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Kyle The Crossdresser
🕑 Added 2022-05-08 00:00:57 +0000 UTCI am Kyle, a 26 year old professional. I'm 5'11" and 170 pounds and reasonably fit. I don't claim to be any sort of Adonis, but have not had problems attracting women. I shared a 2 bedroom apartment with Quinn, about the same age but about 5'6" and 135 pounds. He was slight though not really effeminate and worked remotely a lot.
Quinn never seemed to have much luck with the women and spent a lot of time at the apartment, unless I took him along to be my wingman. As I've said, I did pretty well with the women, but he never managed to snag one. He seemed to be depressed about it a lot, and a few times I tried to fix him up with someone but it never seemed to work out.
We were sitting at the apartment early one Friday evening, drinking beer and talking. Quinn was depressed, as usual, and seemed to be down on women, mostly because he had so little luck with them.
"Girls have it so damned easy. All they have to do is sit back and wait for the guys to pursue them."
"It's a little harder than that. There's doing makeup, hair, clothing, then flirting to catch the attention of the right guy."
"Still, it seems like most girls who want a guy can find one."
"That's easy to say when you have no idea what it's like to be a woman."
"It's not like I'm going to be able to find out."
"What if you could find out?"
"You think dressing in drag is going to teach me what's it's like to be a girl?"
"No, I mean really being a woman for a little while."
"That's not possible. Sex change is irreversible and takes a long time."
"What if there were another way?"
"Something that would let me really be a girl and change back?"
"Exactly."
"How the fuck could that happen?"
"A magic ring. When you put it on, you become a woman. When you take it off, you change back."
"You're bullshitting me."
I walked in my room, dug in a drawer and found the ring. I walked back out holding it in the palm of my hand. I walked over to Quinn and held out my hand with the ring in it. He looked at my hand then looked me in the face, then looked back at my hand.
"I still don't believe you."
"Try it and see."
"Maybe you should try it first."
"Been there, done that, don't need to do it again."
"I still don't believe you."
"But you're not brave enough to put the ring on and prove me wrong."
With that. Quinn snatched the ring out of my hand and slipped it on his finger. All at once, he had a shocked look on his face and sat back in his chair. He grunted and groaned and made weird faces as changes rippled through his body. He leaned back and panted as his body began to change. It took about ten or fifteen minutes, at the end of which, Quinn the guy was now Quinn the woman.
"Oh, fuck."
Quinn's voice was higher. She now had c-cup breasts and a feminine face along with softer skin, wider hips, and a narrower waist - and no Adam's apple. Quinn looked down and saw her boobs, and tentatively touched them. She slid a hand down between her legs and found no penis. She looked up at me in shock.
"That really changed me."
"No shit."
"And I'll change back when I take the ring off."
"There are things you have to do in order to be able to take the ring off."
"What do you mean?"
Quinn starts tugging at the ring, which will not budge from her finger. She has a frightened look on her pretty little face as she looks back at me.
"You didn't tell me there were conditions for taking the ring off and changing back."
"You grabbed the ring and jammed it on before I could tell you."
"What the fuck do I have to do to get it off again?"
"First, it stays on for a minimum of a week."
"A week? I have to stay this way for an entire fucking week?"
"Then you have to have a female orgasm."
"I suppose I could masturbate to get that."
"And you have to have a man cum in your pussy."
I thought Quinn was going to have a heart attack. Her face turned almost purple between some combination of anger, fear, and embarrassment. She began to gasp for air and clutched her chest, which reminded her that she now had boobs. She looked down at her boobs, then looked up at me with horror in her eyes.
"I have to let a guy fuck me and cum in my cunt?"
"You do indeed."
"You said you did this>"
"I did."
"And you let a guy fuck you?"
"It's amazing what it will teach you about women."
"I don't know if I want to do that."
"You don't know if you want the chance to change back to a man?"
"I don't know if I can do that."
"It's not that hard. Like I said, I've done that. It was actually rather pleasurable, but I prefer being a man fucking women."
"Shit."
"Look, you're going to be this way for a week, so we need to get you some panties, bras, and jeans that fit better."
"I'd rather just wear my clothes."
"They're not going to fit as well, and you need some support for those nice boobs."
Quinn put her hand in front of her chest to cover her breasts. Her tee shirt, which now fit more snugly made it clear that her nipples had gotten quite hard. In spite of her protestations, Quinn was getting turned on by all of this. She turned red, and squirmed in her seat. I thought I could see just the slightest hint of wetness in the crotch of her jeans.
"I wish I had never done this."
"Just enjoy the ride while it lasts. Besides, we need to do something with that hair."
"What's wrong with my hair?"
"If you're a guy who doesn't care about his appearance, nothing. If you're a woman, everything."
"Oh shit."
"Let's do some shopping - my treat."
"No skirts, no dresses - understand?"
"Spoil sport."
"Fuck you."
"Maybe later."
"Fuck, no."
"You're gonna have to fuck someone."
"There's no other way?"
"Nope."
"Shit. I'll have to think about this. I screwed myself."
"And now you get to be screwed by someone else."
"That I'm used to - just not literally."
"Let's go shopping. Enjoy this experience while it lasts. Embrace it."
"There's a difference between embracing this and embracing some guy and having him shove a dick in me."
"That can be quite pleasant, once you let go of your hang-ups."
I drove her to a discount store, where I bought her several pair of panties and a couple of bras to start. She didn't want anything pink or lacy, or even remotely sexy. Need I even bother to mention that thongs were a no-go. I did manage to steer her toward bikini panties, though all in solid colors and mostly dark. She went for black and dark blue, but put the kibosh on some red panties.
She wanted to just wear her boy jeans, but I got her to try on some nice women's jeans. She almost freaked the first time she went in the women's dressing room. I found her some jeans that fit her ass nicely, and as a women, she had quite a nice ass. I picked out a couple of tops that looked cute and seemed to fit. Again, we had to stick with neutral colors - nothing too girly.
I took her back to the apartment, and with a little pressure managed to get her to shave her armpits and her legs, though she did protest a bunch. I even got her to trim her bush with a beard trimmer, though she refused to shave that. I had her put on some if her new clothes, then spent a few minutes trying to get her hair to look a little more feminine.
I took her to a salon and they trimmed her hair and styled it in a much cuter fashion. Quinn was shocked at how she looked and even if she didn't want to be too girly, still seemed pleased at the result. She was beginning to look like a really pretty woman. I don't know if she began to accept it so much as she seemed to get numb over all the changes.
I took advantage of that to get her to a nail salon, where I had them trim and clean up her nails nicely and put a fairly muted color on them. She was pretty antsy about that, but again, was shocked by how cute it made her look. I dragged her to a department store where I had them do her makeup and buy some items. Even numb, she whined a bit over wearing makeup, but when they finished, she was gorgeous.
"Keep in mind, all this is temporary. At the end of a week, you can donate the clothes and ditch the makeup, and go back to brushing your hair in a masculine fashion."
"I can't believe how I look, but still,,,"
She was going to rebel when I took her to get her ears pierced. I had to tell her that after her female week, she could ditch the earrings and the holes would close back up and no one would ever know. Besides, some straight guys wear earrings now. I just bought her two pair of earrings and the person told her how to take care of her ears while it all healed.
Quinn now looked every bit a woman, and frankly was something of a knockout. She wanted to head back to the apartment, but I persuaded her to let me take her to dinner. I put my hand on her lower back as we walked in which made her squirm a bit, then I pulled out her chair when she sat down. She really was kind of freaked by it all, but I ordered a bottle of wine and she quickly drank up.
As Quinn drank, she seemed to loosen up and began to play with it all a bit. We had a male waiter and she flirted with him and even held my hand for a while. I don't think she accepted it so much as just quit trying to fight it for a while. By the time we were done eating, Quinn was not feeling any pain. I drove us back to the apartment.
She insisted that she wanted to jill herself to a female orgasm, rather than letting me bring her there. She went in her room and locked the door, not that an interior lock would keep me out, but I figured it was better to let her feel comfortable with the whole thing. I sat watching cable when she came out half an hour later with her clothes somewhat askew.
"I tried, and I can't make myself cum."
"I know you aren't too thrilled with the idea, but I can try to see if I can get you to cum."
"You're absolutely sure I have to cum as part of what it takes to change back?"
"Yeah, and I did that when I wore the ring and changed."
"I feel weird about having you see me naked like this."
"If I'm going to make you cum, not only will I see all that, I'm going to have to touch it - a lot."
"I hate it, but let's do it."
We went into her room together, and when she stopped, I began to first stroke her back, then I leaned forward and kissed her neck. She whimpered and pulled away.
"I don't want you kissing me."
"I won't kiss your lips, unless you kiss me, but I need to kiss other parts of your body."
"So I guess I'm going to get a lesson on what you do to your girlfriends."
"Most of them really seem to enjoy it."
"I've heard some moans and shrieks before. Made it hard to sleep sometimes."
"So let me show you how I please them."
I took her hand and led her over to the bed. I could see her bite her lip and tremble as we went. I sat her down on the bed and sat beside her. As I stroked her back, I could tell she had removed her bra. I kissed her neck as I put my hands on her waist, then moved my hands up her sides. I held off on touching her boobs. A lot of women don't like you to go for their breasts too quickly, and she was antsier than most.
Her tee shirt was not tucked into her jeans, so I snuck my hands under her tee and actually stroked her skin, still sticking mostly to her sides. She gasped as I touched her skin and squirmed nervously. I caressed her bare back, under her top, while continuing to kiss around her neck and up onto her ears. She moaned and squirmed as I did, but didn't pull away.
I stuck with that for a while, until I could feel her begin to relax, then I snuck a hand around and lightly grazed the very edge of her left breast. When she didn't protest that too much, I did the same with the other hand and the other boob. I could tell she was starting to get into it, in spite of her reluctance. I fondled a little more of the breast while easing her tee up over her boobs altogether.
I paused and lifted up on the shirt, and she raised her arms and I pulled it off her. She looked apprehensive as I began to kiss her upper chest and moved my hands up her body until they were on both her breasts. I took it a little slow, but before long was running my thumbs over her nipples, which were rock hard.
"Shit. It never felt that good when I touched them."
"I think I've spent more time touching women's boobs than you have."
"Mine were the first I ever touched."
"You're a virgin?"
"Please don't tell anyone."
"That I took my male roommate's virginity - no chance of that."
"I'm not a male right now."
"You certainly aren't."
"I'm really embarrassed."
"How does a guy get to be 24 years old and still be a virgin?"
"I'm kind of shy, and none of the girls ever seemed much interested in me."
"I'll make you a deal."
"What's that?"
"You have to have sex with a guy to change back."
"I wish I didn't, but..."
"And you have to be a woman for a week."
"Whether I like it or not."
"Let me make love to you all this week, while you're a woman, then when you change back to a guy, I'll help you find a woman that you can lose your male virginity with."
"All this week?"
"Gives you a chance to see what sex is like from the female side. It's not like you'll get that chance again. Embrace it while it's here."
"And you'll help me when I change back?"
"Absolutely. And I know just the woman to do it."
"You're sure you can find a woman that I can lose my virginity with?"
"If I can't find someone within two weeks, I'll put on the ring and become a woman and let you fuck me."
"Okay, then."
With that, I leaned forward and kissed her nipple. She gasped and grabbed my head. She didn't pull me away so I kept kissing and licking that boob, as Quinn began to moan. I pushed her back to lie on the bed, then got up and swung her legs over so she was completely on the bed. I crawled onto the bed beside her and resumed making love to her boobs.
She was basically a c-cup with very nicely shaped boobs. Then again, what had she done to make them droop? She had dark areolas that were just begging for attention, and nipples that were stiff and calling out to me. I sucked on one nipple like I was trying to suck it off her. I nipped it lightly with my teeth, which caused her to gasp and moan.
As my mouth teased that boob, I stroked the other one with my hand. I could feel her squirming under me as I pleasured her breasts. She moaned and stroked my head. I switched to suck on the other boob as I fondled the first one. I like women's boobs and I like to enjoy them and do my damnedest to make sure the woman enjoys what I'm doing as well.
Her moans almost sounded like she was weeping, but she kept my head to her chest, so it was pretty clear she didn't want me to stop. She began to rock back and forth as I kissed and sucked her titties. She had what almost seemed like some sort of spasm, before she slumped back on the bed and let go of me. When she did, I began to kiss my way down from her breasts to her pussy.
Quinn almost seemed to be out of it, until I began to lick her pussy in earnest. Her legs, which had been lying limply on the bed , were quickly wrapped around my shoulders pulling me closer to her. As I continued to lick her, I eased a finger into her pussy. By now she was soaking wet down there and it slid in easily. Her clit began to peek out at the top of her cunt, and I gave it a lick.
She began to move her hips, and it felt more like she was fucking my face than like I was tongue fucking her. She lifted her ass off the bed, using her legs around my shoulders as leverage, and jammed her sweet snatch into my face. Look, I've gone down on some women, but I'd never had any woman who seemed to enjoy that as much as Quinn did.
I was happy making love to her snatch with my tongue and my fingers. I don't know how long I was down there, but I think she came twice, just from that. Finally, her legs gave out and flopped limply to each side releasing me from my willing bondage. Once she did, I kissed my way back up her body, spending a little more time with her breasts as I did.
I didn't kiss her on the lips, since I still wasn't sure she welcomed that. I positioned myself over her and snuck the head of my cock between her pussy lips. She was a virgin still as a female, and had an intact hymen, so I eased my way in until I hit that barrier, then backed out to where I was just barely in her. I repeated that a few times until I eased my way in and she thrust her hips getting me past that and deeper in her.
I was only about halfway in, but wanted to take it slow and make it as pleasurable as possible. I eased out and back in several more times, getting slightly deeper with every thrust, until I was all the way in and felt my hips tight against her. I paused for a few seconds to let her get used to the feel of having a prick filling her up.
Once I felt she was ready, I started slowly, pulling nearly out before plunging deeply in her again. As she seemed to get into it, I gradually picked up speed and power until I was fucking her cunt both hard and fast. She seemed to enjoy it and was fucking me back as I took her on her maiden voyage into womanhood.
Honestly, five to ten minutes is pretty normal for me, but I wanted this to last and think I managed to stretch it out to fifteen minutes or more before I could tell I was going over the edge. I jammed my cock as deep into her as I possibly could and filled that pussy with my cum. As I did, Quinn seemed to awaken and grabbed my face and began to kiss me almost as though her life depended on it.
We kissed as my balls emptied themselves in her sweet love canal. We kissed until my dick softened to the point where it began to slip out of her. I could feel her push her hips forward, trying to keep me inside her as long as possible. She wrapped her legs around my hips holding me tight to her. Though I got softer, I didn't slip out for the longest time.
I know, some men have, or at least claim to have limitless sexual stamina. I knew I'd be able to get it up again before too terribly long, but I was going to need to recover a bit first. Finally, she let go of me and I rolled us over so she was now lying on top of me. That was nice as I could rub her ass and her boobs better that way than when I was on her.
Funny that not too terribly long ago, Quinn had not wanted me to kiss her and had only reluctantly agreed to sex. Now she was kissing me with great abandon and seemed quite enthusiastic about it all. That made me feel much better about the coming week and the prospects for sex during that time. She was attractive as a woman, and I was more than happy to fuck her. I was just sad to think that it might only be for one week.
We kissed and I continued to stroke her ass and fondle her boobs. Pretty soon, I started to get hard again. As I did I could feel my cock sawing around her perineum. Clearly, Quinn could feel that as well and she made very satisfied animal sounds as she squirmed around on me. Then she lifted her hips, reached down and grabbed my prick and guided it into her pussy.
She moved slowly and sensually as she began to fuck my cock, driving it deep into her being then nearly out again. We kissed as I played with a boob with one hand, and snuck my other hand around and put a finger in her ass. As I did, she gasped and got a little more hip movement into her fucking. She moaned and gradually picked up speed, though she still kept it slower than my fastest.
I had a few lovers in my time, but I don't think I'd ever been with anyone who seemed to enjoy sex as much as Quinn did. I could feel my cock bottom out in her pussy, as her hard nipples scratched my chest. She clearly had surrendered to the feeling and I did as well. I think I enjoyed fucking Quinn more than I had ever enjoyed fucking any other woman.
Her moans increased in volume and frequency and I suspected she was about to cum again. I was nearing that myself and tried to hold on until she came. She seemed to lose herself, frantically fucking me before collapsing on me and gasping. I turned loose and let myself go and filled her cunt with my cum.
She stopped kissing me as she recovered from her latest orgasm, just lying on me panting and sighing. Eventually she recovered enough to lift up a bit, look at me, and give me a somewhat cynical smile.
"I suppose the whole week is going to be like this."
"Would that be so bad?"
"At current rates, it might kill me."
"I'd never let that happen. Besides, we each have work, and have to sleep and eat some time."
"I suppose if I'm going to die, being fucked to death might be one of the better ways."
"I don't want you to die. I want to make love to you as long as you're a woman, and as long as you'll let me."
"I have to be a woman for a week. I don't have much choice about that."
"I'll do my damnedest to make it a good week for you."
"I can't say I ever wanted to be a woman, but you've made it better than I expected."
She relaxed on me, putting her head on my shoulder as my cock softened and eased its way out of her. I think we both dozed off, then awoke a bit later made love once more then we went to sleep with me spooning her and holding her breast. As we drifted off, she sighed and snuggled back against me. She wiggled her hips against my semi-erect cock as we both drifted off to sleep.
..............................
I was drifting awake in the morning, when Quinn seemed to awaken with a start. My dick was hard and pressing into her ass, as I spooned her and held a boob. She had a brief little half sob and her body was tense for a minute before she seemed to lose a little of that tension. She pulled away slightly, then turned over to face me. She looked concerned but not distraught.
"A week of being a woman, and a week of being fucked."
"I kind of got the impression you were getting into it last night."
"It felt okay, but I still feel weird about being fucked by a guy."
"It only felt okay? Damn, I'd like to see how you react to really great sex."
"So what are we doing today?"
"Would you like to shower together?"
She had kind of a nervous squirm, and while it was hard to tell under the covers, she seemed to be moving her hips. That seemed to cause her legs to move and had an effect on her pussy as well. She seemed to realize that and had kind of a surprised expression. She bit her lower lip and looked at me, though she kept her eyes somewhat lowered.
"Should we really do that?"
"You're a woman - at least for now - and I'm a man. Besides we made love several times last night."
"Seems to be upping the ante a bit, doesn't it?"
"I've already touched and kissed all of it."
"Yeah, but..."
"Look, when you take off the ring and are a guy again, you want to get somewhere with women. Right?"
"I'd like to."
"You need to know how to please a woman."
"But as a guy."
"As a woman, you can learn what makes a woman feel good."
"I suppose."
I took her hand and led her to the bathroom. We got in the shower and turned it on. She seemed reticent, but I had some nice floral body wash that I kept for women who stayed over. I took some of that and began to slowly, sweetly, and gently clean her body. As I washed her breasts and her ass and her pussy, she closed her eyes.
I leaned her against me and kissed her neck as I washed and rinsed her. Her nipples got hard and I spent far more time washing and rinsing them than was needed just to get them clean. She was breathing hard and moaning as I turned her toward me. My cock was hard and it sawed between her legs as I pulled her to me.
She lifted up on her toes and I slipped my dick into her tender little pussy. She gasped and opened her eyes, first in shock, then in pleasure. It was a little harder to get deep inside her, until she wrapped her arms around my neck then lifted and wrapped her legs around my waist. She began to fuck me, driving my prick deep into her snatch.
I leaned against the shower wall, as she impaled herself on me. While there was no doubt that I enjoyed it, I let her drive it all and before long, she was moaning as she reached her orgasm. I tried to hold off and once she started to cum, I let loose and as she settled down pulled her tight to fill her cunt with my cum.
I stood, holding her, with my slowly softening dick still in her pussy. After a minute or two, she opened her eyes, looked at me and smiled, then laughed a quick, short laugh. She kissed me, then unwrapped her legs from around me and stood up, still keeping her arms around my neck. She looked down and bit her lip, then looked back and kissed me again before giving a sexy wiggle and turning to rinse off in the water.
We touched a lot more as we finished washing and rinsing, then dried each other off. It was almost like she changed and was really letting herself be a woman, at least for a time. I've showered with a few women in my short happy life and she was as sexy and feminine as any of them ever were. I wasn't sure how long it would last but decided to make the most of it while I could.
I kissed her and patted her ass, and sent her off to dress, while I put on some clothes. I met her in the living room later. She had styled her hair and put on makeup, and while she might not have been as good as the professionals, she did a credible job of it. She had on a cute outfit and when she came into the room, she had a sexy walk.
"Since I have to be a woman for a week, and be your lover during that time, I might as well be the best woman I can."
"You're already beautiful and sexy."
She did a little curtsy when I said that, which really blew my mind. I could only hope that Quinn stayed this way though this week at the least. I found myself hoping that she would stay that way even longer. I suppose I am greedy. I've had some very pretty and sweet women as girlfriends in the past, though sadly none of those ever really worked out.
At any rate, we went to the mall. There was a moderately nice restaurant in the mall and we needed lunch, so we went there to eat. There was also a movie theatre there and I figured I could take her to see a movie - almost like a real date. She had a preference to see a chick flick that was playing, which in itself was something of a shock. As a guy, Quinn had never seemed interested in that sort of thing.
We had a while before the next showing, so we wandered the mall. She now seemed to have more interest in looking at women's clothes. She tried on a few items and modeled them for me, including a cute skirt, which I bought for her. As we wandered, we passed a Victoria's Secret, and she looked in there and bit her lip.
"I'd be happy to buy you something sexier, if you model it for me back at the apartment."
"You just want to see me parading around in sexy underwear."
"Quinn, I've seen you naked, made love to you, and showered with you."
"So you want me mostly undressed so you can finish undressing me and have your way with me."
"You already agreed we'd be lovers this week. I just want you to look sexier along the way."
"So let's see what they have."
We went in and started to look at some of the items. There were some floral lacy hip hugger panties that were on sale, so we selected a few different colors of those in her size. They had some lacy bras that were very cute and we selected a few of those as well. They had a cami and short set that were hot as hell, and we got one of those for her as well.
I was almost drooling at the thought of seeing her wearing some of those, not that I intended to keep her in them for very long. She seemed to get flirty as we shopped for the items. I was surprised, but also pleased. As long as she was willing to be a woman, I wanted to make full use of that. We finally finished our shopping and I bought the items for her.
We went to the movie and she wanted to sit near the back. She lifted the armrest between us and snuggled up close to me. I put my arm around her and she rested her head on my shoulder. We mostly just stayed that way for much of the movie, though it came to one particularly romantic part and she lifted her head, looked at me and opened her lips slightly. I leaned forward and kissed her and we kissed for a few minutes, until she pulled away.
"Much more of that and I think we'd be getting inappropriate in public."
"We are in back, which makes it harder for anyone to know."
"I think you'll get plenty of that in private - you already have, in fact."
"Not enough. You're one of the sexiest women I've ever been with."
"Wait till we get back to the flat."
She put her hand on my leg and ran it up and brushed very lightly over my cock. It's not nice to tease like that and I almost came just from that light brush. I put my hand on her leg and did much the same, brushing over her pussy. I wasn't quite as delicate as her and kept going rather longer, until I felt just a touch of dampness. She grabbed my hand and moved it away.
After the movie, we left the theatre with arms around each other. I found myself wondering what had happened to my male roommate. Now that she was a woman, she seemed to be completely submerged in womanhood. Not that I minded at all. As a woman, Quinn was sexy, and by no means did I want to think of her or behave towards her like she had ever been male.
We hung out for a while before we had a nice dinner. Then I suggested that we go dancing. We went to a club that I had been to a few times. Quinn obviously had no ID showing her as a female of drinking age. Somehow we suspected her male ID would not pass. I took it easy on the drinks as she had soda and a few sips of my drink when we could get away with it.
We mostly fast danced and enjoyed it, then a slow number came on. I took her in my arms and pulled her close and she molded herself to me. I could feel her boobs against my chest and I wanted her as bad as I have even wanted any woman. My prick was hard and she rubbed her body against it as we danced. I was afraid I was going to cum right there in the middle of the dance floor.
As the number ended, I looked at her and kissed her. I'm not sure how long we kissed. Time stood still and we were there blissfully unaware of anyone or anything but each other. When we broke the kiss, without a word, we both knew we wanted to go back to the apartment and revel in each other's bodies. I know I had the previous night and that morning, but wanted so much more, as did she.
We raced back and no more than closed and locked the door before we began to undress each other. She was in bra and panties and I was in boxers when I picked her up and carried her to the bed. She giggled and held me tight as I did. I set her on the bed and she spread her legs wide as I climbed onto the bed beside her.
We spent quite a while kissing before I slid down her body. I lifted lightly on her hips and she raised them from the bed and I pulled off her panties. She spread her legs wide again and I plunged my tongue into her sweet pussy. I reveled in her sweet musky aroma as I licked her. Her juices flowed freely as I licked her.
I enjoy going down on women and particularly enjoyed going down on Quinn, now that she was female. She seemed to be in heaven as I licked around her pussy, before plunging my tongue as far into her as I could get it. I'm not one of those with a super long tongue, but I used what I have to make her feel as good as I possibly could.
Her labia spread as I licked them and my mouth made love to her pussy. Before long, she was thrusting her hips and pushing her quim into my face. I loved it and licked her pussy until she screamed with pleasure. She had wrapped her legs around my shoulders and pulled me so tight into her that I could barely breathe.
Finally, she turned loose of me, and her legs flopped loosely to the side. I gave a few last licks to her pussy before kissing my way up to her breasts. I kissed, licked, sucked on, and nibbled them as she moaned and squirmed beneath me. She grabbed my head and pulled it away from her boobs, as she panted.
"Please, Kyle. No more. Just stick that dick in me and fuck me."
I couldn't possibly turn down that kind of request from a lady. She had her legs spread wide as I moved up and lined my cock up with her sweet little pussy. I eased the head just inside her and she pushed her hips forward to get it deeply in, then grabbed my head and began to kiss me. It almost felt she was trying to devour me as I slowly fucked her. We fucked, touched, and caressed for another hour or more before we passed out from exhaustion.
...............................
We spent a lot of our free time in bed, making love for the next week. I had to go into work several days, but could work remotely some of the time. Quinn was a contract worker who worked remotely most of the time. As we neared the end of the week, I began to despair. Quinn had been the best lover I'd ever had and I really wanted her to remain a woman and remain my lover. She had put on the ring early Friday evening, and the week would be up the next Friday.
"Quinn, I know your week is about up, and you will be able to take off the ring and change back to a guy."
"We had a deal, and you said you'd help me lose my male virginity after I changed back."
"Would you please hold off on taking the ring off and changing back until after the weekend?"
"You want to continue to fuck me for a few more days."
"I think I've made you feel good, and I'll do my best to make those few extra days as enjoyable as possible."
"Tell you what - I won't change back tonight, and we'll take it day by day after that."
"I'll do my best to make it as enjoyable as possible for you."
We made love through the weekend, and I was the best lover I could possibly be during that time. Monday morning, I had dressed and was getting ready to leave for work, when Quinn came in, still a woman, but with an odd expression.
"The ring won't come off."
"That's weird. We've done everything we need to do, and the week is up."
"Check and see what else might cause it not to come off."
Quinn was puzzled, but not distraught, which was a relief. A lot of people would be upset or angry, but she mercifully didn't seem to be. I had gotten the ring from a distant relative, and called them during the day, and told them about the situation. They gave me a couple of possibilities. I called Quinn and told her what I'd learned. I got home after work and Quinn sat in the living room.
"I'm pregnant. That's why it won't come off."
"So it won't come off until you've had the baby and weaned it."
"So I have another year and a half as a woman."
"I got you into this. I'll be here to support you all the way through this."
"I'm a contract worker. I don't have decent insurance to cover the costs."
I sat beside her on the sofa, took her in my arms and held her tight. I took a deep breath, because I knew what I suggested would be a major step.
"You're a woman, at least for the next eighteen months."
"I believe that's what I just said."
"I have company insurance. Let's get married. That will cover the maternity costs."
"And after eighteen months?"
"When you change back, we'll divorce and figure out how to handle the baby."
"So I'll be your wife and lover for the next eighteen months."
"Would that be so bad?"
"I expect you to treat me right."
"Haven't I done that so far?"
"No slacking off. No taking things for granted."
"I promise."
"Then I accept."
...................................
We married shortly after, and I had her put on my health insurance. We settled into living as a normal married couple. Quinn suffered through morning sickness and all the other consequences of pregnancy. She had the baby, a beautiful little girl, who we named April. Quinn breast fed April and seemed to dote on her.
Before April was weaned, Quinn was pregnant with another child. She said that two was going to be it, she would have no more, though by that time, she seemed to have decided she was going to remain a woman. I'm happy with what happened and love Quinn and April and want them to stay a part of my life.
I knew that pregnancy would make it impossible for Quinn to change back for quite some time, and I deliberately made love to her without protection, hoping that would happen. As a woman, Quinn was the best lover I'd ever had, and I found I genuinely did love her and wanted her to stay with me as a woman.
I knew she didn't have insurance that would cover the maternity, which would push her to marry me, at least for a time. I also had unprotected sex with her after she had April, hoping to get her pregnant again. I succeeded and am pleased that she has decided to stay a woman, and just hope she never changes her mind.
I lied to Quinn. While it was necessary for her to have sex as a woman to change back, it was never necessary for me to cum in her. I can't ever tell her that, as it would be a betrayal of trust. I don't think she'd leave me, but I don't want to chance that. I think from the beginning I wanted her to stay a woman and to stay with me.
How foolish of Kyle to think that I couldn't break the encryption on his postscript. I am at least as good a computer nerd as he is, and probably better.
So he lied to me, but he did so because he wanted me to stay with him as a woman. When I first changed, I was upset and certainly wanted to change back as soon as possible. Once we became lovers, I found I really enjoyed sex as a woman. Sure there is a lot of sexism out there, but working remotely, I am less in contact with it.
I found myself falling for Kyle and let him fuck me without protection, perhaps hoping that something like what happened would happen. I was concerned that he'd grow weary of me as his female lover and want to move on to another woman. I wanted to stay a woman, but only if I could have him as my lover for the long term.
At the end of one week, I checked and found the ring would come off, though I didn't take it all the way off. When he asked me to stay a woman a little longer for him, I was ecstatic, but didn't want to seem too eager. When I found I was pregnant after the extra time, I was pleased and just hoped that would make him 'do the right thing', and it did.
We're married, we're lovers, we have one child and another on the way. I can't say I enjoyed childbirth but I love April and love Kyle and will love our next child, who will be another girl. I never plan to take off that ring and plan to be married to Kyle for the rest of our lives.
Comments
Charley Lee
I loved this story. Thank you for sharing it.
