher specific, but I'd love to pass it with you, if you're available."

"That sounds big. I've got some errands and things to do this afternoon, so you need to get your precious minuscule ass rest 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 meter with you."

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

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

"Hey, babe. Sorry I left you last 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 lift place or you'd gimmick an Uber or something."

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

"So she was cool 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 spicy 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 life and no chance 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 young woman, but she's got devices. I'm not missing out on anything, and I'm getting things I could never get with you. I get to play with boobs, I get to fuck a pussy."

"Are you fucking dumping me, backbite ?"

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

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

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

"I give it two weeks at the outside."

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

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

"Just remember, if you out me as a crisscross chest of drawers, you also out yourself as fucking a guy who cross dresses. Your little girlfriends might not take that very well."

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

"And you've gotten payment for that. And if or when Nicole underprice me, if you aren't too big a gripe, you might even get more. In the meantime, 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 depend 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 opportunity to get mine too. Fact is, given a pick, I'd rather be with Nicole or some other woman than to be with Matt.

I guessed I was bisexual enough to get off on what I did with lustrelessness, but why give up on women if I had any chance with them ? I was still sitting there in clothes as Lynn, when there was a belt on the door. I was puzzled, because I wasn't expecting Nicole, Matt, or anyone else for some prison term. I was a picayune 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 spot me immediately, but turned to close and lock up the door. She saw me and her mouth hung open and she seemed wintry in place until she began moving slowly toward me. Karen got over to me, reached out a paw and touched my face.

"Lenny ? What the fuck ?"

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

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

"You're obviously in my clothes."

"Yes. It's variety of a foresightful story."

"Are you wearing my panties and bras too ?"

"I am."

"I got a swelled place and was going to blame 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 Nox with happy."

"A daughter ? A really girlfriend ? Not some in between or fake thing ?"

"Nicole is a existent cleaning lady. For some reason 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 shoes. I couldn't look Karenic in the brass. She understood immediately.

"piece of ass. 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 find another woman, you'll go back to fucking guys ?"

"Karen, please."

"Lenny, it's your spirit. shtup who you want. Just don't show up at place or my place dressed like that."

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

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

"I hope you can understand and forgive me."

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

"You were always popular with the guys. I could never get any of the daughter to give me a second look."

"So you dressed this way to get guy rope ?"

"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 comfortable, it was better than being alone."

"And this girlfriend you're with now ?"

"Saw me, liked me, and figured out what I was. She liked fair sex and men and seemed happy with me dressed like this."

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

"I don't sleep together how long it'll survive, but I'll do what I have to do to keep it going."

"Should I still squall 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 get into any of the clothes I left here, so they're all yours."

Karen left, and I went in the lav to fix my make-up and then changed clothes. I'm not sure where the relationship with Nicole will take me, but I guess time will tell .