It started kind of strange. I am or at least was Len or Lenny - Leonard to my female parent - a guy in my other 20s, kind of brusque and slender. I had a sister, Karen who was a few years former than me. She'd had a smutty detachment with a fiancé, and stayed with me for a while when she was trying to put her life back together.

It was a bit inconvenient, since I just had a one bedroom place, and not all that big. Being a Nice little brother, I let her have the bed, while I slept on the sofa. She had a ton of wearing apparel and more than filled my closet, leaving fiddling elbow room for my clothes. Beyond that, we had to percentage one tiny bathroom, in slip, since there was no way we were going to be in there at the same fourth dimension - too small and too weird.

Karen stayed with me for about six month before getting her own place and moving out. Her place was smaller than mine, so while she took nigh of her stuff, she had more clothes than she had elbow room for in the new topographic point. She didn't want to donate them, so she asked if she could result them at my blank space until she could afford a handsome place. Again, being a decent brother, I let her do it.

Karenic left behind all manner of things, skirt, attire, blouses, bras, scanty, shoes, physical composition, and all that. After I while I got fascinated with it, which I guess was my first misapprehension. 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 dress while touching myself, then jerking off until I came. I progressed to smelling the clothes and draping some of them over my headway while doing myself. After a metre, 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 bigger turn-on and her dress seemed to fit, since we were almost the same size.

As time went on, I'd clip 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 petty bit and even began to use some of the composition she'd left behind. I'd pad her bras with wind sock or whatever, put on panties, a skirt, blouse, and brake shoe, then brush my hair in a Thomas More feminine style and learned how to do my makeup.

It all seemed barren. I was in my shoes, by myself, using it all as part of self-stimulation. Hell, I needed to get off too, and there were no missy willing to help me. Before recollective, I'd come home from employment, dress up all girly, and swagger around my apartment before getting myself off. I'd even wear one of Karen's old nighties to bed afterward.

I had a few ally who I'd hang out with occasionally. One of them, who I'd known since high school was matte. He was always the popular sort, never had any problem getting girl, and often seemed to give birth one or more than hanging off him. He'd have me along as a wingman sometimes, though I never managed to get any lady friend 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 populace in a restaurant. He said they'd also gone to a movie theater, sat way in vertebral column, and she hiked up her skirt, sat on his lap, and fucked him in the theater during the movie.

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

"Shit, flatness, I can't get miss to do ordinary damn with me, much less anything kinky."

"come on, guy, you must have done something just a minuscule bit out there."

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

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

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

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

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

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

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

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

That was Thursday, and it was already late and I was too salute and had to work the next day. He asked if I'd dress up for him the next night. I agreed and told him to come by after work on Fri, but to give me some sentence to get ready.

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

"I think so. I get habitation 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 gage out, but he said I'd promised and he expected me to keep my hope. I was on sharpness all afternoon. I got home about six and took off all my clothes. I swear I was shaking as I cleaned up, showered with perfume body wash drawing, shaved my fount, legs, underarms, and body.

I almost felt like I was going to cry, I was so humiliated at the thinking of having this guy see me in my babe's clothes. I dried my hair and styled it girlish, then put on scanty, a bra, a skillful wench, and a blouse, then sat down to do war paint. By now I had it almost to a skill, putting on al-Qaida, then some accent, eyeliner, eye fantasm, lipstick, and of grade I painted my toenails and fingernails.

I wore some low cad with open toes, to present off the toenail gloss and looked at myself in the mirror. I knew I was a guy in pull, but I could hardly tell when I looked in the mirror. I was still shaking and nervous when the doorbell rang at seven o'clock. My knees were wobbly as I walked to the doorway. I looked through the spyhole and sure enough it was Matt. I opened the doorway and let him in.

Matt was gaping and staring as he walked in my situation. I closed and locked the door and he turned me around then stepped back to contract a good look at me. After looking at me a bit, he walked around behind me. He stroked my hair as he walked behind me, which made me aflutter. 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 employment. How about I call you Lynn ?"

"OK, Matt, you got to see me, now let me switch back."

"postponement 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, flatness. I'm not one of your short girlfriends, I'm Lenny."

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

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

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

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

"Matt, this look 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 aphrodisiac girls I've seen in a while."

"You've got plenty of daughter - tangible young lady, not fake ace, like me."

"Don't shoot yourself down. Most of those girls have nothing on you."

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

"Let me take you out to dinner, Lynn"

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

"No, babe, just like this."

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

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

"What if soul sees me - recognizes me ?"

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

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

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

"I don't know."

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

"That makes me feel really weird."

"And maybe a picayune turned on ?"

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

"I do, and we should."

With that, matte got up and drew me to my metrical unit. He wrapped his arms around me and pulled me close. I think my center were the size of disk and my stifle were getting weak as he leaned forward and kissed me on the impertinence. He let go with one arm and walked me to the room access. When we got there, he stopped and turned.

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

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

"Grab one and your key fruit 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. matte went with me in the bedroom, and I went in the W.C. and found a bag that didn't tone too bad with what I was wearing. I took my key fruit and pocketbook and dropped them in the purse before turning to Matt.

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

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

Matt actually had money, which is yet another reason why most of the fille fell all over each former to get to him. We went downstairs to his make new blue BMW Z4 convertible and he opened the threshold of the car for me. I managed to sit down in a somewhat ladylike fashion - I don't think I showed too much. He got in and beat back us to a very nice restaurant.

He used valet parking and walked me in, holding the door for me. I still felt Wyrd as diddly, but just tried to ignore how I looked and love myself. Matt ordered a squeamish bottle of wine-coloured for us, and I really needed something to drink. I downed my first glass before he'd taken more than than a duet 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 observance, tried looking down my blouse. Several other men seemed to notice me, which made me squirm in my behind. One guy who works with Matt stopped at the table to utter with us. I'd met him respective times before, but he clearly didn't discern me.

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

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

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

"And I'm very pleased to forgather you, Lynn. Matt is clearly a very prosperous man. But if you want a change of scenery, gift me a call, I'd love to show up you a unspoiled time."

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

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

"Well, matt, if you get tired of Lynn here, palpate free to transport 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 plaza 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 drink way more than I should have. This unit panorama had blown my head so much I didn't know what else to do. A few other men stopped to talk to us. They invariably seemed to pay inordinate attention to me, when they stopped to talk to Matt. We finished dinner party and I thought Matt would acquire me back to my place.

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

"Are you sure about that ?"

"You're taking a walk on the fantastic side of meat, just take a bit longer walk."

flatness wouldn't take ‘ no'for an answer and motor us to the spicy clubhouse in townsfolk. This was the sort of place that would never let the ilk of me inside. They must hold had a hundred people lined up waiting to get in. matt was obviously pretty well known, and he walked us up to the front line, and we were waved in, though I noticed he slipped the guy some money.

We went in and got a drunkenness and then Matt wanted to dance with me. I felt foreign as shit, but it was a fast number and I was already half plastered so I went out to dance with him. We danced various fast terpsichore, then a slow act came on. I thought we'd go sit down, but instead, matte pulled me conclude to him to dance.

He had one hand on my amphetamine back, holding me tight, as his early hand came down on my ass. He began to fondle my ass, which made me squirm. I could feel that mat had a hard-on as he did that. That scared me Sir Thomas More than a small, but I wasn't sure what I could do. I felt helpless as we danced. When the turn ended, matt stopped, held me besotted, and kissed me.

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

I'd been drinking pretty good before, but I didn't slow down. I was half afraid of what was going to take place, and felt like I needed to be very drunk. We drank more and danced 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 adult female, yet he was acting like I was the real thing.

As I said, I'd been flatness's wingman more than a few times, and had seen him this way with women many meter before. I also knew that in well-nigh pillowcase he ended up taking those cleaning woman home and fucking them. That scared me, but also seemed to turn me on, and it scared me that I was turned on by it. I don't know how hanker we danced and drank, but by the time matte was cook to leave, I was really plastered.

I thought Matt was going to push back 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 - nice furniture and all that. persona of me hoped that he was going to let me ram in the spare bedroom. Another component of me wanted anything but that.

"mat, I really postulate to get home and change."

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

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

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

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

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

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

"What… What did you need me to do ?"

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

"You want me to… ?"

"Please, Lynn, baby."

matt kissed me and stroked my ass as he unzipped his pants with his other hand. He pulled out his prick, which was already firmly and standing straight up. He kissed me again, then gently pushed my capitulum down toward his prick. I got finis and looked at it. It was long 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 head of his dick between my lips.

flatness moaned and leaned back, still keeping a hand on my drumhead. I let the headspring of his peter gaffe from between my lips, before taking it back and going just a little farther with it. I bobbed up and down on his slit, gradually taking it inscrutable and deeper into my oral cavity. I'd never had a tool in my rima oris before and it felt strange, but in another way, it felt very natural.

I slowly but steadily fucked his dick with my mouth and Matt seemed to like it. Some precum came from the tip, and it had a salty discernment, 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, flatness was moving his rose hip, almost fucking my sassing, as he held my head tight.

mat moaned loudly and got very rigid as his cock erupted in my mouthpiece. He held my head with both hands as he emptied his testis into my throat. I swallowed his cum and gasped for breathing space, though it took a duo of swallows to get it all down. It gradually eased and I cleaned his gumshoe off as I pulled my head back from it.

Matt pulled me up on him and began to kiss me some more. I know he had to taste his own cum in my rima oris as we kissed, but that didn't seem to inconvenience him. Matt continued to osculate me and I didn't even understand it as he pulled my skirt up over my ass and began to caress my ass through my panties. He even snuck his hired man into my pantie and fondled my bare ass.

I don't know why I didn't notice, I don't know why I didn't stop him. Maybe I was enjoying it all too much, and maybe I was just too toast. 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, babe. You are wonderful and beautiful, and I love what we've done, but I need to fuck you."

"Do it, lustrelessness. Do it."

matte set me down on his bed on my hands and knees and pulled down my scanty. My cock, which had been ignored for so longsighted sprang to attention, but mat was interested in other things. He took off his knickers and shirt and got in bed behind me. He reached into a drawer in the board beside the bed and got a tube of lube.

Matt rubbed lubricant 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 motivate it pretty freely after a min or two. He snuck a second digit in and began to feel make love my ass, and in nastiness of myself, I began to bang him back. mat leaned down and kissed the back of my cervix as he pulled his fingers out of my ass.

I felt the capitulum of his turncock at my dickhead and tensed for just a mo before relaxing. At this point, 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 Sir Thomas More of him in me. It hurt a bit, but Matt took it slowly and slow at first, until I really started to get into it.

I soon felt his hips slapping up against my ass as he fucked me. If you had told me beforehand that I'd enjoy having a guy ass my ass, I'd have thought you were unbalanced and told you to leave me the sleep with alone. Now Matt was fucking me and I was in promised land. I felt his stopcock lantern slide deep in me and fill me up. It turned me on in ways I'd never have expected.

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

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

"Lynn, baby, you are beautiful, sexy, and marvellous, and I just wish I could last out inside you forever."

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

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

Essentially, matte 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 a good deal of him in me for as long as I could, as we drifted off to sleep.

……………………………………………………………………………..

I woke the next break of the day with Matt still spooning me and with his strong 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 receive 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 spinal column of my neck as he eased around so his prick was up against my bunghole. I could finger it and wanted it back inside me. I reached around, grabbed his stopcock and guided it into my ass, as we lay on our side. It was a gentler fucking, instead of the pounding that we had at the end final night, but I still loved it.

My dick got hard as I felt his filling me up. It was a decelerate leisurely piece of ass, almost loving, and I reached behind me to stroke Matt's consistence 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 make out me, but I knew I wanted it to continue as long as he wanted me.

"Lynn, baby, thank you for last dark, and for this morning too."

"I hope we'll have to a greater extent than just last dark and this morning."

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

"I want it. I want your dick in my ass, in my sass, 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 prick had slipped out of my ass and I'd rolled over facing lustrelessness. I kissed Matt, and he kissed me back and began stroking my body. We spent a long time kissing and touching each early before we got up and went to the shower together. Without my clothes, my bra, my pantie, I looked more like Lenny, but we washed each early, continuing to kiss.

After we washed off his prick, I got down on my knees and sucked him off again. With my makeup off and hair wet, I didn't feel quite the Saame, but I dried my hairsbreadth, styled it as best I could and got dressed in my apparel from last night. I had a little makeup in my handbag and could do lipstick, eyeliner and a piddling al-Qa'ida, to make me more like Lynn.

The more I looked like Lynn, the Thomas More Matt seemed to be affectionate. He fucked me once more before taking me dwelling house, and we made a appointment for that eventide.

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

Matt took me out again Saturday nighttime, 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 times. I enjoyed it but as I drifted off to slumber, I was starting to feel contravene. Was this really how I wanted to endure out my life ? And how long was matte probably to be concern in me ?

We fucked a couple more times the next morning and I went rest home. I decided that Lynn would only be on Fri and Sabbatum nights. I was going to live and work as Lenny, the rest of the time. It was hard. We all want to be appreciated. We all want individual to think we are limited. Lenny is n't special to anyone, though Lynn is.

Occasionally during the week, I would be Lenny and go out as flatness 's wingman. mat always found an attractive woman to take dwelling house. I was a little jealous - both of matte and of the char. On rare occasions, I 'd be Lynn during the week, and matt would number to my topographic point to fuck me. Usually Lynn was a weekend thing, but some weekends, lustrelessness had other plans.

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

One Friday Nox, mat and I were at a club and I was being Lynn, though mat 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 nice cast, b-cup breast, and a pretty face.

'' fountainhead, 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 flatness and I have sort of an unusual relationship. ``

'' wellspring, your guy appears to be about prepare to step out with another woman. Would you have any interest in doing the Sami ? Or are you strictly into guys ? ``

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

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

'' What do you have in mind by straddling the line of reasoning, Nicole ? ``

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

'' Well, Lynn, something Tell me that you straddle the contrast. ``

'' And you like that ? ``

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

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

Nicole took my hand and led me out onto the dance floor. I glanced back at flatness and he was so fixated on the blonde that he never even noticed that I left. We did a distich of degenerate saltation, and I really enjoyed dancing with Nicole. nether region, as Lenny, I had trouble getting charwoman to even dance a lot with me.

A slow numeral came on and Nicole grabbed me and pulled me end. She put one mitt in the heart of my spinal column and the other one down over my ass. I giggled and squirmed as she caressed my ass through the dance. I glanced around and no one seemed to even mark us or what we were doing.

At the end of the dancing, Nicole gave me a kiss that almost buckled my knees. I could feel my dick getting harder and barely being restrained by my scanty. My head was blown. We stood there kissing for I'm not even sure how long. I'd never had a charwoman kiss 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 time, it didn't bother me that lots. I wasn't sure that I wanted a long full term relationship with lusterlessness, and he seemed to still be pretty practically sleeping around. Besides, now Nicole seemed to be interest in me, or at least I hoped she was.

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

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

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

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

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

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

"I like girls, I just never had a great deal hazard before."

"So maybe you never met the right hand girl before. As long as you're opened minded and flexible, I think we can have set of fun."

I felt a little unsure. Nicole was pretty and she seemed willing. I just didn't understand why she'd have any involvement in me - not after knowing that I was a guy dressed as a girlfriend who'd been out with a guy. Look, I'd never had any woman uncoerced to give me the time of day, much less get intimate with me. Nicole figured out what I really was and still seemed matter to. Now that was kinky.

flatness had left me and gone off. I could either call an Uber or encounter out what Nicole had in mind. Honestly it was probably skillful than what lustrelessness had done, even though I seemed to enjoy fucking Matt. I sat for various seconds, just pondering the possibilities. I looked at Nicole who sat there with a footling enigmatical grinning 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 waste side anyhow, why not walk a slight farther ?"

"That's my girl."

Nicole kissed me, then wrapped an arm around me and we walked out of the club. She had a car nearby, nothing as expensive or flashy as lustrelessness'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 second before smiling at her and sitting down in a ladylike fashion. Before she closed the car threshold, Nicole leaned over and kissed me. She came around, sat down in the driver's seat and started the car. Before she put it in gear, she smiled at me again and gave me a quickly kiss.

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

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

"wagerer than your little boyfriend ?"

"No question."

We were stopped, getting ready to pop off 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 Admiralty mile to her flat. It was on the indorsement floor and we had to walk a trajectory of stairs, but we had our blazon around each other, giggling and petting each other as we went.

Nicole had a overnice little one bedroom place, clearly feminine, with a hushed floral sofa and hot seat, along with some art prints on the walls. The mark were largely of adult female and men, along with a few where it wasn't quite sort out if it was virile or female. She walked me over and we sat on the couch, and she put her arm around me.

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

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

"Obviously, you did."

"He liked the way I looked and wanted to train 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 wire ?"

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

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

"Never. Most of the metre, I'm Len or Lenny, and I never look at or reckon about guys."

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

"I'd lovemaking that, Nicole."

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

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

"What about your little boyfriend Matt ?"

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

"What if he isn't ?"

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

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

With that, Nicole began kissing me. I kissed her back enthusiastically. We sat kissing for the longest time. I wanted more of course, but I didn't want to rush thing and upset her and maybe make believe her send me on my way. Nicole stroked my soundbox, mostly back, implements of war, and ass, so I followed her lede and did the same to her. After a long stretch of kissing and touching, Nicole stopped.

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

I was more than happy to do so, though my hired hand were shaking as I began to undo the buttons. As I did, Nicole began to unbutton my blouse. Her blouse was tucked into her skirt, and she asked me to draw out it loose and take it off her. She sat there with only her bra on the pep pill half of her body. I hardly even noticed as she took my blouse off me.

Nicole took one of my hands and placed it on her breast over her bra. I think my centre must suffer gotten very wide. She smiled, then leaned forward and kissed me as I held her boob. I wasn't sure where she was setting limitation, but I couldn't help but rub her boob through her bra. Nicole moaned and continued to buss me.

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

I was a little concerned about pushing it too far, but Nicole seemed to get even more turned on. We continued like this for a piece before she asked me to unhook her bra. I had been fastening and unfastening the 1 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 capitulation 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 kiss for a spell before she leaned back to give up our bras to descend off each of us.

My bra and padding fell to the floor, leaving my bare breast out there. I got my first off aspect at Nicole's boob - actually the start boob I'd ever seen survive and in person. I wanted to touch them but I was hesitant. I didn't want to travel too fast and spoil things. Again Nicole put my helping hand on one of her titty, then began to stroke my flat, boobless, chest.

Her boobs felt amazing, warm, mild, and just so rattling. I began to caress her boobs and tit as Nicole played with my chest. After a minuscule spell, she stopped kissing me and guided my backtalk down to one of her delicious boobs. I looked up at her, and she smiled at me, so I moved forward and kissed the white meat 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 breast seemed to revel in my attention. After a bit, she shifted my head over to the other dope, and I began to give it the Same attention that I'd been giving its partner.

I spent a prospicient metre kissing and pleasing her boob, before Nicole clutched my foreland 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 institutionalize me on my way. Instead Nicole stood and pulled me to my groundwork and led me by the hand into her bedroom. She walked us over to beside the bed then stopped and kissed me again.

"Lynn, sister, unzip my skirt."

I unzipped her and she let the skirt slide down her body onto the story. She stepped out of the skirt, then kicked off her shoes. She now wore only panties, and I could see a decidedly wet spot in the nominal head of them, as Nicole unzipped my skirt. My panties were having fuss 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 delight me first. OK ?"

"Anything you want, Nicole."

"start, rent off my panties."

I moved down her dead body and Nicole lifted her rose hip off the bed. I slid her pantie down and once they were clear of her ass, she dropped her hips back to the bed and lifted her feet, letting me take them completely off her. Nicole spread her legs and for the first clock time I got to see a cleaning lady's snatch. Nicole had shaved to the highest degree of it, except for a narrow strip just above her labia. Nicole gently pulled my straits to her nether part, though I had no idea what I was supposed to do.

"okay, sister. buss it, lick it, stick that lingua in me."

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

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

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

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

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

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

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

"I'm going to cum, Nicole."

"Do it cosset, rightfulness inside me. fill up me up with it."

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

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

"That was wonderful. 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 phallus, 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 handwriting and knees, then got some lube from a nearby drawer, before lubing up the penis and my ass.

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

With that, she stopped and eased it out of my ass, then turned me over and kissed me some more. She kept the gimmick on her even through that. We kissed for a long time before she turned me on my side and spooned me, with her strap-on pressing up against my ass. We fell asleep that way and I had the most content 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 pussy. We showered together, playing as we washed each other. I went down on her in the shower and she went down on me after.

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

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

"That sounds great. I've got some errands and matter to do this afternoon, so you need to get your cute trivial ass home plate, and I'll see Lynn back here at seven."

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

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

"Not as long as I can spend my meter with you."

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

I put my apparel back on. All I had was Lynn dress, so I wore those and did my war paint before I left. I got back to my flat and sat on the sofa, just amazed at the finale 24 hours. While I sat there, my speech sound rang - a call from Matt.

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

"That was Nicole. We were enjoying ourselves."

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

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

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

"Yeah, she was."

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

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

"You're raging than Toni."

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

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

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

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

"She's all fille, 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 make love a pussy."

"Are you fucking dumping me, squawk ?"

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

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

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

"I give it two workweek at the outside."

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

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

"Just think back, if you out me as a hybridisation dresser, you also out yourself as fucking a guy who cross dresses. 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 aim payment for that. And if or when Nicole dumps me, if you aren't too big a bitch, you might even get to a greater extent. In the meantime, I hope you have a large 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 difference was that I got more out of it with Nicole. It wasn't just me being fucked, I got a hazard to get mine too. Fact is, given a choice, I'd rather be with Nicole or some former woman than to be with Matt.

I guessed I was bisexual enough to get off on what I did with matt, but why give up on char if I had any opportunity with them ? I was still sitting there in clothes as Lynn, when there was a knock on the door. I was puzzled, because I wasn't expecting Nicole, flatness, 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 Karenic came in the apartment. She didn't spot me immediately, but turned to close and lock the door. She saw me and her sassing hung loose and she seemed fixed in piazza until she began moving slowly toward me. Karenic got over to me, reached out a hand and touched my face.

"Lenny ? What the screw ?"

"Karen, I'm not quite for sure 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 form of a long story."

"Are you wearing my step-in and bras too ?"

"I am."

"I got a bigger place and was going to pick up the sleep 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 to a greater extent stuff."

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

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

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

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

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

I looked at my skid. I couldn't feel Karen in the face. She understood immediately.

"screw. 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 observe another woman, you'll go back to fucking Guy ?"

"Karenic, please."

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

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

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

"I hope you can realize 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 cable. I could never get any of the girl to cave in me a second look."

"So you dressed this way to get guys ?"

"I just dressed like this to get myself off, until a guy I knew saw me. He liked what he saw, and while I wasn't completely well-heeled, 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 happy with me dressed like this."

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

"I don't know how yearn it'll last, but I'll do what I have to do to stay fresh it going."

"Should I still squall you Lenny ?"

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

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

Karen left, and I went in the bathroom to fix my makeup and then changed clothes. I'm not sure where the relationship with Nicole will take me, but I guess metre will tell .