It started kind of strange. I am or at least was Len or Lenny - Leonard to my mother - a guy in my early 20s, kind of short and slender. I had a sis, Karen who was a few years older than me. She'd had a smutty breakup with a fiancé, and stayed with me for a while when she was trying to put her animation back together.

It was a bit inconvenient, since I just had a one bedroom berth, and not all that big. Being a courteous piffling brother, I let her possess the bed, while I slept on the sofa. She had a ton of clothes and more than filled my closet, leaving petty way for my dress. Beyond that, we had to contribution one tiny bathroom, in break, since there was no way we were going to be in there at the same metre - too small and too weird.

Karen stayed with me for about six calendar month before getting her own place and moving out. Her blank space was smaller than mine, so while she took well-nigh of her stuff, she had more wearing apparel than she had room for in the new place. She didn't want to donate them, so she asked if she could bequeath them at my space until she could afford a bigger place. Again, being a prissy chum, I let her do it.

Karenic left behind all mode of affair, skirts, garb, blouses, brassiere, step-in, skid, composition, and all that. After I while I got fascinated with it, which I dead reckoning was my initiative mistake. I started by just touching some of the clothes. I was a pretty nerdy guy who could never get anywhere with women, so even touching the clothes was a turn-on.

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

As time went on, I'd set up completely in Karen's dress 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 physical composition she'd left behind. I'd pad her bras with socks or whatever, put on panties, a skirt, blouse, and shoes, then sweep my hair in a more feminine manner and learned how to do my makeup.

It all seemed impeccant. I was in my place, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no girls will to help me. Before tenacious, I'd come plate from work, do up all girly, and prance around my flat before getting myself off. I'd even wear one of Karen's old nighties to bed afterward.

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

One night he and I were drinking, and I'd had Sir Thomas More than I should have, and we began talking. He started telling me about how he got some wench to let him finger her in populace in a eating place. He said they'd also gone to a movie dramatic art, sat way in binding, and she hiked up her chick, sat on his lap, and fucked him in the theater during the movie.

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

"Shit, mat, I can't get female child to do ordinary shit with me, much less anything kinky."

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

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

"Seriously, Len. Do you just luxate on her panty to get turned on or do something more than ?"

"Sometimes I'll go full phase of the moon drag, dress, brake shoe, make-up, 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 hold someone see me."

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

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

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

That was Thursday, and it was already late and I was too drunkard and had to work the following day. He asked if I'd dress up for him the next nighttime. I agreed and told him to come by after work on Friday, but to render me some time to get ready.

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

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

…………………………………………………………………………

The next day I really had some ruefulness about agreeing to let him see me dressed up. I called him during lunch and tried to second out, but he said I'd promised and he expected me to maintain my promise. I was on edge all afternoon. I got home about six and took off all my dress. I swear I was shaking as I cleaned up, showered with scent consistency wash, shaved my face, leg, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the persuasion of having this guy see me in my sister's clothes. I dried my hair and styled it girlish, then put on panties, a bra, a nice bird, and a blouse, then sat down to do composition. By now I had it almost to a science, putting on base, then some accent, eyeliner, eye shadow, lipstick, and of grade I painted my toenails and fingernails.

I wore some low heels with outdoors toes, to read off the toenail polish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o'clock. My knees were wobbly as I walked to the room access. I looked through the eyehole and certain adequate it was Matt. I opened the door and let him in.

lusterlessness was gaping and staring as he walked in my place. I closed and locked the doorway and he turned me around then stepped back to take a good feeling 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 skittish. He came back in front of me and grabbed me gently by the shoulders.

"shucks, that is hot, girl."

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

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

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

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

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

"While you're like this, you're Lynn, and I like Lynn. seminal fluid on, please sit on the lounge with me."

"This was a error. 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 shoulders and seemed to be getting way too much joy out of this.

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

"Matt, this feel really weird."

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

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

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

"You've got lots of girls - veridical young lady, not cook ace, like me."

"Don't tear yourself down. Most of those miss have zip on you."

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

"Let me take you out to dinner, Lynn"

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

"No, babe, just like this."

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

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

"What if person sees me - recognizes me ?"

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

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

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

"I don't know."

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

"That makes me feel really weird."

"And maybe a little turned on ?"

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

"I do, and we should."

With that, Matt got up and drew me to my feet. He wrapped his arm around me and pulled me close. I think my eyes were the size of saucers and my knees were getting weak as he leaned forward and kissed me on the 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 handbag, keys, and such ?"

"I think Karen left a twain of pocketbook 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 wardrobe and found a bag that didn't look too bad with what I was wearing. I took my tonality and billfold and dropped them in the purse before turning to Matt.

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

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

Matt actually had money, which is yet another reason why most of the girls fell all over each former to get to him. We went downstairs to his firebrand new disconsolate BMW Z4 convertible 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 repulse us to a very squeamish restaurant.

He used valet parking and walked me in, holding the door for me. I still felt uncanny as shit, but just tried to ignore how I looked and enjoy myself. matt ordered a nice nursing bottle of wine-colored for us, and I really needed something to tope. I downed my first glass before he'd taken more than a brace sips of his vino. Matt poured me another glass, but I took it a slight slower.

The server seemed very taken with me, and when he thought I didn't notice, tried looking down my blouse. Several early men seemed to note me, which made me squirm in my seat. One guy who works with Matt stopped at the table to mouth with us. I'd met him respective fourth dimension before, but he clearly didn't recognize me.

"well, matte, who is this beautiful lady with you tonight ?"

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

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

"And I'm very pleased to meet you, Lynn. Matt is clearly a very lucky man. But if you want a change of scenery, devote me a call, I'd love to exhibit you a good time."

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

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

"fountainhead, Matt, if you get tired of Lynn here, sense loose to send off her my way."

Oliver bent down and kissed my face before walking off.

"I do not fucking believe that."

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

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

We had a lovely dinner and I continued to drink way to a greater extent than I should suffer. This whole scene had blown my mind so much I didn't know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to talk to matt. We finished dinner and I thought flatness would take 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 wild English, just withdraw a bit longer walk."

Matt wouldn't take ‘ no'for an solution and repel us to the hot club in town. This was the kind of place that would never let the the likes of of me inside. They must stimulate had a hundred the great unwashed lined up waiting to get in. Matt was obviously pretty well known, and he walked us up to the front man, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a crapulence and then matte wanted to dance with me. I felt unknown as shit, but it was a dissolute turn and I was already half plastered so I went out to dance with him. We danced several dissipated dances, then a irksome identification number came on. I thought we'd go sit down, but instead, lusterlessness pulled me come together to him to dance.

He had one deal on my pep pill back, holding me tight, as his early hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that Matt had a erection as he did that. That scared me more than a short, but I wasn't sure what I could do. I felt lost as we danced. When the identification number ended, Matt stopped, held me fuddled, and kissed me.

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

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

As I said, I'd been mat's wingman more than a few times, and had seen him this way with char many clip before. I also knew that in most cases he ended up taking those fair sex base and fucking them. That scared me, but also seemed to call on me on, and it scared me that I was turned on by it. I don't know how retentive we danced and drank, but by the time matte was ready to will, I was really plastered.

I thought Matt was going to drive me back to my spot, but instead he drove me to his apartment. As I said, Matt had money, and he had a very decent two sleeping room apartment - gracious article of furniture and all that. role of me hoped that he was going to let me crash in the excess sleeping accommodation. Another section of me wanted anything but that.

"Matt, I really require to get home base and change."

"Lynn, beloved, there's no hurriedness. Just relax and enjoy your walk of life on the wild side."

matt got us each a drinking, like I needed any more inebriant, and sat me down on the sofa, sitting properly alongside me. Matt put his arm around me and pulled me tight, then began to kiss me. He started just with the lips, then added in some tongue, while feeling up my ass and my fake boobs. I seemed to be enjoying it, but felt that it was wrong.

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

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

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

"Lynn, baby, I've shown you a good metre. I've made you feel beneficial. You seem to be getting into this. Can't you help me finger good too ?"

"What… What did you need me to do ?"

"If cypher else, can you at least go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

Matt kissed me and stroked my ass as he unzipped his pants with his other manus. He pulled out his peter, which was already concentrated and standing straight up. He kissed me again, then gently pushed my head down toward his motherfucker. I got close-fitting and looked at it. It was long and hard and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the drumhead of his putz between my lips.

Matt moaned and leaned back, still keeping a hand on my head word. I let the head of his cock slip from between my lips, before taking it back and going just a fiddling farther with it. I bobbed up and down on his prick, gradually taking it deeper and cryptic into my mouth. I'd never had a gumshoe in my mouth before and it felt unknown, but in another way, it felt very natural.

I slowly but steadily fucked his shaft with my mouth and mat seemed to like it. Some precum came from the tip, and it had a salty appreciation, 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-Qaeda of his putz as I sucked the rest of it. By now, matte was moving his hips, almost fucking my lip, as he held my head word tight.

matte moaned loudly and got very set as his cock erupted in my mouth. He held my head with both custody as he emptied his lump into my pharynx. I swallowed his cum and gasped for breath, though it took a duad of swallows to get it all down. It gradually eased and I cleaned his shaft off as I pulled my straits back from it.

matte pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my backtalk as we kissed, but that didn't seem to gravel him. Matt continued to snog me and I didn't even realize it as he pulled my chick up over my ass and began to caress my ass through my panty. He even snuck his hand into my scanty and fondled my bare ass.

I don't know why I didn't observation, 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, mat had removed my annulus and blouse and was carrying me into his bedroom. I was so far gone at this head I didn't know or care, or maybe it was what I really wanted.

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

"Do it, Matt. Do it."

flatness set me down on his bed on my mitt and knees and pulled down my panties. My putz, which had been ignored for so longsighted sprang to attention, but lusterlessness was interested in other things. He took off his pants and shirt and got in bed behind me. He reached into a drawer in the board beside the bed and got a tube of lube.

Matt rubbed lube over his dickhead, then onto a finger which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able to move it pretty freely after a minute or two. He snuck a endorsement finger in and began to finger have it off my ass, and in cattiness of myself, I began to be intimate him back. Matt leaned down and kissed the dorsum of my cervix 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 peak, I think I wanted him as much as he wanted me. I felt the head get just inside me and I sighed and moved my ass back, getting more than of him in me. It hurt a bit, but Matt took it easy and slow at first, until I really started to get into it.

I soon felt his hips slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy fuck my ass, I'd have thought you were crazy and told you to pass on me the hump alone. Now Matt was fucking me and I was in heaven. I felt his dick microscope slide deep in me and take me up. It turned me on in direction I'd never have expected.

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

Matt collapsed onto me and I collapsed and we rolled onto our side, with his prick still inside me. I was on a sexual senior high and wanted nothing more than to keep feeling his pecker in my ass. His dick was getting diffuse, but I wanted to keep back him in me as long as I could. As we came off our high, Matt began to stroke my articulatio humeri and kiss the spine and side of my neck.

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

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

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

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

……………………………………………………………………………..

I woke the next sunup with Matt still spooning me and with his hard shaft pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's punishing peter 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.

Matt woke up and began stroking me and kissing the back of my cervix as he eased around so his prick was up against my bunghole. I could sense it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our English. It was a gentler fucking, instead of the hammering that we had at the end cobbler's last night, but I still loved it.

My dick got knockout as I felt his filling me up. It was a obtuse leisurely roll in the hay, almost loving, and I reached behind me to stroke lustrelessness'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 go forward as long as he wanted me.

"Lynn, baby, thank you for utmost night, and for this aurora too."

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

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

"I want it. I want your tool 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 situation 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 facing lustrelessness. I kissed mat, and he kissed me back and began stroking my consistence. We spent a long time smooching and touching each former before we got up and went to the rain shower together. Without my wearing apparel, my bra, my step-in, I looked more like Lenny, but we washed each early, continuing to kiss.

After we washed off his putz, I got down on my knees and sucked him off again. With my constitution off and hair wet, I didn't flavour quite the like, but I dried my hair, styled it as best I could and got dressed in my clothes from last night. I had a minuscule makeup in my purse and could do lipstick, eyeliner and a little radical, to hold me more like Lynn.

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

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

matt took me out again Saturday Night, and took me back to his place. We were not as tired or wino and after I went down on him, he fucked me three times. I enjoyed it but as I drifted off to sleep, I was starting to sense run afoul. Was this really how I wanted to live out my lifetime ? And how long was Matt in all likelihood to be matter to in me ?

We fucked a pair more times the side by side cockcrow and I went home. I decided that Lynn would only be on Friday and Saturday nights. I was going to last and exploit as Lenny, the rest period of the meter. It was hard. We all want to be appreciated. We all want somebody to think we are limited. 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 char to take home. I was a piddling green-eyed - both of Matt and of the woman. On uncommon occasions, I 'd be Lynn during the workweek, and Matt would come to my place to sleep with me. Usually Lynn was a weekend thing, but some weekends, Matt had other plans.

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

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

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

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

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

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

'' Well, your guy appears to be about make to step out with another woman. Would you own any interest in doing the Lapplander ? Or are you strictly into guys ? ``

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

'' I like womanhood. I like men. And sometimes I straddle the contrast. ``

'' What do you entail by straddling the contrast, Nicole ? ``

Nicole reached up, and stroked my face. I 'd shaved as cleanly as I could before going out with flatness, and my facial nerve fuzz is not thick, but there was the slightest trace of very illume chaff and I could severalize by her expression that she felt it. Nicole leaned forward and kissed me.

'' fountainhead, Lynn, something tells me that you straddle the job. ``

'' And you like that ? ``

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

'' I like woman, I 'm just ... ''

Nicole took my hand and led me out onto the dance floor. I glanced back at matt and he was so fixated on the blonde that he never even noticed that I left. We did a couple of fast saltation, and I really enjoyed dancing with Nicole. Inferno, as Lenny, I had problem getting adult female to even out dance a lot with me.

A slow turn 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 observe us or what we were doing.

At the end of the dance, Nicole gave me a kiss that almost buckled my stifle. I could feel my dick getting harder and barely being restrained by my panty. My mind was blown. We stood there kissing for I'm not even sure how long. I'd never had a woman kiss me like that before, and I was in no hurry for it to end.

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

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

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

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

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

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

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

"I like daughter, I just never had often luck before."

"So maybe you never met the right-hand fille before. As long as you're candid minded and flexible, I think we can have slew of fun."

I felt a little unsettled. Nicole was pretty and she seemed bequeath. 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 will to kick in me the time of day, much less get intimate with me. Nicole figured out what I really was and still seemed concerned. Now that was kinky.

lustrelessness had left me and gone off. I could either hollo an Uber or find out what Nicole had in judgment. Honestly it was probably better than what mat had done, even though I seemed to enjoy fucking Matt. I sat for several seconds, just pondering the opening. I looked at Nicole who sat there with a little enigmatical smile on her face, 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 of meat 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, zero as expensive or flashy as flatness's BMW, but a Nissan 370Z a couple of class 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 moment before smiling at her and sitting down in a ladylike mode. 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 appurtenance, she smiled at me again and gave me a quick kiss.

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

"C. H. Best offer I've had in a retentive time."

"Better than your fiddling fellow ?"

"No question."

We were stopped, getting fix to choke the parking lot. I leaned over and gave Nicole a kiss. She smiled and stroked my head word, before taking us out on the road. She drove us a few international nautical mile to her flat. It was on the second floor and we had to walk a flight of steps, but we had our blazonry around each other, giggling and petting each other as we went.

Nicole had a nice little one bedroom stead, clearly feminine, with a muffle floral sofa and chairs, along with some art prints on the walls. The prints were largely of charwoman and men, along with a few where it wasn't quite clear if it was male or distaff. She walked me over and we sat on the lounge, 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 wearing apparel as a turn-on. I told Matt one meter when I was drunkard and he wanted me to coiffure up for him."

"Obviously, you did."

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

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

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

"But you were into cat ?"

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

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

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

"wellspring, I like Lynn, and I might even care Lenny. How do you finger about that ?"

"I'd sexual love that, Nicole."

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

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

"What about your little fellow flatness ?"

"I think he's getting a little tired 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 More of grade, but I didn't want to rush things and upset her and maybe make her send me on my way. Nicole stroked my consistence, mostly back, limb, and ass, so I followed her jumper lead and did the same to her. After a yearn reach of kissing and touching, Nicole stopped.

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

I was more than glad to do so, though my hand were shaking as I began to undo the release. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her skirt, and she asked me to pull it promiscuous and adopt 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 oculus must suffer gotten very astray. She smiled, then leaned forward and kissed me as I held her knocker. I wasn't sure where she was setting bound, but I couldn't help but rub her boob through her bra. Nicole moaned and continued to kiss me.

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

I was a little concern about pushing it too far, but Nicole seemed to get even more ferment on. We continued like this for a while before she asked me to unhook her bra. I had been fastening and unfastening the ace 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 blazonry around me, as I had mine around her, so the bra didn't fall off. She reached behind me and unhooked my bra. We continued to kiss for a while before she leaned back to allow our bras to strike off each of us.

My bra and padding fell to the floor, leaving my bare pectus out there. I got my first expression at Nicole's breasts - actually the number 1 breasts I'd ever seen experience and in somebody. I wanted to extend to them but I was hesitant. I didn't want to locomote too fast and screw up things. Again Nicole put my bridge player on one of her boobs, then began to stroke my flat, boobless, chest.

Her boobs felt amazing, warm, easygoing, and just so wondrous. I began to caress her boobs and nipples as Nicole played with my chest. After a little while, she stopped kissing me and guided my rima oris down to one of her delicious knocker. I looked up at her, and she smiled at me, so I moved forward and kissed the knocker rightfield on her nipple.

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

I spent a recollective clip kissing and pleasing her bosom, before Nicole clutched my oral sex 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 air me on my way. Instead Nicole stood and pulled me to my metrical foot and led me by the mitt into her bedchamber. 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 trunk onto the floor. She stepped out of the skirt, then kicked off her shoe. She now wore only panties, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my bird. My panties were having trouble restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

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

"Anything you want, Nicole."

"First, carry off my panties."

I moved down her body and Nicole lifted her pelvis off the bed. I slid her pantie down and once they were clear of her ass, she dropped her hips back to the bed and lifted her feet, letting me take them completely off her. Nicole spread her stage and for the first time I got to see a fair sex's pussycat. Nicole had shaved near of it, except for a narrow down airstrip just above her labia. Nicole gently pulled my head to her nether region, though I had no idea what I was supposed to do.

"okay, sister. Kiss it, lick it, stick that spit in me."

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

I was still in wax makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the head of my prick, which was as severely as I've ever seen it. Look, I'm no bully milk shake in that section, but I've got about six in, and it was in its full glory as Nicole slid back up my body.

I could palpate my SOB, sawing between her second joint, even rubbing across her pussy lips as Nicole writhed around on me. Finally, she lifted her hips, grabbed my bastard 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 late inside her. Once in, she paused a bit, getting us both used to the flavor of me being in her.

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

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

"I don't think you can go on it up that long, but let's savor 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 good. 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 boob and fondled her ass. After a while, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it indulge, right inside me. Fill me up with it."

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

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

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

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

"What do you mean."

Nicole got off me, got up and walked over and opened a drawer. She pulled out something that looked like a 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 hands and stifle, then got some lubricant 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 get it on my ass with this strap-on. I wasn't sure I wanted her to do that, but at this point, I wasn't going to argue with her. As she began fucking me, I began to get into it. For obvious reasons, she was able to keep going a lot longer 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 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 eternal sleep that I've had in ages.

………………………………………………………………………………..

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

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

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

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

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

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

"Not as long as I can spend my prison term with you."

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

I put my apparel 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 couch, just amazed at the last 24 hours. While I sat there, my earphone rang - a call from Matt.

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

"That was Nicole. We were enjoying ourselves."

"I figured either she'd give you a hook dwelling house or you'd match an Uber or something."

"Actually, she took me back to her position, and I spent the Night there."

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

"Yeah, she was."

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

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

"You're raging than Toni."

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

"come on, missy. If it weren't for me, you'd have had no sex lifetime and no fortune 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 girlfriend, but she's got gimmick. I'm not missing out on anything, and I'm getting things I could never get with you. I get to act with boobs, I get to sleep with a pussy."

"Are you fucking dumping me, squawk ?"

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

"Lynn, how long do you guess that squawk will go before she dumps you ?"

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

"I give it two weeks at the outside."

"wellspring then, I'll take that two week. In the interim, you have Toni or one of the former many woman who fall all over themselves to be with you."

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

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

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

"And you've get payment for that. And if or when Nicole ditch me, if you aren't too big a bitch, you might even get more than. 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 calculate like Nicole did too. The difference was that I got more out of it with Nicole. It wasn't just me being fucked, I got a chance to get mine too. Fact is, given a option, I'd rather be with Nicole or some former woman than to be with Matt.

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

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

"Lenny ? What the fuck ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my scanty and bras too ?"

"I am."

"I got a big place and was going to pick up the relief 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 than stuff."

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

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

"A girl ? A existent female child ? Not some in between or fake thing ?"

"Nicole is a genuine charwoman. For some reason she gets off on being with me like this."

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

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

"Fuck. 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 come up another charwoman, you'll go back to fucking guys ?"

"Karenic, please."

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

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

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

"I hope you can see 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 pop 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 well-off, it was better than being alone."

"And this little girl you're with now ?"

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

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

"I don't know how foresighted it'll last, but I'll do what I have to do to keep open it going."

"Should I still prognosticate you Lenny ?"

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

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

Karen left, and I went in the bathroom to fix my war paint and then changed wearing apparel. I'm not sure where the family relationship with Nicole will contain me, but I guess time will tell .