It started form of strange. I am or at least was Len or Lenny - Leonard to my mother - a guy in my former 20s, variety of short and slender. I had a sister, Karen who was a few years older than me. She'd had a nasty breakup with a fiancé, and stayed with me for a piece when she was trying to put her life story back together.

It was a bit inconvenient, since I just had a one sleeping room plaza, 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 loo, leaving little room for my clothes. Beyond that, we had to share one tiny bathroom, in shifts, since there was no way we were going to be in there at the same time - too pocket-size and too weird.

Karen stayed with me for about six months before getting her own property and moving out. Her place was belittled than mine, so while she took about of her hooey, she had more clothes than she had room for in the new station. She didn't want to donate them, so she asked if she could leave them at my place until she could afford a bigger space. Again, being a skillful brother, I let her do it.

Karenic left behind all manner of things, skirts, frock, blouses, brassiere, panty, shoes, composition, and all that. After I while I got fascinated with it, which I guess was my outset mistake. I started by just touching some of the clothes. I was a moderately nerdy guy who could never get anywhere with char, so even touching the clothes was a turn-on.

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

As time went on, I'd prune up completely in Karen's dress for my self-abuse academic session, and even left them on after I'd cum. I began to recreate with it all a little bit and even began to use some of the makeup she'd left behind. I'd pad her bras with socks or whatever, put on scanty, a skirt, blouse, and shoes, then brush my fuzz in a to a greater extent womanly vogue and learned how to do my makeup.

It all seemed innocent. I was in my place, by myself, using it all as part of self-stimulation. perdition, I needed to get off too, and there were no missy uncoerced to serve me. Before longsighted, I'd come home from piece of work, dress up all girly, and prance around my flat before getting myself off. I'd even wear one of Karen's old gown to bed afterward.

I had a few friend who I'd hang out with occasionally. One of them, who I'd known since gamey school was lusterlessness. He was always the popular sort, never had any problem getting girlfriend, and often seemed to stimulate one or to a greater extent hanging off him. He'd take me along as a wingman sometimes, though I never managed to get any daughter out of it.

One nighttime he and I were drinking, and I'd had More than I should ingest, and we began talking. He started telling me about how he got some bird to let him finger her in public in a restaurant. He said they'd also gone to a movie theater, sat way in spinal column, and she hiked up her annulus, sat on his lap, and fucked him in the theatre during the movie.

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

"bastard, lustrelessness, I can't get fille to do ordinary tinker's damn with me, much less anything kinky."

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

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

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

"Sometimes I'll go full drag, clothes, shoes, physical composition, and everything."

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

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

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

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

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

That was Thursday, and it was already late and I was too drunk and had to work the adjacent day. He asked if I'd dress up for him the next night. I agreed and told him to add up by after study on Friday, but to give me some time to get ready.

"Lenny, do you remember you can be make in an 60 minutes ?"

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

…………………………………………………………………………

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

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

I wore some low heels with give toes, to demonstrate 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 spooky when the doorbell rang at seven o'clock. My knees were wobbly as I walked to the door. I looked through the spyhole and certainly sufficiency it was matte. I opened the threshold and let him in.

Matt was gaping and staring as he walked in my place. I closed and locked the door and he turned me around then stepped back to hire a good aspect at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me nervous. He came back in front line of me and grabbed me gently by the shoulders.

"hoot, that is hot, girl."

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

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

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

"Hold 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 little 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."

Matt put and arm around me fuddled and walked me over to the couch, pulling me down beside him there. He had his arm around my articulatio humeri and seemed to be getting way too much delight out of this.

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

"flatness, this feel really weird."

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

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

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

"You've got draw of girls - real daughter, not fake ones, like me."

"Don't tear yourself down. virtually of those girlfriend have nothing on you."

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

"Let me take you out to dinner, Lynn"

"Just let me change into some normal wearing apparel, 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 mortal sees me - recognizes me ?"

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

"Doesn't it bother you to be out in world with a guy in retarding force ?"

"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 delicacy you the way a lady should be treated."

"That makes me feel really weird."

"And maybe a minuscule turned on ?"

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

"I do, and we should."

With that, Matt got up and pass me to my feet. He wrapped his arms around me and pulled me confining. I think my optic were the sizing of discus and my knee were getting infirm as he leaned forward and kissed me on the cheek. He let go with one arm and walked me to the door. When we got there, he stopped and turned.

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

"I think Karenic left a couple of handbag here too."

"Grab one and your paint 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 closet and found a bag that didn't look too bad with what I was wearing. I took my keys and wallet and dropped them in the purse before turning to Matt.

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

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

Matt actually had money, which is yet another reason why about of the girls fell all over each other to get to him. We went downstairs to his mark new grim BMW Z4 exchangeable and he opened the door of the car for me. I managed to sit down in a somewhat ladylike fashion - I don't think I showed too a great deal. He got in and ride us to a very nice restaurant.

He used valet parking and walked me in, holding the doorway for me. I still felt Wyrd as jack, but just tried to ignore how I looked and relish myself. Matt ordered a nice nursing bottle of wine-coloured for us, and I really needed something to drink in. I downed my first glass before he'd taken more than a partner off sips of his wine-colored. Matt poured me another glass, but I took it a fiddling slower.

The waiter seemed very taken with me, and when he thought I didn't notification, tried looking down my blouse. respective early men seemed to notice me, which made me squirm in my keister. One guy who works with Matt stopped at the table to talk with us. I'd met him several times before, but he clearly didn't recognize me.

"wellspring, Matt, who is this beautiful noblewoman with you tonight ?"

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

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

"And I'm very pleased to touch you, Lynn. matt is clearly a very favourable man. But if you want a alteration of scenery, ease up me a call, I'd love to show you a safe time."

With that, Oliver handed me a clientele 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, feel free to send her my way."

Oliver bent down and kissed my cheek before walking off.

"I do not fucking believe that."

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

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

We had a lovely dinner and I continued to wassail way more than I should have. This hale scene had blown my mind so a lot I didn't know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate aid to me, when they stopped to babble to lustrelessness. We finished dinner and I thought matt would take on me back to my place.

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

"Are you sure about that ?"

"You're taking a base on balls on the wild side, just rent a bit longer walk."

lustrelessness wouldn't take ‘ no'for an answer and drove us to the live club in town. This was the sort of place that would never let the ilk of me inside. They must have had a one C citizenry lined up waiting to get in. matte 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 drink and then Matt wanted to dance with me. I felt strange as shit, but it was a fast bit and I was already half plastered so I went out to dance with him. We danced several firm dances, then a sluggish number came on. I thought we'd go sit down, but instead, Matt pulled me close to him to dance.

He had one helping hand on my upper berth back, holding me smashed, as his early mitt came down on my ass. He began to fondle my ass, which made me wriggle. I could feel that lustrelessness had a hard-on as he did that. That scared me Sir Thomas More than a lilliputian, but I wasn't sure as shooting what I could do. I felt incapacitated as we danced. When the turn ended, Matt stopped, held me tight, and kissed me.

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

I'd been drinking pretty sound before, but I didn't slow down down. I was one-half afraid of what was going to find, and felt like I needed to be very drunk. We drank more and danced Thomas More, and the more we drank and danced, the to a greater extent flatness kept feeling me up and kissing me. My mind was blown - Matt knew I was a guy dressed like a cleaning lady, yet he was acting like I was the real thing.

As I said, I'd been Matt's wingman more than a few times, and had seen him this way with women many times before. I also knew that in nearly display case he ended up taking those womanhood place 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 longsighted we danced and drank, but by the clip Matt was quick to leave, I was really plastered.

I thought Matt was going to drive me back to my topographic point, but instead he drove me to his apartment. As I said, Matt had money, and he had a very nice two bedroom flat - nice piece of furniture and all that. part of me hoped that he was going to let me crash in the spare bedroom. Another theatrical role of me wanted anything but that.

"mat, I really demand to get menage and change."

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

lusterlessness got us each a boozing, like I needed any more alcohol, and sat me down on the lounge, sitting right alongside me. Matt put his arm around me and pulled me tight, then began to osculate me. He started just with the sass, then added in some glossa, while feeling up my ass and my fake dumbbell. I seemed to be enjoying it, but felt that it was wrong.

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

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

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

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

"What… What did you want me to do ?"

"If nothing else, can you at least go down on me ?"

"You want me to… ?"

"Please, Lynn, baby."

lusterlessness kissed me and stroked my ass as he unzipped his drawers with his other hand. He pulled out his dick, which was already hard and standing straight up. He kissed me again, then gently pushed my headland down toward his dickhead. I got fill up 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 caput of his prick between my lips.

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

I slowly but steadily fucked his stopcock with my mouth and flatness seemed to like it. Some precum came from the tip, and it had a salty taste, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the al-Qa'ida of his tool as I sucked the rest of it. By now, Matt was moving his hips, almost fucking my mouth, as he held my head tight.

lustrelessness moaned loudly and got very fixed as his dick erupted in my mouth. He held my head with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for hint, though it took a duet of swallow to get it all down. It gradually eased and I cleaned his cock off as I pulled my head back from it.

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

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

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

"Do it, Matt. Do it."

matt set me down on his bed on my hands and knees and pulled down my panties. My cock, which had been ignored for so prospicient sprang to attending, but Matt was matter to in other things. He took off his pants and shirt and got in bed behind me. He reached into a draftsman in the tabular array beside the bed and got a tube of lube.

Matt rubbed lube over his shaft, then onto a finger which he eased into my ass. It hurt a bit going in, but my ass relaxed and he was able to move it pretty freely after a hour or two. He snuck a second finger's breadth in and began to feel fuck my ass, and in spite of myself, I began to fuck him back. Matt leaned down and kissed the spinal column of my neck opening as he pulled his fingers out of my ass.

I felt the head of his rooster at my SOB and tensed for just a second before relaxing. At this period, 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 of him in me. It hurt a bit, but matte took it loose and slacken at firstly, until I really started to get into it.

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

Matt slid his hawkshaw in me so far, I could almost sense 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 solidus of his putz. I wanted his dick in my ass, and when he came with a gush in me, I came right onto his bed.

lusterlessness collapsed onto me and I collapsed and we rolled onto our slope, with his prick still inside me. I was on a sexual high school and wanted aught more than to keep feeling his hammer in my ass. His tool was getting softer, but I wanted to keep him in me as long as I could. As we came off our high gear, Matt began to stroke my shoulders and kiss the back and incline of my neck.

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

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

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

Essentially, matte 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 as a lot of him in me for as longsighted as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the side by side forenoon with flatness still spooning me and with his hard cock pressing up against my ass. Something had changed. If I'd woken up yesterday with a guy's hard putz 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.

lustrelessness woke up and began stroking me and kissing the backbone of my neck as he eased around so his prick was up against my bunghole. I could experience it and wanted it back inside me. I reached around, grabbed his stopcock and guided it into my ass, as we lay on our incline. It was a gentler fucking, instead of the pound that we had at the end last dark, but I still loved it.

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

"Lynn, infant, thank you for last night, and for this morn too."

"I hope we'll have more than 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 peter 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 post of Lenny. I need to be Lenny at work."

By then, Matt's dick had slipped out of my ass and I'd rolled over look flatness. I kissed Matt, and he kissed me back and began stroking my consistency. We spent a long time kissing and touching each former before we got up and went to the shower together. Without my clothes, my bra, my panties, I looked more like Lenny, but we washed each other, continuing to kiss.

After we washed off his hammer, I got down on my knees and sucked him off again. With my makeup off and hair wet, I didn't spirit quite the Saami, but I dried my hair, styled it as topper I could and got dressed in my clothes from death Night. I had a little makeup in my purse and could do lipstick, eyeliner and a little floor, to arrive at me more like Lynn.

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

When I got home, I looked at myself in the mirror, then just slumped onto the couch and sway my psyche. 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 on it out along the way. For now, at least, I guess I was Lynn, until Matt got tired of me or I got tired of it all. I estimate Karen's duplicate clothes were now Lynn's clothes till boost notice.

lustrelessness took me out again Sabbatum dark, and took me back to his place. We were not as tired or drunk and after I went down on him, he fucked me three meter. I enjoyed it but as I drifted off to sleep, I was starting to feel conflicted. Was this really how I wanted to live out my life ? And how recollective was Matt potential to be interested in me ?

We fucked a couple more sentence the future sunup and I went home. I decided that Lynn would only be on Friday and Saturday dark. I was going to subsist and make for as Lenny, the residue of the time. It was hard. We all want to be appreciated. We all want mortal to think we are peculiar. Lenny is n't special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as Matt 's wingman. Matt always found an attractive woman to take plate. I was a petty jealous - both of Matt and of the woman. On rare function, I 'd be Lynn during the week, and Matt would come to my place to have it away me. Usually Lynn was a weekend thing, but some weekends, mat had former plans.

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

One Friday night, Matt and I were at a clubhouse and I was being Lynn, though Matt seemed to be giving most of his care to a very pretty blonde. I sat there feeling pretty neglected, when Nicole came up to talk to me. Nicole was a brunette, about my age, a bit taller, but with a very prissy physique, b-cup dummy, and a pretty face.

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

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

'' Foolish guy. If you were mine, I would n't underprice you like that. By the way, my gens 's Nicole. ``

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

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

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

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

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

Nicole reached up, and stroked my look. I 'd shaved as cleanly as I could before going out with Matt, and my facial nerve hair is not dense, but there was the little trace of very Light stubble and I could severalise by her expression that she felt it. Nicole leaned forward and kissed me.

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

'' And you like that ? ``

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

'' I like fair sex, 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 dances, and I really enjoyed dancing with Nicole. underworld, as Lenny, I had trouble getting adult female to flush dance lots with me.

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

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

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

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

"well, I guess I don't psyche, at least as long as I have you for company."

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

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

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

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

"I like female child, I just never had much luck before."

"So maybe you never met the right girl before. As long as you're outdoors minded and flexible, I think we can get dozens of fun."

I felt a footling uncertain. Nicole was pretty and she seemed willing. 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. expression, I'd never had any woman volition to give me the clock time of day, much less get intimate with me. Nicole figured out what I really was and still seemed interested. Now that was kinky.

Matt had left me and gone off. I could either name an Uber or find out what Nicole had in thinker. Honestly it was probably meliorate than what Matt had done, even though I seemed to enjoy fucking flatness. I sat for several second base, just pondering the possibility. I looked at Nicole who sat there with a little oracular grin 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, cipher as expensive or showy as flatness's BMW, but a Nissan 370Z a yoke 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, lustrelessness 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 way. Before she closed the car door, Nicole leaned over and kissed me. She came around, sat down in the driver's prat and started the car. Before she put it in gear, she smiled at me again and gave me a warm kiss.

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

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

"Better than your little boyfriend ?"

"No question."

We were stopped, getting cook to exit the parking lot. I leaned over and gave Nicole a kiss. She smiled and stroked my head, before taking us out on the road. She drove us a few miles to her apartment. It was on the second base and we had to walk a flying of stairs, but we had our branch around each other, giggling and petting each early as we went.

Nicole had a courteous little one bedroom lieu, clearly feminine, with a muted floral sofa and chairs, along with some art photographic print on the rampart. The mark were largely of cleaning lady and men, along with a few where it wasn't quite clear if it was manly or female. She walked me over and we sat on the couch, and she put her arm around me.

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

"I really just started dressing up in my sis's apparel as a turn-on. I told Matt one time when I was drunkard and he wanted me to dress up for him."

"Obviously, you did."

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

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

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

"But you were into guy ?"

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

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

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

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

"I'd passion 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 beau Matt ?"

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

"What if he isn't ?"

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

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

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the longest prison term. I wanted more of line, but I didn't want to hasten matter and upset her and maybe make her send me on my way. Nicole stroked my organic structure, mostly back, arms, and ass, so I followed her tip and did the same to her. After a long stretch of kissing and touching, Nicole stopped.

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

I was more than happy to do so, though my manus were shaking as I began to untie the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her chick, and she asked me to pull it loosen and subscribe 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 men and placed it on her breast over her bra. I think my eyes must have gotten very wide. She smiled, then leaned forward and kissed me as I held her boob. I wasn't sure where she was setting terminal point, but I couldn't help but rub her boob through her bra. Nicole moaned and continued to snog me.

My bra, of course of instruction, 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 shiver of pleasure through my physical structure. She had both hands on what would possess been my bosom, if I had any, so I placed my other hand on her other breast.

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

I rubbed her back where the bra had been, and Nicole moaned and squirmed, then shrugged, which let the bra declination forward. She had her weaponry 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 snog for a patch before she leaned back to reserve our bandeau to precipitate off each of us.

My bra and padding fell to the floor, leaving my bare breast out there. I got my initiatory look at Nicole's breasts - actually the initiative titty I'd ever seen live and in person. I wanted to adjoin them but I was hesitant. I didn't want to move too fast and thwart things. Again Nicole put my hand on one of her booby, then began to stroke my flat, boobless, chest.

Her boobs felt gravel, warm, soft, 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 backtalk down to one of her delicious knocker. I looked up at her, and she smiled at me, so I moved forward and kissed the breast right on her nipple.

Nicole leaned back, pulling me with her as I began to snog and cream her boob 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 white meat seemed to whoop it up in my attention. After a bit, she shifted my head over to the other boob, and I began to grant it the like attention that I'd been giving its partner.

I spent a long time kissing and pleasing her breast, 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 feet and led me by the handwriting into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, baby, unzip my skirt."

I unzipped her and she let the skirt slide down her physical structure onto the floor. She stepped out of the skirt, then kicked off her shoes. She now wore only panty, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my skirt. My panties were having trouble restraining my mother fucker, 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. okey ?"

"Anything you want, Nicole."

"First, learn off my panties."

I moved down her soundbox and Nicole lifted her pelvis off the bed. I slid her panties down and once they were discharge of her ass, she dropped her hips back to the bed and lifted her fundament, letting me take them completely off her. Nicole spread her ramification and for the foremost sentence I got to see a woman's pussy. Nicole had shaved most of it, except for a narrow strip just above her labia. Nicole gently pulled my head to her chthonic area, though I had no theme what I was supposed to do.

"Okay, baby. kiss it, lick it, stick that lingua in me."

Nicole directed me as I ate her out, until she wrapped her peg around my read/write head, almost crushing me, while humping my oral cavity and moaning. My cheek was wet with her succus as she released me, then pulled me back up to buss me. We kissed for a piece, 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 scanty.

I was still in fully makeup as Lynn, even if I basically looked like Lenny from the neck down. As she pulled my panties off, she kissed the nous of my peter, which was as concentrated as I've ever seen it. Look, I'm no swell shakes in that department, but I've got about six inch, and it was in its full glory as Nicole slid back up my body.

I could feel my dent, sawing between her thigh, even rubbing across her twat lips as Nicole writhed around on me. Finally, she lifted her hips, grabbed my son of a bitch and guided it into her sweetness pussy. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was thick inside her. Once in, she paused a bit, getting us both used to the look 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 celebrate 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 heaven, and wished it could never end, even if I knew she was correct. I'd spent so a good deal time jerking off that I didn't cum immediately. She continued fucking me and kissing me as I played with her booby and fondled her ass. After a while, I realized I was getting close.

"I'm going to cum, Nicole."

"Do it cocker, in good order inside me. Fill me up with it."

As I started to cum, I grabbed her ass and held her rigorous and as close to me as I could. I filled her with my cum until I had no more to afford. 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. Better than anything I've ever done with Matt."

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

"What do you mean."

Nicole got off me, got up and walked over and opened a 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 genu, then got some lube from a nearby draftsman, before lubing up the penis and my ass.

Nicole eased the matter into my ass, until I was well-off 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 compass point, I wasn't going to reason with her. As she began fucking me, I began to get into it. For obvious understanding, she was able to stay fresh 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 twist on her even through that. We kissed for a long meter before she turned me on my slope and spooned me, with her strap-on pressing up against my ass. We fell asleep that way and I had the most contented rest 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 fuck her pussy. We showered together, playing as we washed each other. I went down on her in the exhibitor and she went down on me after.

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

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

"That sounds great. I've got some errands and things to do this good afternoon, so you need to get your cute picayune 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 pass my fourth dimension with you."

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

I put my clothes back on. All I had was Lynn dress, so I wore those and did my constitution before I left. I got back to my apartment and sat on the lounge, just amazed at the hold out 24 hours. While I sat there, my headphone rang - a cry from Matt.

"Hey, infant. Sorry I left you hold out 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 get up domicile or you'd gimmick an Uber or something."

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

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

"Yeah, she was."

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

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

"You're live than Toni."

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

"Come on, young woman. If it weren't for me, you'd have had no sex life and no prospect at that Nicole."

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

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

"She's all little girl, 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 bring with boobs, I get to have a go at it a pussy."

"Are you fucking dumping me, crab ?"

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

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

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

"I give it two calendar week at the outside."

"Well then, I'll take that two weeks. 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 cross dresser, you also out yourself as fucking a guy who cross attire. Your petty girlfriends might not look at that very well."

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

"And you've dumbfound defrayment for that. And if or when Nicole plunge me, if you aren't too big a bitch, you might even get more than. In the meantime, 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 departure 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 char than to be with Matt.

I guessed I was bisexual enough to get off on what I did with matte, but why give up on charwoman if I had any chance with them ? I was still sitting there in apparel as Lynn, when there was a belt on the room access. I was puzzled, because I wasn't expecting Nicole, Matt, or anyone else for some time. I was a little 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 bit me immediately, but turned to fill up and operate the door. She saw me and her back talk hung open air and she seemed frigid in position until she began moving slowly toward me. Karen got over to me, reached out a hand and touched my face.

"Lenny ? What the roll in the hay ?"

"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 variety of a long story."

"Are you wearing my panties and bras too ?"

"I am."

"I got a grown place and was going to pick up the rest of my dress, 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 well-chosen ?"

"Not especially, but it makes the young woman I spent the nighttime with happy."

"A girl ? A real female child ? Not some in between or fudge thing ?"

"Nicole is a substantial char. For some reasonableness she gets off on being with me like this."

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

I looked at my shoes. I couldn't look Karen in the aspect. 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 find another adult female, you'll go back to fucking guys ?"

"Karenic, please."

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

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

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

"I hope you can understand and forgive me."

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

"You were always popular with the Guy. I could never get any of the girls to contribute me a s look."

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

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

"And this girl you're with now ?"

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

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

"I don't know how foresighted it'll utmost, but I'll do what I have to do to hold on it going."

"Should I still call you Lenny ?"

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

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

Karen left, and I went in the lavatory to fix my composition and then changed dress. I'm not sure where the relationship with Nicole will rent me, but I guess prison term will tell .