It started kind of strange. I am or at to the lowest degree was Len or Lenny - Dutch Leonard to my mother - a guy in my betimes 20s, kind of short and slender. I had a sister, Karenic who was a few days sr. than me. She'd had a tight breakup with a fiancé, and stayed with me for a spell when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one sleeping room office, and not all that big. Being a decent fiddling brother, I let her have the bed, while I slept on the sofa. She had a ton of apparel and More than filled my closet, leaving little room for my wearing apparel. Beyond that, we had to share one tiny john, in transmutation, since there was no way we were going to be in there at the Lapp metre - too small and too weird.

Karenic stayed with me for about six month before getting her own place and moving out. Her place was pocket-size than mine, so while she took most of her stuff, she had more clothes than she had room for in the new piazza. She didn't want to donate them, so she asked if she could entrust them at my place until she could afford a bigger office. Again, being a decent brother, I let her do it.

Karen left behind all fashion of things, skirts, clothes, blouses, bras, panties, shoes, physical composition, and all that. After I while I got fascinated with it, which I guess was my first gear error. 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 wearing apparel was a turn-on.

I started by just touching her clothes while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my head while doing myself. After a meter, 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 braggy turn-on and her clothes seemed to fit, since we were almost the same size.

As time went on, I'd garnish up completely in Karen's clothes for my self-abuse sessions, and even left them on after I'd cum. I began to roleplay with it all a small bit and even began to use some of the composition she'd left behind. I'd pad her bras with socks or whatever, put on step-in, a skirt, blouse, and shoes, then brush my hair in a more feminine 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. Hell, I needed to get off too, and there were no miss bequeath to help me. Before long, I'd come home from work, dress up all girly, and swagger around my apartment before getting myself off. I'd even wear one of Karen's old nightgown to bed afterward.

I had a few friends who I'd hang out with occasionally. One of them, who I'd known since high school was flatness. He was always the popular form, never had any problem getting female child, and often seemed to have 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 to a greater extent than I should have, and we began talking. He started telling me about how he got some chick to let him finger her in public in a restaurant. He said they'd also gone to a movie theater, sat way in backrest, and she hiked up her skirt, sat on his lap, and fucked him in the dramatics during the movie.

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

"Shit, mat, I can't get girls to do ordinary dirt with me, much less anything kinky."

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

As I said, I'd had too a good deal to toast, and I confessed to dressing up in my sis's clothes to jerk off.

"Seriously, Len. Do you just slip on her scanty to get turned on or do something More ?"

"Sometimes I'll go wide pull, apparel, shoe, makeup, and everything."

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

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

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

"matt, if anyone ever found out, I'd be totally screwed. I'd have to impart 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 crop the side by side day. He asked if I'd garb up for him the next night. I agreed and told him to come by after work on Friday, but to generate me some clip to get ready.

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

"I think so. I get base about six, so come by my lieu around seven."

…………………………………………………………………………

The next day I really had some rue about agreeing to let him see me dressed up. I called him during luncheon and tried to game out, but he said I'd promised and he expected me to keep my promise. I was on border all good afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with odorous physical structure race, shaved my face, leg, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the thought of having this guy see me in my babe's clothes. I dried my tomentum and styled it girlish, then put on step-in, a bra, a nice dame, and a blouse, then sat down to do makeup. By now I had it almost to a science, putting on pedestal, then some accents, eyeliner, eye shadow, lipstick, and of course I painted my toenails and fingernails.

I wore some low hound with afford toes, to show off the toenail finish and looked at myself in the mirror. I knew I was a guy in drag, but I could hardly evidence when I looked in the mirror. I was still shaking and nervous when the buzzer rang at seven o'clock. My stifle were wobbly as I walked to the door. I looked through the peephole and sure plenty it was mat. I opened the door and let him in.

Matt was gaping and staring as he walked in my place. I closed and locked the room access and he turned me around then stepped back to take a good look at me. After looking at me a bit, he walked around behind me. He stroked my haircloth as he walked behind me, which made me anxious. He came back in front of me and grabbed me gently by the shoulders.

"Damn, that is hot, girl."

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

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

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

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

"I don't think we should do that, mat. I'm not one of your little lady friend, 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 tight and walked me over to the lounge, pulling me down beside him there. He had his arm around my shoulder and seemed to be getting way too lots delight out of this.

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

"Matt, this feeling 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 sexiest daughter I've seen in a while."

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

"Don't snap yourself down. nearly 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 modify into some normal dress, 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 someone sees me - recognizes me ?"

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

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

"No one but you and I will cognise, and besides I like a picayune 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 finger really weird."

"And maybe a piddling turned on ?"

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

"I do, and we should."

With that, Matt got up and take out me to my fundament. He wrapped his weapon around me and pulled me unaired. I think my eyes were the size of dish and my genu were getting decrepit 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 handbag, keys, and such ?"

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

"Grab one and your keys and let's go."

This was already getting way beyond anything I'd ever intended, and I was really afraid of where it was going to go. Matt went with me in the bedroom, and I went in the closet and found a bag that didn't flavor too bad with what I was wearing. I took my paint and wallet and dropped them in the bag before turning to Matt.

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

"Everything is going to be just all right, Lynn."

Matt actually had money, which is yet another understanding why most of the girls fell all over each early to get to him. We went downstairs to his brand new Amytal BMW Z4 convertible and he opened the door of the car for me. I managed to sit down in a somewhat ladylike mode - I don't think I showed too often. He got in and drove us to a very nice restaurant.

He used gentleman's gentleman parking and walked me in, holding the door for me. I still felt Wyrd as son of a bitch, but just tried to ignore how I looked and love myself. Matt ordered a prissy bottle of wine-colored for us, and I really needed something to drink. I downed my initiative glass before he'd taken More than a couple sips of his wine. mat poured me another glass, but I took it a little slower.

The server seemed very taken with me, and when he thought I didn't notice, tried looking down my blouse. various other men seemed to discover me, which made me squirm in my behind. One guy who works with Matt stopped at the tabular array to talk with us. I'd met him various multiplication before, but he clearly didn't distinguish me.

"Well, Matt, who is this beautiful madam with you tonight ?"

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

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

"And I'm very proud of to fulfil you, Lynn. mat is clearly a very lucky man. But if you want a change of scenery, feed me a call option, I'd beloved to show you a good time."

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

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

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

Oliver bent down and kissed my nerve before walking off.

"I do not fucking believe that."

"I tried telling you, Lynn. You are one hot skirt. Half the men in this space would dump their date for a probability to pack you home."

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

We had a lovely dinner party and I continued to drink way more than I should have. This unharmed conniption had blown my head so often 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 read 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 walk on the wild incline, just acquire a bit longer walk."

Matt wouldn't take ‘ no'for an solution and drove us to the spicy club in townsfolk. This was the sort of place that would never let the ilk of me inside. They must take in had a century people lined up waiting to get in. matt was obviously pretty well known, and he walked us up to the battlefront, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a potable and then Matt wanted to dance with me. I felt strange as tinker's dam, but it was a profligate figure and I was already one-half plastered so I went out to trip the light fantastic toe with him. We danced various fast saltation, then a slow phone number came on. I thought we'd go sit down, but instead, Matt pulled me close to him to dance.

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

My human knee got so faint that if he hadn't been holding me fuddled, I'd probably have slumped onto the floor. He gave me a long kiss, and to my surprise, I began to kiss him back. I felt run afoul - 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 mo before he walked me back and we had another boozing.

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

As I said, I'd been lustrelessness's wingman to a greater extent than a few times, and had seen him this way with women many clock time before. I also knew that in most pillow slip he ended up taking those fair sex abode 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 recognize how long we danced and drank, but by the time lustrelessness was ready to give, I was really plastered.

I thought matt was going to drive me back to my place, but instead he drove me to his apartment. As I said, matt had money, and he had a very nice two bedroom apartment - dainty furniture and all that. role of me hoped that he was going to let me barge in in the save bedroom. Another region of me wanted anything but that.

"matte, I really demand to get home and change."

"Lynn, dear, there's no hurry. Just relax and revel your walking on the wild side."

lusterlessness got us each a swallow, like I needed any more alcohol, and sat me down on the couch, sitting decently alongside me. lustrelessness 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 false boobs. 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 like it, and I told you I occasionally like kinky shit."

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

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

"What… What did you want me to do ?"

"If nix 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 pants with his early deal. He pulled out his cock, which was already hard and standing straight up. He kissed me again, then gently pushed my head down toward his motherfucker. I got close and looked at it. It was foresightful and voiceless and it twitched as I got near it. I decided I was not going to get away without doing something, so I took the psyche of his dick between my lips.

Matt moaned and leaned back, still keeping a hand on my head. I let the head of his cock faux pas from between my rim, before taking it back and going just a little farther with it. I bobbed up and down on his prick, gradually taking it deeply and deeper into my mouth. I'd never had a dick in my rima oris before and it felt unknown, but in another way, it felt very natural.

I slowly but steadily fucked his pecker with my back talk and Matt seemed to like it. Some precum came from the tip, and it had a salty gustatory modality, but I was so far gone I no longer cared. I could not get him all the way in without gagging, but stroked the base of his dick as I sucked the rest of it. By now, lusterlessness was moving his hips, almost fucking my oral cavity, as he held my head tight.

lustrelessness moaned loudly and got very inflexible as his cock erupted in my sassing. He held my read/write head with both hands as he emptied his balls into my throat. I swallowed his cum and gasped for breathing place, though it took a couple of swallows to get it all down. It gradually eased and I cleaned his dick off as I pulled my pass 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 sass as we kissed, but that didn't seem to nettle him. Matt continued to osculate me and I didn't even earn it as he pulled my annulus up over my ass and began to fondle my ass through my pantie. He even snuck his bridge player into my panties and fondled my bare ass.

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

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

"Do it, lustrelessness. Do it."

matt set me down on his bed on my hands and knees and pulled down my panty. My cock, which had been ignored for so longsighted sprang to attending, but matte was interest in other things. He took off his pants and shirt and got in bed behind me. He reached into a drawer in the table beside the bed and got a tube of lube.

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

I felt the head of his peter at my asshole and tensed for just a second before relaxing. At this point, I think I wanted him as much as he wanted me. I felt the head word get just inside me and I sighed and moved my ass back, getting to a greater extent of him in me. It hurt a bit, but matt took it easy and retard at low gear, until I really started to get into it.

I soon felt his articulatio coxae 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 paradise. I felt his tool slide oceanic abyss in me and fill me up. It turned me on in ways I'd never have expected.

matt slid his cock in me so far, I could almost sense him jab my venter. I'd almost swear I saw my tummy bump as he got all the way in. In nastiness of whatever reservations I'd had, I was loving every second of this, every stroke of his hammer. I wanted his peter 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 slope, with his tool still inside me. I was on a sexual high gear and wanted nothing more than to keep feeling his cock in my ass. His gumshoe was getting softer, but I wanted to keep him in me as long as I could. As we came off our gamy, matte began to stroke my shoulders and osculate the spine and side of my neck.

"Lynn, baby, you are beautiful, aphrodisiac, and howling, and I just wish I could ride out inside you forever."

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

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

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

……………………………………………………………………………..

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

Matt woke up and began stroking me and kissing the back of my neck opening as he eased around so his incision was up against my bunghole. I could feel it and wanted it back inside me. I reached around, grabbed his cock and guided it into my ass, as we lay on our slope. It was a gentler fucking, instead of the pounding that we had at the end last night, but I still loved it.

My pecker got unvoiced as I felt his filling me up. It was a slowly 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 much I enjoyed having this guy have sex me, but I knew I wanted it to go along as long as he wanted me.

"Lynn, sister, thank you for cobbler's last Night, and for this morn too."

"I hope we'll have more than just conclusion Nox and this morning."

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

"I want it. I want your pecker in my ass, in my mouth, wherever you want, and whenever you want."

"I want Lynn. I don't want Lenny."

"I never thought I would, but for you, I'll be Lynn."

"What happens to Lenny ?"

"Lenny has a job, and I don't think they'd appreciate Lynn showing up in place of Lenny. I need to be Lenny at work."

By then, Matt's putz had slipped out of my ass and I'd rolled over face up lusterlessness. I kissed Matt, and he kissed me back and began stroking my organic structure. We spent a foresightful prison term kissing and touching each other before we got up and went to the shower together. Without my apparel, my bra, my panties, I looked more like Lenny, but we washed each other, continuing to kiss.

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

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

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

Matt took me out again Sabbatum night, and took me back to his place. We were not as tired or drunkard and after I went down on him, he fucked me three metre. I enjoyed it but as I drifted off to kip, I was starting to find run afoul. Was this really how I wanted to inhabit out my life ? And how long was Matt likely to be interest in me ?

We fucked a pair more times the next sunup and I went home plate. I decided that Lynn would only be on Friday and Saturday night. I was going to live and ferment as Lenny, the rest of the meter. It was hard. We all want to be appreciated. We all want someone to think we are exceptional. Lenny is n't particular to anyone, though Lynn is.

Occasionally during the hebdomad, I would be Lenny and go out as Matt 's wingman. mat always found an attractive woman to use up dwelling. I was a small jealous - both of lusterlessness and of the woman. On uncommon occasions, I 'd be Lynn during the week, and matt would come to my place to hump me. Usually Lynn was a weekend thing, but some weekends, matt had former plans.

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

One Friday night, matte and I were at a club and I was being Lynn, though Matt seemed to be giving nearly of his attention to a very pretty blonde. I sat there feeling pretty neglected, when Nicole came up to speak to me. Nicole was a brunette, about my age, a bit taller, but with a very overnice shape, b-cup boobs, 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 dump you like that. By the way, my name 's Nicole. ``

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

'' well, your guy appears to be about ready to abuse out with another woman. Would you suffer any pastime in doing the same ? Or are you strictly into guy rope ? ``

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

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

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

Nicole reached up, and stroked my face. I 'd shaved as cleanly as I could before going out with flatness, and my facial hair is not thick, but there was the slightest hint of very light stubble and I could distinguish by her expression that she felt it. Nicole leaned forward and kissed me.

'' Well, Lynn, something tells me that you straddle the melodic phrase. ``

'' And you like that ? ``

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

'' I like women, I 'm just ... ''

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

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

At the end of the saltation, Nicole gave me a kiss that almost buckled my knees. I could sense my cock getting harder and barely being restrained by my step-in. My mind was blown. We stood there kissing for I'm not even sure how long. I'd never had a cleaning woman kiss me like that before, and I was in no haste 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 Saami time, it didn't bother me that much. I wasn't sure that I wanted a long term family relationship with flatness, and he seemed to still be pretty practically sleeping around. Besides, now Nicole seemed to be interested in me, or at least I hoped she was.

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

"Well, I guess I don't mind, 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 company. She worked near where I did and made some decently money. I was still amazed that she had any interest in the likes of me.

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

"I know your coming into court belies what you have down below, but I'm right with that. As long as you like girlfriend, I think we can have some fun."

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

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

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

Matt had left me and gone off. I could either call an Uber or detect out what Nicole had in mind. Honestly it was probably good than what Matt had done, even though I seemed to relish fucking Matt. I sat for several seconds, just pondering the possibilities. I looked at Nicole who sat there with a slight enigmatic smile on her nerve, then I leaned forward and kissed her.

"I take it that's a ‘ yes ’, then."

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

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the nightspot. She had a car nearby, nothing as expensive or loud as Matt's BMW, but a Nissan 370Z a match of years old. It was certainly nicer than my eight year old Civic. Nicole opened the car door for me, which surprised me a bit. Yes, Matt had been doing the same, but Nicole was a woman and knew what I was down below.

I stood slightly puzzled for a irregular before smiling at her and sitting down in a ladylike fashion. Before she closed the car door, Nicole leaned over and kissed me. She came around, sat down in the number one wood's derriere and started the car. Before she put it in gear, she smiled at me again and gave me a agile kiss.

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

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

"Better than your little boyfriend ?"

"No question."

We were stopped, getting prepare to exit the parking lot. I leaned over and gave Nicole a osculation. She smiled and stroked my head teacher, before taking us out on the route. She drove us a few miles to her apartment. It was on the arcsecond base and we had to walk a flight of stair, but we had our arms around each other, giggling and petting each other as we went.

Nicole had a squeamish little one bedroom place, clearly feminine, with a muted floral sofa and chairs, along with some art print on the bulwark. The prints were largely of charwoman and men, along with a few where it wasn't quite discharge if it was male person or female. She walked me over and we sat on the sofa, and she put her arm around me.

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

"I really just started dressing up in my sis's clothes as a turn-on. I told Matt one clock time when I was wino 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 clock time I go out this way is with him."

"But you were into guys ?"

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

"Have you been with any former bozo than him ?"

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

"fountainhead, I like Lynn, and I might even wish Lenny. How do you feel 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 fourth dimension ?"

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

"What about your small young man Matt ?"

"I think he's getting a little wear 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 belated tonight or tomorrow morning."

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the tenacious time. I wanted Sir Thomas More of trend, but I didn't want to cannonball along things and discompose her and maybe make her send me on my way. Nicole stroked my trunk, mostly back, arms, and ass, so I followed her lead and did the same to her. After a recollective stretch of kissing and touching, Nicole stopped.

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

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

Nicole took one of my men and placed it on her breast over her bra. I think my eyes must stimulate gotten very astray. She smiled, then leaned forward and kissed me as I held her boob. I wasn't sure where she was setting demarcation, but I couldn't helper but rub her booby through her bra. Nicole moaned and continued to kiss me.

My bra, of grade, 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 tremble of pleasure through my dead body. She had both hands on what would have been my tit, if I had any, so I placed my former hired hand on her early breast.

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

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

Her boobs felt amazing, warmly, soft, and just so wondrous. I began to caress her boobs and nipples as Nicole played with my chest. After a little spell, she stopped kissing me and guided my mouth down to one of her delicious booby. 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 kiss 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 titty seemed to make happy in my attention. After a bit, she shifted my point over to the other boob, and I began to turn over it the Saame attending that I'd been giving its partner.

I spent a long time kissing and pleasing her breasts, 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 institutionalise me on my way. Instead Nicole stood and pulled me to my feet and led me by the script into her bedchamber. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, sister, unzip my skirt."

I unzipped her and she let the dame slide down her physical structure onto the storey. She stepped out of the chick, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet spot in the front of them, as Nicole unzipped my annulus. My panties were having trouble restraining my prick, which had gotten very hard. She brushed lightly over it before lying back on the bed and pulling me down with her.

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

"Anything you want, Nicole."

"First, subscribe to off my panties."

I moved down her consistence and Nicole lifted her rosehip off the bed. I slid her panties down and once they were clear of her ass, she dropped her hips back to the bed and lifted her invertebrate foot, letting me take them completely off her. Nicole spread her legs and for the first metre I got to see a woman's slit. Nicole had shaved most of it, except for a minute funnies just above her labia. Nicole gently pulled my head to her nether regions, though I had no melodic theme what I was supposed to do.

"Okay, infant. Kiss it, lick it, stick that lingua in me."

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

I was still in replete makeup as Lynn, even if I basically looked like Lenny from the cervix down. As she pulled my panties off, she kissed the headway of my asshole, which was as hard as I've ever seen it. spirit, I'm no bang-up trill in that department, but I've got about six inch, and it was in its full-of-the-moon glory as Nicole slid back up my body.

I could finger my prick, sawing between her thigh, even rubbing across her pussy lips as Nicole writhed around on me. Finally, she lifted her hips, grabbed my shit and guided it into her sugariness cunt. She was so wet it slid in easily and very quickly I felt her hips up against mine as I was deep inside her. Once in, she paused a bit, getting us both used to the feeling of me being in her.

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

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

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

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

"I'm going to cum, Nicole."

"Do it baby, right wing inside me. Fill me up with it."

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

"We don't want you to escape 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 shoulder strap. She came back over to the bed and strapped it on herself, so it now appeared that she had a dick. She had me get on hand and knees, then got some lubricator from a nearby draftsman, before lubing up the penis and my ass.

Nicole eased the thing into my ass, until I was comfortable with it, then began to slowly fuck my ass with this strap-on. I wasn't sure I wanted her to do that, but at this point, I wasn't going to reason with her. As she began fucking me, I began to get into it. For obvious reasons, she was able to celebrate going a lot tenacious than matte even could, and my cock got hard again, and I came on the bed.

With that, she stopped and eased it out of my ass, then turned me over and kissed me some more. She kept the gimmick on her even through that. We kissed for a yearn time before she turned me on my side and spooned me, with her strap-on pressure up against my ass. We fell asleep that way and I had the most content eternal sleep that I've had in ages.

………………………………………………………………………………..

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

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

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

"That sounds large. 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 trouble 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 clothes back on. All I had was Lynn apparel, so I wore those and did my physical composition before I left. I got back to my apartment and sat on the sofa, just amazed at the last 24 time of day. While I sat there, my speech sound rang - a margin call from Matt.

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

"That was Nicole. We were enjoying ourselves."

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

"Actually, she took me back to her post, 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 make for with."

"You're hotter than Toni."

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

"semen on, little girl. If it weren't for me, you'd have had no sex life-time and no opportunity at that Nicole."

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

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

"She's all girl, but she's got devices. I'm not missing out on anything, and I'm getting things I could never get with you. I get to play with knocker, I get to bonk a pussy."

"Are you fucking dumping me, bitch ?"

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

"Lynn, how long do you suppose 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 former many women who fall all over themselves to be with you."

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

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

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

"And you've baffle requital for that. And if or when Nicole dumps me, if you aren't too big a squawk, you might even get more. In the meantime, I hope you have a gravid 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 adult female than to be with Matt.

I guessed I was epicene enough to get off on what I did with Matt, but why give up on womanhood if I had any hazard with them ? I was still sitting there in clothes as Lynn, when there was a roast on the door. 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 position me immediately, but turned to fill up and put away the door. She saw me and her sassing hung open and she seemed quick-frozen in place until she began moving slowly toward me. Karen got over to me, reached out a handwriting and touched my face.

"Lenny ? What the fuck ?"

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

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

"You're obviously in my clothes."

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

"Are you wearing my panties and bras too ?"

"I am."

"I got a freehanded shoes and was going to pick up the rest of my clothes, but if you've been wearing them, I don't think I want them anymore."

"I'm sorry. I'll pay you back, or buy you Sir Thomas More stuff."

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

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

"A girl ? A real daughter ? Not some in between or fake thing ?"

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

"Could be high-risk. You could be dressing like that and fucking guys."

I looked at my shoes. I couldn't feel Karen in the typeface. She understood immediately.

"roll in the hay. 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 detect another charwoman, you'll go back to fucking guys ?"

"Karen, please."

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

I was crying by this sentence. Karen made me ashamed of what I'd done and what I'd become. At the same metre, I needed make out too, and if being Lynn was what kept Nicole then I was going to preserve to be Lynn. I wept on Karen's shoulder, and she took some pity on me and stroked my head word and tried to soothe me. It took a spell before I regained my composure.

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

"I hope you can understand and forgive me."

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

"You were always popular with the guy rope. I could never get any of the little girl to give me a second look."

"So you dressed this way to get Guy ?"

"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 miss you're with now ?"

"Saw me, liked me, and figured out what I was. She liked women and men and seemed well-chosen 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 cognize how farsighted it'll last, but I'll do what I have to do to keep it going."

"Should I still call you Lenny ?"

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

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

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