It started sort of strange. I am or at least was Len or Lenny - Elmore John Leonard to my mother - a guy in my early 20s, kind of forgetful and slender. I had a sister, Karen who was a few years honest-to-god than me. She'd had a nasty breakup with a fiancé, and stayed with me for a spell when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a squeamish minuscule brother, I let her accept the bed, while I slept on the sofa. She had a ton of dress and to a greater extent than filled my W.C., leaving short room for my apparel. Beyond that, we had to share one tiny can, in shimmy, since there was no way we were going to be in there at the same time - too minor and too weird.

Karenic stayed with me for about six months before getting her own place and moving out. Her seat was modest than mine, so while she took most of her stuff, she had more apparel than she had way for in the new place. She didn't want to donate them, so she asked if she could leave them at my place until she could open a bigger post. Again, being a nice brother, I let her do it.

Karenic left behind all mode of things, skirt, frock, blouses, bra, panties, shoes, makeup, and all that. After I while I got fascinated with it, which I supposition was my first mistake. I started by just touching some of the dress. I was a somewhat nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.

I started by just touching her clothes while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my head while doing myself. After a fourth dimension, that didn't turn me on the way it once did, so I even began putting on some of her dress. That seemed to be a cock-a-hoop turn-on and her clothes seemed to fit, since we were almost the Saame size.

As clock time went on, I'd garment up completely in Karen's wearing apparel for my self-abuse school term, and even left them on after I'd cum. I began to play with it all a minuscule bit and even began to use some of the war paint she'd left behind. I'd pad her bandeau with socks or whatever, put on scanty, a skirt, blouse, and shoes, then sweep my haircloth in a Thomas More womanly panache and learned how to do my makeup.

It all seemed innocent. I was in my space, by myself, using it all as part of self-abuse. inferno, I needed to get off too, and there were no fille willing to help me. Before long, I'd come home from work, dress up all girly, and prance around my apartment before getting myself off. I'd even wear one of Karen's old nightgown to bed afterward.

I had a few admirer who I'd hang out with occasionally. One of them, who I'd known since high schooling was lusterlessness. He was always the popular sort, never had any problem getting girlfriend, and often seemed to possess one or more than hanging off him. He'd pack 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 own, and we began talking. He started telling me about how he got some wench to let him finger her in world in a restaurant. He said they'd also gone to a moving-picture show house, sat way in backrest, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.

"Hey, Lenny, what's the far-out affair you've even done ?"

"Shit, Matt, I can't get girls to do ordinary bicycle shit with me, much less anything kinky."

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

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

"Seriously, Len. Do you just splay on her step-in to get turned on or do something more ?"

"Sometimes I'll go full drag, dress, shoe, makeup, and everything."

"Fuck, man, that I'd like to see."

"I don't know, dude. Nobody has ever seen me that way. I'd be freaked out to have someone see me."

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

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

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

That was Thursday, and it was already deep and I was too drunk and had to work on the next day. He asked if I'd cut back up for him the future night. I agreed and told him to come by after work on Friday, but to give me some time to get ready.

"Lenny, do you suppose you can be ready in an 60 minutes ?"

"I think so. I get home about six, so come by my place around seven."

…………………………………………………………………………

The next day I really had some regrets about agreeing to let him see me dressed up. I called him during lunch and tried to indorse out, but he said I'd promised and he expected me to keep my promise. I was on border all 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 slipstream, shaved my fount, legs, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the thought of having this guy see me in my sister's clothes. I dried my hair and styled it girlish, then put on panties, a bra, a squeamish skirt, and a blouse, then sat down to do war paint. By now I had it almost to a scientific discipline, putting on home, then some speech pattern, eyeliner, eye shadow, lip rouge, and of track I painted my toenails and fingernails.

I wore some low heels with exposed toes, to show off the toenail polish and looked at myself in the mirror. I knew I was a guy in retarding force, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the buzzer rang at seven o'clock. My articulatio genus were wobbly as I walked to the threshold. I looked through the peephole and indisputable sufficiency it was mat. I opened the threshold and let him in.

mat was gaping and staring as he walked in my spot. I closed and locked the room access and he turned me around then stepped back to hire a serious look at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me neural. He came back in front of me and grabbed me gently by the shoulders.

"Damn, that is hot, girl."

"I'm not a lady friend, I'm just dressed like one. I'm Lenny, you know that."

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

"okeh, Matt, you got to see me, now let me change back."

"clench on, Lynn, not so fast. Don't run off on me already. seed sit on the lounge with me."

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

"While you're like this, you're Lynn, and I like Lynn. Come on, delight sit on the lounge with me."

"This was a mistake. I shouldn't have done this. I want to change."

lustrelessness 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 joint and seemed to be getting way too much pleasance 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 aphrodisiacal girls I've seen in a while."

"You've got lots of missy - material girls, not fake one, like me."

"Don't tear yourself down. Most of those girls have nada on you."

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

"Let me bring you out to dinner, Lynn"

"Just let me exchange into some convention dress, Matt."

"No, babe, just like this."

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

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

"What if someone sees me - recognizes me ?"

"No one will distinguish 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 recognize, and besides I like a lilliputian bit of kinky sometimes."

"I don't know."

"semen on, Lynn. A nice dinner, and I'll kickshaw you the way a dame should be treated."

"That makes me feel really weird."

"And maybe a picayune turned on ?"

"I don't know if we should be doing this."

"I do, and we should."

With that, matte got up and imbibe me to my feet. He wrapped his weapons system around me and pulled me close. I think my eyes were the size of it of dish and my knees were getting faint as he leaned forward and kissed me on the impudence. He let go with one arm and walked me to the doorway. When we got there, he stopped and turned.

"Do you need a pocketbook, cay, and such ?"

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

"Grab one and your Francis Scott Key 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. lustrelessness went with me in the bedroom, and I went in the closet and found a purse that didn't flavour too bad with what I was wearing. I took my tonality and pocketbook and dropped them in the purse before turning to Matt.

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

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

Matt actually had money, which is yet another reason why most of the missy fell all over each early to get to him. We went downstairs to his mark new downcast BMW Z4 exchangeable and he opened the doorway 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 motor us to a very courteous restaurant.

He used gentleman 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 squeamish feeding bottle of wine-colored for us, and I really needed something to toast. I downed my first glass before he'd taken more than a couple sips of his wine. matte poured me another drinking glass, but I took it a trivial slower.

The server seemed very taken with me, and when he thought I didn't notice, tried looking down my blouse. various early men seemed to notice me, which made me squirm in my arse. One guy who works with mat stopped at the tabular array to talk with us. I'd met him several times before, but he clearly didn't greet me.

"Well, mat, who is this beautiful lady with you tonight ?"

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

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

"And I'm very pleased to play you, Lynn. mat is clearly a very prosperous man. But if you want a alteration of scenery, give me a call, I'd love to show you a sound time."

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

"Thanks, Oliver, but I'm not really looking for anyone else at the present."

"Well, Matt, if you get tired of Lynn here, experience free people to transmit her my way."

Joseph 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 shoes 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 adorable dinner and I continued to drink way more than than I should have. This entirely scene had blown my mind so lots 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 babble out to Matt. We finished dinner and I thought matte would claim me back to my place.

"Lynn, beloved, it's still early, why don't we go dancing ?"

"Are you sure about that ?"

"You're taking a walk on the raging side, just have a bit longer walk."

Matt wouldn't take ‘ no'for an resolution and drove us to the live club in town. This was the form of lieu that would never let the like of me inside. They must have had a hundred people lined up waiting to get in. Matt was obviously pretty well known, and he walked us up to the presence, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a crapulence and then matt wanted to dance with me. I felt unknown as shit, but it was a fast turn and I was already half plastered so I went out to trip the light fantastic with him. We danced several fast terpsichore, then a slow number came on. I thought we'd go sit down, but instead, mat pulled me close to him to dance.

He had one hand on my upper back, holding me tight, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could palpate that Matt had a hard-on as he did that. That scared me more than a fiddling, but I wasn't for certain what I could do. I felt helpless as we danced. When the number ended, Matt stopped, held me mean, and kissed me.

My articulatio genus got so rickety that if he hadn't been holding me smashed, I'd probably have slumped onto the story. He gave me a long candy kiss, and to my surprise, I began to kiss him back. I felt conflicted - I didn't feel like I should be doing this, not with a guy, but I seemed to be enjoying it. We kissed for a minute before he walked me back and we had another drink.

I'd been drinking pretty good before, but I didn't slow up down. I was half afraid of what was going to happen, and felt like I needed to be very drunk. We drank more and danced more, and the more we drank and danced, the More mat kept feeling me up and kissing me. My mind was blown - matte knew I was a guy dressed like a woman, yet he was acting like I was the real thing.

As I said, I'd been Matt's wingman more than a few clip, and had seen him this way with women many times before. I also knew that in virtually vitrine he ended up taking those women home and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don't know how foresightful we danced and drank, but by the meter matt was prepare to exit, I was really plastered.

I thought Matt was going to drive me back to my post, but instead he drove me to his flat. As I said, flatness had money, and he had a very nice two chamber apartment - nice furniture and all that. Part of me hoped that he was going to let me crash in the fifth wheel bedchamber. Another parting of me wanted anything but that.

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

"Lynn, honey, there's no hurriedness. Just relax and enjoy your walk on the wilderness side."

flatness got us each a beverage, like I needed any more alcohol, and sat me down on the lounge, sitting right-hand alongside me. lustrelessness put his arm around me and pulled me tight, then began to kiss me. He started just with the backtalk, then added in some tongue, while feeling up my ass and my false bosom. I seemed to be enjoying it, but felt that it was wrong.

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

"Sure we should. You seem to like it, and I told you I occasionally like kinky shit."

"I don't know if I'm ready to go any farther."

"Lynn, baby, I've shown you a sound time. I've made you sense skilful. You seem to be getting into this. Can't you help me feel upright too ?"

"What… What did you want 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 pants with his other deal. He pulled out his tool, which was already hard and standing straight up. He kissed me again, then gently pushed my straits down toward his prick. I got close and looked at it. It was foresightful 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 promontory of his dick between my lips.

mat moaned and leaned back, still keeping a hand on my capitulum. I let the head of his cock slip from between my lips, before taking it back and going just a little farther with it. I bobbed up and down on his putz, gradually taking it deeper and deeper into my mouth. I'd never had a dick in my oral cavity before and it felt foreign, but in another way, it felt very natural.

I slowly but steadily fucked his putz with my mouth and Matt seemed to like it. Some precum came from the tip, and it had a salty perceptiveness, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the al-Qaida of his dick as I sucked the rest of it. By now, flatness was moving his pelvic arch, almost fucking my mouth, as he held my heading tight.

Matt moaned loudly and got very rigid as his cock erupted in my mouth. He held my head with both men as he emptied his balls into my throat. I swallowed his cum and gasped for breath, though it took a couple of swallows to get it all down. It gradually eased and I cleaned his dick off as I pulled my head back from it.

Matt pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my mouth as we kissed, but that didn't seem to bother him. matte continued to kiss me and I didn't even realize it as he pulled my skirt up over my ass and began to caress my ass through my panties. He even snuck his manus into my panties and fondled my bare ass.

I don't know why I didn't notice, I don't know why I didn't stop him. Maybe I was enjoying it all too much, and maybe I was just too rummy. Before I even realized it, lusterlessness had removed my skirt and blouse and was carrying me into his chamber. I was so far gone at this stop I didn't know or care, or maybe it was what I really wanted.

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

"Do it, lusterlessness. Do it."

Matt set me down on his bed on my manpower and genu and pulled down my panty. My cock, which had been ignored for so prospicient sprang to care, but flatness was interested in other things. He took off his pant and shirt and got in bed behind me. He reached into a drawer in the board beside the bed and got a tube-shaped structure of lube.

lustrelessness rubbed lube over his motherfucker, then onto a finger's breadth which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able-bodied to proceed it pretty freely after a minute or two. He snuck a indorse finger in and began to finger bonk my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the back of my neck as he pulled his digit out of my ass.

I felt the head 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 mind get just inside me and I sighed and moved my ass back, getting more of him in me. It hurt a bit, but mat took it easy and slow at 1st, until I really started to get into it.

I soon felt his pelvis slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy piece of ass my ass, I'd have thought you were crazy and told you to leave me the know alone. Now matt was fucking me and I was in heaven. I felt his pecker sloping trough deep in me and fill me up. It turned me on in slipway I'd never have expected.

mat slid his dick in me so far, I could almost experience him jab my tum. I'd almost swear I saw my tum bulge as he got all the way in. In spite of whatever reservation I'd had, I was loving every moment of this, every stroke of his tool. I wanted his shaft in my ass, and when he came with a outburst in me, I came right onto his bed.

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

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

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

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

Essentially, Matt was spooning me as we lay there in his bed with his shaft slowly easing its way out of me. I moved my ass back, trying to keep as much of him in me for as recollective as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the next morning with flatness still spooning me and with his voiceless rooster pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's gruelling cock against my ass, I'd have leapt from bed and gotten out of the way 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 rachis of my neck as he eased around so his asshole 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 sides. It was a gentler nooky, instead of the pounding that we had at the end last Night, but I still loved it.

My dick got hard as I felt his fill me up. It was a slow leisurely nookie, 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 practically 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 night, and for this morn 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 break off 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 hawkshaw had slipped out of my ass and I'd rolled over look Matt. I kissed Matt, and he kissed me back and began stroking my eubstance. We spent a long metre smooching and touching each other before we got up and went to the exhibitioner together. Without my wearing apparel, 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 knee and sucked him off again. With my make-up off and hair's-breadth wet, I didn't look quite the Lapplander, but I dried my tomentum, styled it as best I could and got dressed in my wearing apparel from last night. I had a fiddling makeup in my pocketbook and could do lipstick, eyeliner and a little base, to make me more like Lynn.

The more I looked like Lynn, the more lusterlessness seemed to be affectionate. He fucked me once more before taking me place, and we made a date for that even.

When I got abode, I looked at myself in the mirror, then just slumped onto the redact and shake my head word. I could palpate 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 work it out along the way. For now, at least, I guess I was Lynn, until matte got tired of me or I got tired of it all. I venture Karen's supernumerary clothes were now Lynn's apparel till further notice.

Matt took me out again Sabbatum night, and took me back to his berth. We were not as tired or rummy and after I went down on him, he fucked me three time. I enjoyed it but as I drifted off to sleep, I was starting to find run afoul. Was this really how I wanted to live out my life ? And how longsighted was Matt likely to be interested in me ?

We fucked a couple more sentence the future morning time and I went home. I decided that Lynn would only be on Friday and Saturday nights. I was going to live and exercise as Lenny, the eternal sleep of the time. It was hard. We all want to be appreciated. We all want someone to think we are particular. 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. matt always found an attractive adult female to guide place. I was a little jealous - both of Matt and of the adult female. On rare occasions, I 'd be Lynn during the hebdomad, and flatness would number to my spot to get laid me. Usually Lynn was a weekend thing, but some weekends, flatness had other plans.

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

One Friday night, lusterlessness and I were at a club and I was being Lynn, though Matt seemed to be giving virtually of his tending to a very pretty blonde. I sat there feeling pretty neglected, when Nicole came up to utter to me. Nicole was a brunette, about my age, a bit taller, but with a very nice shape, b-cup titty, and a pretty face.

'' Well, love, your appointment seems to be ignoring you. ``

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

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

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

'' fountainhead, your guy appears to be about ready to ill-treat out with another cleaning woman. Would you let any interest in doing the same ? Or are you strictly into guy rope ? ``

'' You mean ... you 're interested in cleaning woman ? ``

'' I like charwoman. I like men. And sometimes I straddle the product line. ``

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

Nicole reached up, and stroked my face. I 'd shaved as cleanly as I could before going out with Matt, and my facial nerve hair's-breadth is not thick-skulled, but there was the slightest hint of very get down straw and I could tell by her expression that she felt it. Nicole leaned forward and kissed me.

'' Well, Lynn, something tells me that you straddle the short letter. ``

'' And you like that ? ``

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

'' I like adult female, I 'm just ... ''

Nicole took my paw and led me out onto the dance floor. I glanced back at flatness and he was so fixated on the blond that he never even noticed that I left. We did a twain of fast dances, and I really enjoyed dancing with Nicole. blaze, as Lenny, I had problem getting charwoman to even dance much with me.

A irksome telephone number came on and Nicole grabbed me and pulled me close. She put one hand in the center of my spinal column 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 acknowledge us or what we were doing.

At the end of the dance, Nicole gave me a kiss that almost buckled my knee joint. I could finger my dick getting harder and barely being restrained by my panties. My mind was blown. We stood there kissing for I'm not even sure how long. I'd never had a woman kiss me like that before, and I was in no hurry 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 same time, it didn't bother me that much. I wasn't sure that I wanted a prospicient term relationship with Matt, and he seemed to still be pretty much sleeping around. Besides, now Nicole seemed to be concerned in me, or at least I hoped she was.

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

"well, I guess I don't psyche, 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 swallow, danced a bit more then Nicole invited me back to her place. Nicole was an at bottom gross revenue rep for a tech companionship. She worked near where I did and made some decent money. I was still amazed that she had any interest in the ilk of me.

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

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

"I like girls, I just never had much luck before."

"So maybe you never met the right girlfriend before. As long as you're undefendable minded and whippy, I think we can experience lots of fun."

I felt a little uncertain. 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 girl who'd been out with a guy. Look, I'd never had any woman willing to give me the meter of day, much less get confidant with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

Matt had left me and gone off. I could either call an Uber or find out what Nicole had in head. Honestly it was probably better than what Matt had done, even though I seemed to enjoy fucking Matt. I sat for respective irregular, just pondering the possibilities. I looked at Nicole who sat there with a little enigmatical smile on her nerve, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walk on the wild side 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 club. She had a car nearby, nothing as expensive or flashy as matte's BMW, but a Nissan 370Z a duad of year old. It was certainly nicer than my eight yr old Civic. Nicole opened the car door for me, which surprised me a bit. Yes, flatness had been doing the Saami, but Nicole was a fair sex 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 immediate kiss.

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

"Best pass I've had in a farsighted time."

"Better than your picayune boyfriend ?"

"No question."

We were stopped, getting ready to drop dead the parking lot. I leaned over and gave Nicole a candy kiss. She smiled and stroked my head, before taking us out on the road. She drove us a few mil to her apartment. It was on the second flooring and we had to walk a flight of stairs, but we had our arms around each other, giggling and petting each other as we went.

Nicole had a nice trivial one bedroom place, clearly feminine, with a tone down floral sofa and chairs, along with some art prints on the rampart. The prints were largely of womanhood and men, along with a few where it wasn't quite clear if it was manlike or female. She walked me over and we sat on the sofa, and she put her arm around me.

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

"I really just started dressing up in my Sister's clothes as a turn-on. I told Matt one fourth dimension when I was drunkard 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 fourth dimension I go out this way is with him."

"But you were into guys ?"

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

"Have you been with any other guy cable than him ?"

"Never. most of the time, I'm Len or Lenny, and I never look at or cerebrate about guys."

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

"I'd making love that, Nicole."

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

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

"What about your niggling boyfriend Matt ?"

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

"What if he isn't ?"

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

"Well, 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 trend, but I didn't want to cannonball along things and upset her and maybe ready her send me on my way. Nicole stroked my eubstance, mostly back, implements of war, and ass, so I followed her lede and did the Sami to her. After a recollective stretching of kissing and touching, Nicole stopped.

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

I was more than felicitous 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 wench, and she asked me to pull it loose and withdraw it off her. She sat there with only her bra on the upper half of her body. I hardly even noticed as she took my blouse off me.

Nicole took one of my hands and placed it on her breast over her bra. I think my middle must give birth gotten very panoptic. She smiled, then leaned forward and kissed me as I held her knocker. I wasn't sure where she was setting limits, but I couldn't assistance but rub her titty through her bra. Nicole moaned and continued to kiss me.

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

I was a short 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 I 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 fall forward. She had her munition 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 buss for a while before she leaned back to countenance our bra to fall off each of us.

My bra and cushioning fell to the floor, leaving my bare chest out there. I got my first off feel at Nicole's breasts - actually the first breasts I'd ever seen live and in person. I wanted to touch them but I was hesitant. I didn't want to move too fast and spoil things. Again Nicole put my hand on one of her boobs, then began to stroke my flat, boobless, chest.

Her boobs felt nonplus, warm up, soft, and just so tremendous. I began to fondle her boobs and nipples as Nicole played with my chest. After a niggling piece, 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 boob right on her nipple.

Nicole leaned back, pulling me with her as I began to snog and lick her white meat all over. Her mammilla 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 attending. After a bit, she shifted my head over to the other dummy, and I began to give it the same attention that I'd been giving its partner.

I spent a long time fondling and pleasing her boob, before Nicole clutched my head 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 ft and led me by the deal 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 skirt slide down her physical structure onto the floor. She stepped out of the skirt, then kicked off her shoes. She now wore only panty, and I could see a decidedly wet spot in the front 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."

"number 1, take off my panties."

I moved down her body and Nicole lifted her hip joint off the bed. I slid her panties down and once they were clear of her ass, she dropped her hips back to the bed and lifted her feet, letting me take them completely off her. Nicole spread her legs and for the first time I got to see a cleaning woman's cunt. Nicole had shaved almost of it, except for a nail down striptease just above her labia. Nicole gently pulled my head to her nether part, though I had no thought what I was supposed to do.

"OK, baby. Kiss it, lick it, stick that tongue in me."

Nicole directed me as I ate her out, until she wrapped her legs around my head, almost crushing me, while humping my oral cavity and moaning. My face was wet with her juices as she released me, then pulled me back up to osculate 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 makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my pantie off, she kissed the head of my cocksucker, which was as gruelling as I've ever seen it. flavor, I'm no great shake in that department, but I've got about six inch, and it was in its full glory as Nicole slid back up my body.

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

"So, Lynn, do you recollect you like this ?"

"I want to stay on 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 hips 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 wing. I'd spent so lots time 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 while, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it pamper, rightfield 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 kick in. 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 beau would do to you, but I hope you enjoyed it anyhow, Lynn."

"That was wonderful. right than anything I've ever done with Matt."

"We don't want you to pretermit 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 penis, but with straps. 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 hand and knees, then got some lube from a nearby drawer, before lubing up the member and my ass.

Nicole eased the affair into my ass, until I was comfortable 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 distributor point, I wasn't going to argue with her. As she began fucking me, I began to get into it. For obvious understanding, she was capable to keep on going a lot longer than matte 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 contented sleep that I've had in ages.

………………………………………………………………………………..

We woke up in the sunup, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me fuck her kitty-cat. We showered together, playing as we washed each former. I went down on her in the shower and she went down on me after.

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

"Nothing particular, but I'd honey to pass it with you, if you're available."

"That sounds enceinte. I've got some errands and things to do this afternoon, so you need to get your cute little ass nursing 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 job with that ?"

"Not as long as I can spend my time 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 hours. While I sat there, my phone rang - a phone call from Matt.

"Hey, babe. Sorry I left you utmost nighttime, but Toni wanted to get out of there and you seemed all tied up with that brunet you were dancing with."

"That was Nicole. We were enjoying ourselves."

"I figured either she'd give you a lift family or you'd apprehension an Uber or something."

"Actually, she took me back to her seat, 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 hot 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 prospect at that Nicole."

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

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

"She's all female child, 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 recreate with pinhead, I get to roll in the hay a pussy."

"Are you fucking dumping me, bitch ?"

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

"Lynn, how long do you mean 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."

"Well then, I'll take that two workweek. 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 crown of thorns dressing table, you also out yourself as fucking a guy who cross dresses. Your petty girlfriends might not contract that very well."

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

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

So who was I ? Who did I want to be ? Matt only wanted me as Lynn, and it was starting to face like Nicole did too. The difference of opinion 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 bisexual person enough to get off on what I did with lusterlessness, but why give up on woman if I had any chance with them ? I was still sitting there in apparel as Lynn, when there was a knock on the door. I was puzzled, because I wasn't expecting Nicole, lusterlessness, or anyone else for some fourth dimension. I was a little leery of opening the door, when it was unlocked from outside.

I sat there shocked as my sister Karenic came in the apartment. She didn't speckle me immediately, but turned to close and lock the door. She saw me and her back talk hung unfold and she seemed rooted 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 screwing ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my pantie and bras too ?"

"I am."

"I got a liberal 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 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 girl ? A real girl ? Not some in between or cook thing ?"

"Nicole is a real woman. 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 feeling Karen in the face. 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 receive another woman, you'll go back to fucking guys ?"

"Karen, please."

"Lenny, it's your liveliness. roll in the hay who you want. Just don't show up at home or my berth dressed like that."

I was crying by this time. Karenic made me ashamed of what I'd done and what I'd become. At the same time, I needed get it on too, and if being Lynn was what kept Nicole then I was going to keep 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 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 translate 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 fille to pass on me a irregular look."

"So you dressed this way to get bozo ?"

"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 girl you're with now ?"

"Saw me, liked me, and figured out what I was. She liked charwoman and men and seemed well-chosen with me dressed like this."

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

"I don't get laid how long it'll last, but I'll do what I have to do to retain it going."

"Should I still call you Lenny ?"

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

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

Karen 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 time will tell .