It started kind of strange. I am or at to the lowest degree was Len or Lenny - Dutch Leonard to my female parent - a guy in my former 20s, kind of short circuit and slender. I had a sister, Karenic who was a few long time erstwhile 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 lifetime back together.

It was a bit inconvenient, since I just had a one sleeping accommodation station, and not all that big. Being a nice little brother, I let her have the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving slight way for my clothes. Beyond that, we had to parcel one tiny bathroom, in shifts, since there was no way we were going to be in there at the Lapplander time - too small and too weird.

Karen stayed with me for about six month before getting her own post and moving out. Her home was smaller than mine, so while she took to the highest degree of her stuff, she had more clothes than she had way for in the new stead. She didn't want to donate them, so she asked if she could leave them at my place until she could afford a bigger place. Again, being a nice chum, I let her do it.

Karen left behind all manner of things, skirts, dresses, blouses, bra, pantie, shoes, makeup, and all that. After I while I got fascinated with it, which I speculation was my first error. I started by just touching some of the clothes. I was a jolly nerdy guy who could never get anywhere with charwoman, so even touching the clothes was a turn-on.

I started by just touching her dress while touching myself, then jerking off until I came. I progressed to smelling the dress 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 dress. That seemed to be a grownup turn-on and her clothes seemed to fit, since we were almost the Saami size.

As time went on, I'd line up up completely in Karen's clothes for my self-abuse sessions, and even left them on after I'd cum. I began to play with it all a little bit and even began to use some of the make-up she'd left behind. I'd pad her brassiere with drogue or whatever, put on panties, a bird, blouse, and shoes, then brush my hair in a more feminine style and learned how to do my makeup.

It all seemed destitute. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no young woman bequeath to help me. Before farsighted, I'd come dwelling from work, coiffe up all girly, and prance around my flat before getting myself off. I'd even wear one of Karen's old night-robe to bed afterward.

I had a few Friend who I'd hang out with occasionally. One of them, who I'd known since high schoolhouse was Matt. He was always the popular form, never had any problem getting girls, and often seemed to take in one or more hanging off him. He'd film me along as a wingman sometimes, though I never managed to get any girls out of it.

One Night he and I were drinking, and I'd had more than I should have, and we began talking. He started telling me about how he got some skirt to let him thumb her in public in a eatery. He said they'd also gone to a movie dramatic art, sat way in back, and she hiked up her dame, sat on his lap, and fucked him in the field during the movie.

"Hey, Lenny, what's the kinkiest thing you've even done ?"

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

"semen on, guy, you must hold done something just a picayune bit out there."

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

"Seriously, Len. Do you just slide on her pantie to get turned on or do something more ?"

"Sometimes I'll go full puff, wearing apparel, shoes, makeup, and everything."

"ass, 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 consume someone see me."

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

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

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

That was Thursday, and it was already late and I was too imbibe and had to exploit the next day. He asked if I'd dress up for him the next night. I agreed and told him to come by after study on Friday, but to feed me some clip to get ready.

"Lenny, do you think you can be gear up in an hour ?"

"I think so. I get menage about six, so come by my station 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 hold back my promise. I was on sharpness all afternoon. I got home plate about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with scented body laundry, shaved my font, 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 babe's clothes. I dried my hair and styled it girlish, then put on panties, a bra, a nice skirt, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on base, then some accents, eyeliner, eye apparition, lipstick, and of course of study I painted my toenails and fingernails.

I wore some low cad with open toes, to bear witness 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 neural when the doorbell rang at seven o'clock. My stifle were wobbly as I walked to the room access. I looked through the peephole and for certain adequate it was flatness. I opened the door and let him in.

mat was gaping and staring as he walked in my place. I closed and locked the room access and he turned me around then stepped back to take a good facial expression at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me nervous. He came back in forepart of me and grabbed me gently by the shoulders.

"Damn, that is hot, girl."

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

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

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

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

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

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

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

matte put and arm around me tight and walked me over to the couch, pulling me down beside him there. He had his arm around my shoulder and seemed to be getting way too often pleasure out of this.

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

"Matt, this tone really weird."

"Not weird, Lynn, just a trivial kinky, baby."

"No one has ever seen me like this before. I feel uncomfortable."

"You shouldn't be uncomfortable. You look howling, one of the sexiest daughter I've seen in a while."

"You've got sight of girls - genuine girls, not fake single, like me."

"Don't shoot yourself down. Most of those girlfriend have nix on you."

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

"Let me take you out to dinner, Lynn"

"Just let me commute into some convention clothes, Matt."

"No, babe, just like this."

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

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

"What if someone sees me - recognizes me ?"

"No one will recognize you as that nerdy guy."

"Doesn't it bother you to be out in public with a guy in drag ?"

"No one but you and I will know, and besides I like a little bit of kinky sometimes."

"I don't know."

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

"That makes me experience really weird."

"And maybe a little turned on ?"

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

"I do, and we should."

With that, lusterlessness got up and pull out me to my feet. He wrapped his arms around me and pulled me nigh. I think my eyes were the size of saucer and my knees were getting weak as he leaned forward and kissed me on the impertinence. He let go with one arm and walked me to the door. When we got there, he stopped and turned.

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

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

"snatch 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 cupboard and found a purse that didn't facial expression too bad with what I was wearing. I took my cay and wallet and dropped them in the handbag before turning to Matt.

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

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

Matt actually had money, which is yet another ground why virtually of the young lady fell all over each other to get to him. We went downstairs to his brand name new blue BMW Z4 transmutable and he opened the door of the car for me. I managed to sit down in a somewhat ladylike way - I don't think I showed too very much. He got in and drove us to a very nice restaurant.

He used valet de chambre parking and walked me in, holding the door for me. I still felt Wyrd as diddlyshit, but just tried to brush aside how I looked and bask myself. mat ordered a nice bottle of vino for us, and I really needed something to drink. I downed my first glass before he'd taken more than a couple sips of his wine-colored. Matt poured me another drinking glass, but I took it a lilliputian slower.

The waiter seemed very taken with me, and when he thought I didn't observance, tried looking down my blouse. Several early men seemed to comment me, which made me squirm in my seat. One guy who works with matte stopped at the tabular array to utter with us. I'd met him several fourth dimension before, but he clearly didn't acknowledge me.

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

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

"I'm so proud of to meet you, Oliver."

"And I'm very pleased to run into you, Lynn. Matt is clearly a very golden man. But if you want a change of scenery, leave me a vociferation, I'd love to show you a good time."

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

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

"Well, Matt, if you get tired of Lynn here, feel absolve to send her my way."

Oliver bent down and kissed my brass before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot chick. Half the men in this post would dump their date for a prospect to take you home."

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

We had a endearing dinner and I continued to drink way more than I should have. This altogether scenery had blown my idea so much I didn't know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to spill the beans to Matt. We finished dinner and I thought mat would take me back to my place.

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

"Are you sure about that ?"

"You're taking a walk on the savage side, just engage a bit longer walk."

Matt wouldn't take ‘ no'for an result and labour us to the spicy social club in town. This was the sort of place that would never let the likes of me inside. They must have had a hundred the great unwashed lined up waiting to get in. lusterlessness 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 beverage and then Matt wanted to dance with me. I felt strange as shite, but it was a loyal number and I was already half plastered so I went out to trip the light fantastic toe with him. We danced various fast dances, then a slow number came on. I thought we'd go sit down, but instead, matt pulled me close to him to dance.

He had one deal on my speed back, holding me tight, as his other hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that mat had a hard-on as he did that. That scared me more than a picayune, but I wasn't certainly what I could do. I felt lost as we danced. When the number ended, Matt stopped, held me tight, and kissed me.

My knee got so weak that if he hadn't been holding me tight, I'd probably have slumped onto the trading floor. He gave me a longsighted osculation, and to my surprisal, I began to osculate 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 bit before he walked me back and we had another deglutition.

I'd been drinking pretty right before, but I didn't decelerate down. I was one-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 to a greater extent Matt kept feeling me up and kissing me. My mind was blown - Matt knew I was a guy dressed like a woman, yet he was acting like I was the real thing.

As I said, I'd been matte's wingman more than a few times, and had seen him this way with cleaning lady many times before. I also knew that in nigh typesetter's case 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 recollective we danced and drank, but by the time lusterlessness was prepare to provide, 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, matte had money, and he had a very nice two bedroom apartment - dainty furniture and all that. persona of me hoped that he was going to let me go down in the scanty bedroom. Another voice of me wanted anything but that.

"Matt, I really need to get base and change."

"Lynn, honey, there's no hurry. Just relax and love your walkway on the angry side."

mat got us each a drink, like I needed any more intoxicant, and sat me down on the couch, sitting right alongside me. Matt put his arm around me and pulled me tight, then began to kiss me. He started just with the mouth, then added in some glossa, while feeling up my ass and my fake boobs. I seemed to be enjoying it, but felt that it was wrong.

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

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

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

"Lynn, baby, I've shown you a good time. I've made you feel good. You seem to be getting into this. Can't you serve me palpate good too ?"

"What… What did you need me to do ?"

"If cypher else, can you at to the lowest degree go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

matte kissed me and stroked my ass as he unzipped his pants with his other hand. He pulled out his cock, which was already toilsome and standing straight up. He kissed me again, then gently pushed my head down toward his prick. I got end and looked at it. It was long and punishing and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the read/write head of his pecker between my lips.

Matt moaned and leaned back, still keeping a hand on my question. I let the foreland of his cock faux pas from between my lips, before taking it back and going just a niggling farther with it. I bobbed up and down on his prick, gradually taking it thick and deeper into my mouth. I'd never had a shaft in my mouth before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his peter with my oral cavity and matte seemed to like it. Some precum came from the tip, and it had a salty gustatory modality, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the bag of his dick as I sucked the rest of it. By now, Matt was moving his articulatio coxae, almost fucking my mouth, as he held my top dog tight.

lusterlessness moaned loudly and got very rigid as his stopcock erupted in my mouth. He held my headspring with both hands as he emptied his orb into my throat. I swallowed his cum and gasped for breathing spell, though it took a span of deglutition to get it all down. It gradually eased and I cleaned his gumshoe off as I pulled my forefront back from it.

lustrelessness pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my sass as we kissed, but that didn't seem to bother him. Matt continued to snog 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 pantie. He even snuck his hand into my panties and fondled my bare ass.

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

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

"Do it, Matt. Do it."

matte set me down on his bed on my helping hand and stifle and pulled down my panty. My stopcock, which had been ignored for so long sprang to care, but matte was interested in other things. He took off his trouser and shirt and got in bed behind me. He reached into a drawer in the tabular array beside the bed and got a tube of lube.

lustrelessness rubbed lube over his prick, then onto a finger which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able to motivate it pretty freely after a minute or two. He snuck a second finger in and began to feel fuck my ass, and in spite of myself, I began to get it on him back. matt leaned down and kissed the backbone of my neck as he pulled his fingers out of my ass.

I felt the head of his cock at my bastard and tensed for just a irregular before relaxing. At this gunpoint, I think I wanted him as much as he wanted me. I felt the oral sex get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but matte took it easily and decelerate at initiative, 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 gaga and told you to leave me the have intercourse alone. Now matt was fucking me and I was in paradise. I felt his cock slide trench in me and fill me up. It turned me on in path I'd never have expected.

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

matt collapsed onto me and I collapsed and we rolled onto our position, with his prick still inside me. I was on a sexual high and wanted zero more than to keep feeling his pecker in my ass. His dick was getting softer, but I wanted to stay fresh him in me as long as I could. As we came off our high, Matt began to stroke my shoulders and kiss the spinal column and side of my neck.

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

"I wish you could remain 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 cock slowly easing its way out of me. I moved my ass back, trying to keep back as much of him in me for as longsighted as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the next morning with mat still spooning me and with his arduous shaft pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's strong 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 back of my neck as he eased around so his asshole was up against my arse. I could find it and wanted it back inside me. I reached around, grabbed his putz and guided it into my ass, as we lay on our sides. It was a gentler piece of tail, instead of the buffeting that we had at the end finis night, but I still loved it.

My dick got hard as I felt his woof me up. It was a slow leisurely screw, 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 much I enjoyed having this guy fuck me, but I knew I wanted it to continue as long as he wanted me.

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

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

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

"I want it. I want your stopcock in my ass, in my lip, 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 home of Lenny. I need to be Lenny at work."

By then, matte's dick had slipped out of my ass and I'd rolled over facing Matt. I kissed Matt, and he kissed me back and began stroking my body. We spent a recollective meter necking and touching each other before we got up and went to the cascade 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 tool, I got down on my stifle and sucked him off again. With my make-up off and whisker wet, I didn't look quite the Sami, but I dried my hair, styled it as topper I could and got dressed in my dress from utmost night. I had a little physical composition in my purse and could do lipstick, eyeliner and a piffling base, to pull in me more like Lynn.

The more I looked like Lynn, the Sir Thomas More matt seemed to be lovesome. He fucked me once more before taking me home base, and we made a date for that evening.

When I got home, I looked at myself in the mirror, then just slumped onto the couch and shook my head. I could finger 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 to the lowest degree, I guess I was Lynn, until Matt got tired of me or I got tired of it all. I guesswork Karen's extra clothes were now Lynn's clothes till foster notice.

Matt took me out again Saturday night, and took me back to his place. We were not as wear out or rummy and after I went down on him, he fucked me three multiplication. I enjoyed it but as I drifted off to log Z's, I was starting to experience contravene. Was this really how I wanted to be out my life ? And how long was Matt belike to be concern in me ?

We fucked a couple more time the side by side morning and I went dwelling. I decided that Lynn would only be on Fri and Saturday nights. I was going to live and work as Lenny, the balance of the time. It was hard. We all want to be appreciated. We all want someone to intend we are exceptional. Lenny is n't special to anyone, though Lynn is.

Occasionally during the workweek, I would be Lenny and go out as Matt 's wingman. matt always found an attractive fair sex to take house. I was a little jealous - both of lusterlessness and of the cleaning lady. On uncommon occasion, I 'd be Lynn during the week, and Matt would arrive to my post to sleep together me. Usually Lynn was a weekend thing, but some weekends, Matt had other plans.

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

One Friday nighttime, flatness and I were at a nine and I was being Lynn, though Matt seemed to be giving to the highest degree of his attention to a very moderately blonde. I sat there feeling pretty neglected, when Nicole came up to blab to me. Nicole was a brunette, about my age, a bit taller, but with a very gracious shape, b-cup boobs, and a pretty face.

'' wellspring, dear, your date seems to be ignoring you. ``

'' I guess I 'm old tidings. ``

'' Foolish 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 mat and I have kind of an unusual relationship. ``

'' wellspring, your guy appears to be about ready to step out with another charwoman. Would you stimulate any interest in doing the same ? Or are you strictly into guy ? ``

'' You mean ... you 're interested in fair sex ? ``

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

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

Nicole reached up, and stroked my facial expression. I 'd shaved as cleanly as I could before going out with flatness, and my facial nerve hair is not thickheaded, but there was the svelte trace of very light up stubble 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 line. ``

'' And you like that ? ``

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

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

Nicole took my hand and led me out onto the dance storey. I glanced back at Matt and he was so fixated on the blonde that he never even noticed that I left. We did a couple of degenerate dances, and I really enjoyed dancing with Nicole. Hell, as Lenny, I had trouble getting women to even dance much with me.

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

At the end of the dance, Nicole gave me a buss that almost buckled my knees. I could feel my cock getting gruelling 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 char kiss me like that before, and I was in no hurry for it to end.

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

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

"Well, I guess I don't nous, 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 osculation. We finished our deglutition, danced a bit more then Nicole invited me back to her place. Nicole was an inside sales rep for a technical school party. She worked near where I did and made some decent money. I was still amazed that she had any interest in the likes of me.

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

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

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

"So maybe you never met the right girl before. As long as you're open minded and elastic, I think we can have hatful of fun."

I felt a little uncertain. Nicole was pretty and she seemed willing. I just didn't understand why she'd have any interest group in me - not after knowing that I was a guy dressed as a girl who'd been out with a guy. spirit, I'd never had any woman willing to commit me the clock time of day, much LE get intimate with me. Nicole figured out what I really was and still seemed matter to. Now that was kinky.

lustrelessness had left me and gone off. I could either call an Uber or find out what Nicole had in head. Honestly it was probably safe than what Matt had done, even though I seemed to enjoy fucking Matt. I sat for several second gear, just pondering the possibilities. I looked at Nicole who sat there with a minuscule enigmatic grin on her fount, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

"Why not ? If I'm walk on the idle side of meat anyhow, why not take the air a little farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the society. She had a car nearby, zilch as expensive or flashy as mat's BMW, but a Nissan 370Z a couple of geezerhood 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 woman and knew what I was down below.

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

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

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

"Better than your little boyfriend ?"

"No question."

We were stopped, getting ready to get out 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 2nd storey and we had to walk a flight of stair, but we had our arms around each other, giggling and petting each other as we went.

Nicole had a nice little one bedroom berth, clearly feminine, with a tone down floral sofa and chairman, along with some art prints on the walls. The photographic print were largely of women and men, along with a few where it wasn't quite sack if it was male or female. She walked me over and we sat on the sofa, and she put her arm around me.

"So when did you take in that you were Lynn ?"

"I really just started dressing up in my sister's clothes as a turn-on. I told mat one sentence when I was drunk and he wanted me to tog up for him."

"Obviously, you did."

"He liked the way I looked and wanted to take in 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 guys ?"

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

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

"Never. about 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 lovemaking 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 lilliputian boyfriend matt ?"

"I think he's getting a slight sap 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 afterwards tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the foresightful sentence. I wanted More of course, but I didn't want to speed things and discomfit her and maybe defecate her send me on my way. Nicole stroked my body, mostly back, blazonry, and ass, so I followed her lead and did the same to her. After a retentive stretchiness of kissing and touching, Nicole stopped.

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

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

Nicole took one of my hands and placed it on her titty over her bra. I think my centre must have gotten very spacious. She smiled, then leaned forward and kissed me as I held her booby. I wasn't sure where she was setting demarcation, but I couldn't help but rub her knocker through her bra. Nicole moaned and continued to kiss me.

My bra, of grade, was filled with padding, not blunder, but she began to stroke me through my bra anyhow. Even though she was not touching me, only the padding, it still sent a shake of pleasance through my body. She had both deal on what would cause been my boobs, if I had any, so I placed my other hand on her other breast.

I was a little concerned about pushing it too far, but Nicole seemed to get even more release on. We continued like this for a piece before she asked me to unhook her bra. I had been fastening and unfastening the ones I wore for some metre, 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 sleeve 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 admit our bras to fall off each of us.

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

Her boobs felt amazing, warm, soft, and just so marvelous. I began to fondle her dummy and tit as Nicole played with my chest. After a footling while, she stopped kissing me and guided my mouth down to one of her scrumptious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the boob right hand on her nipple.

Nicole leaned back, pulling me with her as I began to kiss and lick her titty 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 knocker seemed to revel in my attention. After a bit, she shifted my headland over to the other dumbbell, and I began to founder it the same attention that I'd been giving its partner.

I spent a long time fondling and pleasing her knocker, 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 send me on my way. Instead Nicole stood and pulled me to my understructure and led me by the hand into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, sister, unzip my skirt."

I unzipped her and she let the dame slide down her body onto the floor. She stepped out of the skirt, then kicked off her place. She now wore only scanty, and I could see a decidedly wet blot in the front of them, as Nicole unzipped my skirt. My panty 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. OK ?"

"Anything you want, Nicole."

"First, take 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 gain of her ass, she dropped her hips back to the bed and lifted her ft, letting me take them completely off her. Nicole spread her branch and for the for the first time time I got to see a woman's puss. Nicole had shaved most of it, except for a narrow down strip just above her labia. Nicole gently pulled my head to her nether regions, though I had no theme what I was supposed to do.

"Okay, infant. 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 lip and moaning. My face was wet with her juice 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 coxa, so I raised them off the bed, and she pulled off my step-in.

I was still in wax makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my scanty off, she kissed the drumhead of my prick, which was as hard as I've ever seen it. Look, I'm no great milkshake in that department, but I've got about six inches, and it was in its wax glory as Nicole slid back up my body.

I could palpate my dick, sawing between her thigh, even rubbing across her pussycat backtalk as Nicole writhed around on me. Finally, she lifted her hips, grabbed my prick and guided it into her sweet pussy. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was 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 cerebrate you like this ?"

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

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

Nicole began moving her coxa 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 aright. I'd spent so much time jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her boobs and fondled her ass. After a patch, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it baby, correct inside me. Fill me up with it."

As I started to cum, I grabbed her ass and held her soaked 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 grand. Better 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 strap. She came back over to the bed and strapped it on herself, so it now appeared that she had a hawkshaw. She had me get on men and knees, then got some lubricator from a nearby drawer, before lubing up the penis and my ass.

Nicole eased the thing 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 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 restrain going a lot farseeing than Matt 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 gimmick on her even through that. We kissed for a recollective clock time before she turned me on my slope and spooned me, with her strap-on press up against my ass. We fell asleep that way and I had the most contented sleep that I've had in ages.

………………………………………………………………………………..

We woke up in the morning, still spooning that way. Nicole and I kissed before she fucked my ass again, and then took that off and let me make out 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 program for tonight, Lynn ?"

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

"That sounds enceinte. I've got some errands and matter to do this afternoon, so you need to get your cunning little ass house, 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 trouble with that ?"

"Not as long as I can expend my time with you."

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

I put my clothes back on. All I had was Lynn apparel, so I wore those and did my make-up 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 telephone rang - a call from Matt.

"Hey, babe. Sorry I left you live 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 consecrate you a lift home or you'd apprehension an Uber or something."

"Actually, she took me back to her place, and I spent the Nox 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 raging than Toni."

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

"Come on, young lady. 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 girl, but she's got devices. I'm not missing out on anything, and I'm getting matter I could never get with you. I get to play with boobs, I get to fuck a pussy."

"Are you fucking dumping me, bitch ?"

"Matt, you've been a well supporter, 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 farsighted as I can."

"I give it two weeks at the outside."

"wellspring then, I'll take that two calendar week. 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 hybridization vanity, you also out yourself as fucking a guy who cross dresses. Your trivial girlfriends might not bring 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 dumps me, if you aren't too big a bitch, you might even get more. In the lag, I hope you have a great evening."

So who was I ? Who did I want to be ? Matt only wanted me as Lynn, and it was starting to look like Nicole did too. The deviation 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 option, I'd rather be with Nicole or some other woman than to be with Matt.

I guessed I was epicene enough to get off on what I did with mat, but why give up on char if I had any luck with them ? I was still sitting there in clothes 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 metre. I was a little leery of opening the doorway, when it was unlocked from outside.

I sat there shocked as my sister Karen came in the flat. She didn't point me immediately, but turned to fill up and lock the threshold. She saw me and her mouth hung open and she seemed frozen 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 piece of ass ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my panty and bras too ?"

"I am."

"I got a bigger blank space and was going to peck up the relief of my wearing apparel, 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 glad ?"

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

"A girlfriend ? A real girl ? Not some in between or cook matter ?"

"Nicole is a literal adult female. For some rationality she gets off on being with me like this."

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

I looked at my shoes. I couldn't look Karenic in the face. She understood immediately.

"shtup. 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 incur another woman, you'll go back to fucking guys ?"

"Karen, please."

"Lenny, it's your lifetime. nooky who you want. Just don't display up at dwelling house or my station 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 same fourth dimension, I needed have sex too, and if being Lynn was what kept Nicole then I was going to stay to be Lynn. I wept on Karen's shoulder, and she took some pathos on me and stroked my head and tried to soothe me. It took a spell before I regained my composure.

"The real number kick 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 order to get off."

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

"So you dressed this way to get guys ?"

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

"And this female child you're with now ?"

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

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

"I don't do it how long it'll last, but I'll do what I have to do to keep 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 lady friend. And I'm not going to outwear any of the clothes I left here, so they're all yours."

Karen left, and I went in the bath to fix my war paint and then changed wearing apparel. I'm not sure where the kinship with Nicole will take me, but I guess meter will tell .