As I grew up, I knew I wasn’t a guy – not a normal guy anyhow. The normal boys liked doing rough things, fighting, playing war, playing sports, watching sports, hunting, fishing, all those male things. I didn’t like any of that. On the other hand, I never wanted to be thought of as a sissy. I went through some of that, so I hung out with the boys and did just enough boy things so no one bothered me.
I was always a bit shorter than the other boys, never as muscular. I always tried to move and act in a masculine manner, but as I grew, I ended up about 5’6” and about 140 pounds with rather a delicate frame. My face was not clearly feminine, kind of in between masculine and feminine. I never had all that much body or facial hair and got teased even as it was.
I looked at the girls and I envied them. They could do all kinds of fun things that I could never do. They got to dress up and be pretty, where I never could. When I got a little older, I stole a pair of panties and would wear them alone in my room, when I was sure no one could ever find out. I never went much beyond that when I lived at home. I was always scared of being found out and humiliated.
The first chance I got, I moved from home and got my own place well away from my relatives and my so-called friends. I worked full time and went to community college part time evenings and weekends. Once I had my own apartment, I began to experiment a little more. I started off by getting several pair of panties. I always wore them at home, never out anywhere. I was too scared that someone would know.
After a while, I’d take an occasional brief excursion out while wearing panties – never very long or very far from home. It just always felt so thrilling to do that, but I worried about someone finding out. After a while, I bought a bra, then two or three. I only ever wore those at home, and would fill them with socks or something to make it look like I really had boobs.
I never wore the bras out of the apartment. I just knew if I did that someone would know and would humiliate me, call me a sissy, or worse. Gradually I got a little more daring. I went to thrift stores and bought a few skirts, blouses, and dresses, along with nice shoes – flats at first, later heels. I never wore any of that out of the house.
I let my hair grow longer, but lots of guys did. I just made sure to keep it a boyish long, everywhere but in private. At night, in my apartment, when I knew no one would bother me, I had fun and dressed up. First it was just wearing the dresses, bras, and panties, then I took to shaving my legs and underarms. I never went to the gym, so I figured no one would ever know about that.
After a while, I even painted my toenails, and left them that way. On weekends, if I had no classes, I might paint my fingernails, but I always took that off before going to work on Monday. I even began to buy makeup and wear it when home alone. I didn’t date much. I liked girls, but was scared that they would find out about my dressing and be disgusted by it.
All this was at home. I never went outside my apartment in any of this. I was just too scared. I knew somehow someone would know I was a boy dressed up as a girl. I’d get beaten up or called a faggot, or maybe even killed, who knows. At any rate, I spent many evenings alone at my apartment dressed up the way I really felt comfortable.
I knew there were boys who went out that way. There were boys who were that way all the time. Some of them got hormones or even had surgery. I could never bring myself to do that. I just had my private quiet girl evenings and weekends, at least until the unexpected happened.
One Friday night, I was at my apartment in a very pretty skirt and top. I’d done my makeup and my nails and even styled my hair. I looked the way I felt, even if I didn’t dare let anyone see it. All of a sudden there was a loud, frantic knocking at my door. I knew there was no way I could answer the door the way I was dressed, so I stood frozen in place, until I heard a very plaintive voice from a young woman who lived nearby.
“Please help me. Let me in. Please.”
I was scared for myself, but I was also scared for her. She continued to knock, and plead for help, crying, even. I think it was the crying that got to me. I went to the door, unlocked it and opened it. Melissa rushed in closing the door behind her and locking it.
“Oh, God, thank you so much.”
There were tears running down her face and her makeup was a total mess. Her clothes were a mess as well. Then she turned and saw me.
“Oh. I didn’t… realize.”
She stopped crying and slowly walked over to me. She reached out and touched my face.
“Casey? You are Casey aren’t you?”
I started to cry and she looked distraught.
“Please don’t cry. I’m sorry. I never meant to…”
My knees were shaking and I was struggling to keep from crying, as Melissa gently took my arm and walked me over to the sofa. She sat down and sat me down next to her. She grabbed a tissue and wiped my tears, and her own, then stroked my face.
“Thank you for letting me in. You may have saved my life. I appreciate it and don’t want to do anything to hurt you. Please believe me.”
I was still scared and ashamed. I sat there trembling. Melissa leaned forward and gave me a very tender kiss.
“Casey, dear. I think you’re wonderful. And I don’t care how you dress.”
“You’re… just saying that.”
“No, baby, I’m not just saying that.”
With that, she pulled me close to her and gave me a long passionate kiss. At first I didn’t know how to react. I was almost scared to react. I’d never really kissed anyone, girl or boy. But as she kissed me, I began to kiss her back, tentatively at first, then more enthusiastically as we continued.
I felt like I was in heaven. Here was this cute girl, kissing me, even after she saw me dressed as a girl, even knowing I was really a boy.
Melissa was about 20, a brunette with hair just below the shoulders, about my height, 5’6”, but about 120 pounds with a pretty face, a nicely rounded shape and b-cup boobs. She had cute, sassy outfits when I saw her and always had a sweet smile. I had always been taken by her, I was just always afraid to do anything about it. Now circumstances had brought her to my apartment and my sofa.
After we kissed for a while, she stopped and looked at me, smiling.
“My face must look a wreck. Give me a minute to fix it, I promise to come back. Please wait here – the way you are.”
She clearly wanted me to stay dressed as I was. I nodded and she smiled and gave me a quick kiss then walked to my bathroom, looking back, smiling, and putting a little extra into her hips as she walked. Needless to say, I was stunned. Here was this cute girl, who saw me dressed and made up as a girl. Instead of running screaming from the apartment, she kissed me and wanted to be with me.
Melissa fixed her face and her clothes in the bathroom and came out after a few minutes and walked back to the sofa. I was still uncertain, which had to have shown on my face. She sat down, as close to me as she could get, gave me a quick kiss and put her arm around me. She leaned back on the sofa, pulling me close to her.
“Casey, honey, the way you dress doesn’t bother me. I like boys, I like girls, and I like boys who look like girls, and sometimes girls who look like boys.”
“What happened to you – that you were knocking at my door?”
“A guy I know got violent. He grabbed my spare key and he knows where I live. I got away from him, but was afraid if I went to my place he’d use the key and get in.”
“I was afraid to open the door, but you sounded desperate.”
Melissa kissed me.
“I was desperate, and I understand why you were afraid, but I’m glad you opened it.”
“What will you do now?”
“Tomorrow, I’ll have the manager change the locks, but I can’t go home tonight.”
“Where will you stay?”
“I was kind of hoping that you might let me stay here.”
“I… I only have one bed, but…”
“One bed works, and I don’t mind sharing it with you, if you don’t mind sharing it with me.”
“Casey, dear, do you like girls?”
“Have you ever been with a girl?”
I shook my head. I started to tear up again. Melissa smiled, leaned forward and kissed me again.
“Casey, do you like me?”
“You’re beautiful, Melissa.”
“If you’d like, I’d love to be your first girl.”
I sat there stunned, unable to speak. Melissa gave me a long passionate kiss that I returned as best I could. She stroked my face and my hair and pulled me close to her as we kissed. After a bit, she stopped, stood up and drew me to my feet. She put an arm around me and walked me to the bedroom. When we got to the bed, she pushed me down on it, then climbed on top of me.
“Just follow my lead, Casey, baby.”
Melissa spent a long time kissing and stroking me before rolling off.
“Casey, honey, since you look like a girl, you’re going to start off by pleasing me the way a girl would.”
“I don’t know what to do.”
“Unbutton my blouse.”
I was hesitant, but began unbuttoning her blouse from the top. I stopped at the bottom of her blouse which was tucked into her skirt.
“Unzip my skirt, honey. Then finish unbuttoning my top.”
I did and she sat up, allowing me to take her blouse off her. She kissed me, then took my left hand and put in on her right boob, over her bra. I gently squeezed her boob, reveling in how soft it felt. She wore a lacy black bra that showed just a hint of her nipples through the lace. I so wanted to see and touch what was under that lace.
“Unhook my bra, baby. I’m sure you can manage that.”
I had put my own bras on and taken them off enough that I was pretty familiar with them. But I felt nervous as I reached behind Melissa to unhook hers. She smiled at me as I eased it forward off her, and dropped in onto the floor. She lay back down taking both of my hands and putting them on her breasts. I’d never seen real breasts live and in person, much less touched them. I marveled at the feel and the look.
As I caressed her boobs, she moaned and closed her eyes, eventually pulling my head down to one tit.
“Kiss it, suck on it, baby.”
I kissed the nipple, making her moan and squirm. I kissed, licked, and sucked all around that breast. I didn’t know if I’d even get the chance to do this again, and I wanted to make the most of it while I could. Her nipples got very hard, and Melissa arched her back as I enjoyed her boob. After a bit, she had me more over to the other one, and I kissed and sucked on it while stroking the first one.
Melissa’s boobs might not be the largest, but I enjoyed every square inch of both of them. I kissed, licked, sucked, and stroked like there was no tomorrow. After a while, I could feel her arch her back again, and felt her stomach muscles rippling under me as she moaned and gasped and held my head. As it eased up, she pulled my head and I moved up her body to kiss her again.
“Well, Casey, baby, for someone who’s never been with a woman before, that wasn’t too bad. Time for the next course. Take off my skirt and panties.”
I slid down her body and she lifted her hips, which let me pull down her skirt and panties. She wore lacy black panties in a thong style that went well with her bra. Her panties were soaked and even her skirt was wet. She dropped her hips and lifted her feet so I could get them all the way off. After I did, Melissa spread her legs very wide.
She had just a narrow strip of hair above her pussy. Her pussy lips were wet and already spreading as she opened herself to me. She pulled my head down to her pussy. I marveled at it, but wasn’t quite sure what to do.
“Kiss it, baby. Lick it. Stick that tongue in me.”
I leaned forward, closing my mouth around her pussy. She moaned and thrust her hips forward. I stuck out my tongue and licked her pussy, bottom to top. Melissa had the most satisfied moan, and she moved her hips around. I stuck my tongue in her as I licked and sucked. I saw and felt a little button peeking out at the top of her pussy. I took it between my lips and sucked on it. Melissa arched her back so strongly she almost threw me off her.
“That’s great, Casey. Use your fingers too.”
As I licked her, I stuck a finger into her pussy.
“Deeper, baby, deeper.”
I pumped my finger in and out of her as I licked her and teased her clit. She was soaked and pumping her hips as I eased a second finger into her. I felt her cunt tighten around my fingers, as Melissa grabbed my head and held me tight against her. She had her second orgasm, then pulled me back up her body. We kissed again, with her juices still on my lips.
“Baby, you can be my girl any time. But now I guess it’s time for me to let you get some pleasure.”
Melissa took off my top. She stroked my faux boobs, as she kissed me, then she unzipped and removed my skirt. I was there in bra and panties, with my prick harder than I’d ever seen it in my life.
“I think there’s someone there who wants a little attention. We’ll take care of him in just a minute.”
Melissa kissed me and reached behind me to unhook my bra. I felt strangely naked as she pulled it off me, even though I had no boobs. She still reached down and stroked my nipples, which were amazingly sensitive. She then moved down to kiss both nipples, before lifting lightly on my hips. I raised my hips and Melissa pulled off my panties, freeing my cock.
“Baby, I’m going to drive this train.”
Melissa pushed me onto my back then ranged over me. She reached down to grab my dick as she kissed me again. I felt her slide the head of my prick across her pussy lips. I wanted in her so badly, but knew she’d get me there, after she teased a bit. After she rubbed the head up and down her cunt a few times, she slid the head just inside her. I was on the verge of that which I’d only ever dreamed of.
Melissa kissed me as she slowly lowered herself, taking my cock deep inside her. Once I was all the way in, I could feel her up tight against me. She paused and kissed me again.
“What do you think, baby? Does that feel like home? Does that feel like someplace you’d like to call home?”
“You are so wonderful. I love you.”
She began to fuck me, slowly at first, gradually picking up speed. As she did, I played with her ass with one hand while playing with a boob with the other hand and kissing her as much as I could. I was in heaven. I’d pleasured myself more than a few times, but never actually fucked a woman before. I didn’t want it to end.
I could feel my orgasm building up. I wanted desperately to cum inside her, but wasn’t sure if that’s what she wanted.
“Oh God, Melissa. I’m cumming.”
She impaled herself on my cock, getting it deep within her. I felt her cunt tighten around my prick as it twitched and started to spurt. It felt so good, I think I blacked out for a few seconds. I regained consciousness with Melissa kissing me ravenously. It felt like she was trying to devour me, and I was fine with that. They say the female praying mantis devours the male after sex. If that’s what was happening, I was totally on board with it. This ride was more than worth it.
“For someone who hasn’t been with a girl before, you did pretty good. That warrants an encore later on.”
I just lay there with my balls emptying themselves in Melissa’s sweet pussy, until it felt like there was nothing more left there. She kissed me and stroked me, and I kissed and caressed her.
“Well, babydoll, you’ve been my girlfriend and my boyfriend. Did you like it?”
“That was wonderful. You’re wonderful.”
“Is that something you think you’d like to do on a regular basis?”
“You mean you and me, together, again, a bunch? Hell, yes, I’d like that.”
“We might be able to do that if you can be a little open minded.”
“Open minded? How?”
“You’ll be my girlfriend, and you’ll be my boyfriend, both in private and out together.”
“Out together – as a girl? Are you sure?”
“So sometimes when we’re out you’ll be dressed as a boy, and sometimes as a girl.”
“You mean you want me – like in public?”
“Exactly. And sometimes I’ll be your girlfriend, and sometimes I’ll be your boyfriend.”
“I’ve never been out in public as a girl.”
“Work with me for a few weeks. If you decide you don’t like what we do, you can go back to being alone and dressing up all by yourself.”
“But if I’m willing?”
“I’ll open worlds to you that you’re only beginning to imagine.”
“Okay – I guess.”
Melissa kissed me and we spent quite a while kissing and touching. We turned onto our sides and she introduced me to 69ing. I ate her out again, tasting my cum leaking from her sweet little pussy as she sucked on my dick. I felt her do a first quick lick on the head of my prick, taking it between her lips, then letting it pop out.
She slowly took me deeper and deeper until I was all the way, with my cock down her throat, and her breath tickling the hair on my balls. Unlike when we fucked, this was slow and easy, until I gushed in her mouth and throat. She held me tight and deep as I shot my second load, then eased out, cleaning off my cock as she came. She came on my mouth. And we swung around and kissed. I could taste my cum on her lips as she tasted herself on mine.
After playing a bit more, we dropped off to sleep, with her spooning me. I could feel her up against my ass, as she reached around and grabbed what would have been a boob, if I had boobs. I still felt a delicious tingle as she played with my nipple.
We woke up the next morning with her still holding me. She turned me over and we spent a while kissing and touching each other.
“So baby, are you ready for your first day as the new Casey?”
“We’ll need to clean up and then go shopping.”
“I need to clean off this makeup and nail polish and put on some boy clothes.”
“No, baby. You’ll dress and make yourself up the way I saw you last night, and we’ll go out together.”
“I’ve never been out in front of other people dressed as a girl. Until last night, no one had even seen me that way.”
“And now it’s time for the new Casey. And sometimes the new Casey is going to be a girl when she goes out.”
“Do I have to?”
“Nope. I can walk out of here and never see you again, and you can keep it all private.”
“I want to be with you.”
“Then you need to do it on my terms. Today you’re my girl. Now let’s go shower and get dressed.”
That was the longest shower I’d even taken in my life, but it was also the most fun. We kissed and caressed as we soaped each other up and rinsed off. It finally culminated with fucking right there in the shower, which meant a little more cleaning off, but neither of us complained. I shaved my legs, underarms, and body hair, along with shaving my face. I’m not especially hairy anyhow, but it was better that way.
Her panties from last night were a bit of a mess, so she borrowed a pair from me. Her skirt was also a bit messy, but I had one that fit her okay. She picked out some sexy panties and bra for me, along with a pretty little skirt and blouse. Melissa helped me work on my hair and makeup. I was okay, but she really knew what she was doing, and when we finished, I looked better than I ever had before.
I looked in the mirror when we were done, and I knew I was a boy dressed as a girl, but it was hard to tell from looking, and Melissa kept telling me I looked great. I was nervous as hell, the first time I set foot outside my apartment dressed as a girl. She continued to tell me everything was fine and that I was her girl and it would all be okay.
We went to her place, and she dropped off her dirty clothes and did her makeup with her own colors, then we went by the management office, where she told them about the key problem and they promised to change the locks before the end of the day. They gave her a key for the new lock and she was happy.
While we were there, the manager gave me the occasional look. At first, I was worried that he recognized me, then he looked at me and licked his lips and smiled. I realized he’d been checking me out and I blushed furiously. As we finished, he smiled at me, even broader.
“Sweetie, you can come by and visit anytime.”
I giggled, blushed, and scooted out of the office, with Melissa right behind me. Once we were outside she grabbed me, hugged and kissed me.
“See, Casey baby. You already have a fan.”
“I – don’t think I’m ready for any male admirers.”
“Maybe down the road a bit.”
I must have looked very concerned. Melissa laughed, hugged and kissed me again, then took my hand and we went to her car. She drove us to a sex shop, which kind of concerned me, but she told me to relax and it would be okay.
Nobody seemed to pay much attention to us as we wandered around the shop. Melissa found some realistic breast forms, b-cup. That embarrassed me, but she told me we needed something better than socks crammed into my bra for boobs. She also got some kind of adhesive.
“What are you going to glue?
“We need to make sure your new boobs stay where they’re supposed to be.”
“You’re going to glue those boobs to me?”
“That’s what I just said.”
“How do I get them off? I can’t go to work that way.”
“There’s a solvent, and I’ll get some of that too. Relax, baby.”
She took me over to another area, where they has some very pretty panties, but with a special pocket in them. I was puzzled about that.
“Baby, we need to keep your thingy properly hidden away when you’re a girl.”
“I don’t know if I can afford all this.”
“It’s my present to you for being such a good girl for me.”
She got several pair in my size, all very sexy. I was really embarrassed when she took me up to pay for them. There was a female clerk, who looked me up and down before ringing up the purchases. She then gave me a very sweet smile. She then turned to Melissa.
“She’s very nice. Let me know if you get tired of her.”
I blushed, giggled, and squirmed, and I swear I almost wet my panties right there in the store. Melissa turned and gave me a long kiss before turning back to the clerk.
“I think I’ll keep her for now.”
Melissa took me back home to put on our new purchases before we did anything else. She had me take off my blouse and bra, then threw the socks I’d used to stuff it, back into the corner. She put adhesive on the boobs and carefully placed them on my chest, then had me hold them in place while the glue dried.
I let go and they felt like I had real boobs on my chest, and the color was close enough that it was hard to tell they weren’t really me.
“Now, baby, isn’t that better than having some crummy socks filling out your bra?”
I nodded and she kissed me. When we were sure everything was perfectly dry, I put my bra back on and was amazed at how it looked and felt. When I walked, they looked like real boobs moving, under my clothes.
She had me take off my skirt and panties, then threw the panties aside. I put on one pair of the new ones, with a little help from Melissa, and when we were done, it was almost impossible to tell there was a prick in there, even without a skirt on. I put my skirt back on, and looked more like a girl than before.
“So, is my best girl ready to go get some lunch?’
We went to the mall, to the food court to a little Thai place and got some food. We sat out in the food court eating our lunch. Before long, we had a couple of guys sit down nearby and try to chat us up. They were both about six feet tall, nicely muscled, and it was weird but looking at them made me squirm in my seat.
“So what are you two lovely ladies doing this afternoon?”
“We’re just a couple of girls out shopping. That’s all.”
“Would you like a little company for your shopping trip?”
“Thanks, but I’m afraid our boyfriends wouldn’t appreciate it.”
“I promise we wouldn’t tell them.”
“I’m terrible at hiding things from my boyfriend. He’d take one look at me, and he’d know. Thanks, but we’ll pass on your generous offer.”
“That’s a shame. My friend and I would really like to get to know you both a lot better.”
“Our boyfriends are both very jealous.”
“Some other time, maybe.”
“Maybe someday, but not today.”
They eventually gave up. We finished our meal and left. We wandered the mall a bit, not buying anything, but doing a lot of window shopping. Where I’d been very nervous about going out in public, by the time we’d spent a couple hours at the mall, I felt very natural going around as a girl. We seemed to have lots of guys checking us out, and a few others hit up on us, but Melissa sent them all on their way.
“See, Casey, baby. You had nothing to worry about. Now don’t you feel silly about being afraid to come out in public?”
“Yeah, but look at the guys trying to pick us up. And if some of those knew what I have between my legs, some of them would be real pissed.”
Melissa kissed me.
“Baby, that’s why we’re not going to tell or show those guys. And I’m not sure I’m ready to share you anyhow.”
That night, we went out for a few drinks. I was still a little apprehensive, because guys in bars sometimes want to buy you drinks and then think it entitles them to something more. Instead, Melissa took me to a gay bar. The guys there had little interest in me, though there were some women who seemed interested in both Melissa and me.
There was one woman who expressed interest in a threesome, and two others who wanted to do kind of a tag team thing between the four of us. Melissa gently discouraged them. We drank and danced and generally had a pretty good time. I’d never realized quite what I’d been missing sitting at home alone. Being out with Melissa was wonderful.
We went back to her place tonight. Since the locks were changed, we felt pretty safe, and were, as it turned out. I went down on her again, which we both enjoyed. She seemed to enjoy playing with my boobs, even if they were fake. The weird thing was it turned me on too. After she came, she told me it was time to further my education.
Melissa got down on all fours and had me fuck her doggie style. She had to guide my dick into her pussy, but it felt great. The angle made it feel much different from fucking her normal style. I took it very slow, easing in and out of her, as I first grabbed her hips to steady myself and steady her as well. Then I reached forward and grabbed her boob with one hand as I held her hips with the other.
Melissa moaned and fucked me back as hard as I fucked her. Not much more than 24 hours earlier, I’d never been with a woman and now I had a beautiful lover who was truly opening new worlds for me. She moved her hips around as well as back and forth, which turned me on even more. I plunged deep into her to fill her pussy with my cum, collapsing onto her back as I did.
I rolled off her and we spent a while kissing and fondling each other, before Melissa stopped. She got up and went to the bathroom. When she came out she was wearing a strap-on. I was puzzled and concerned as hell about that. She came over and lay besides me, stroking my face and kissing me.
“Baby, I told you, you could be my girl and my boy, and that I’d be your girl and your boy. It’s time for the next step.”
I was scared and didn’t really like the idea, but I also didn’t want to lose Melissa and everything else we were doing. She had me get down on all fours, with my head buried in a pillow. I figured I knew what she was going to do. I didn’t want to, but also didn’t want to tell her no.
She opened a drawer beside the bed and got out some lube. She lubed up the strap-on, then took some lube on her finger and eased her finger into my ass. At first I didn’t like the feel, and my ass was so tight, she had trouble getting the finger in.
“Relax, baby. We’ll take it slow and easy, so we don’t hurt you.”
I tried to relax and gradually her finger got deeper in me. She finger fucked my ass with that finger and after a few minutes, it felt pretty good. She eased a second finger into me, which took a few more minutes to stretch me out so it was comfortable. Before long, I was moving my ass around as she pumped me with her fingers.
She added a third finger, and once I relaxed a bit, I no longer cared. She was fucking my ass with her fingers and I was happy with it. She pulled her fingers out and put the head of the strap-on at my asshole. I tightened down a bit, but she had stretched and lubed me so the head started to ease into my ass.
She eased back and forth and I could feel the thing slowly get deeper and deeper into my ass, sometimes half an inch at a time, sometimes a little more. After several minutes of this, I could feel her hips against my ass and realized she had the thing deep inside me. I also realized that my dick was hard again.
I didn’t understand why my dick would be hard because Melissa was fucking my ass, but it was, and as she fucked me it seemed to hit spots that turned me on more than I’d ever have suspected. I know she had no nerve endings in that thing, but she was really getting into fucking my ass, and I was enjoying it as well.
I fucked her back as hard as she fucked me and before long, I came right on the bed, gasping as her strap-on filled my ass. She waited until I recovered before pulling out of me, then rolled me over and kissed me.
“Well baby, for someone who didn’t seem to want that, you seemed to really get into it.”
I could feel a buzz in my ass as it tightened down and got used to being empty again. I squirmed a bit and kissed her.
“It felt good, but I’m not sure – “
“It’s only one piece of the whole package. But it’s all or none, baby.”
“For you, I’ll do that – at least for now.”
“That’s my girl.”
We fucked a bit more before going to sleep with her spooning me again.
We woke up Sunday morning and made love again before showering. Melissa dressed and we went to my place, where she had me dress again as a girl. I mean, I often spent my weekends dressed as a girl, but always only by myself at home. Now I was being a girl in public, all weekend.
At Melissa’s suggestion, I moved in with her and we began sharing the rent, which was a financial benefit to both of us. At her request, I began wearing panties to work, since no one could ever see them anyhow. On weekends, I had fingernails polished, but not for work. Since I wore socks and shoes, I left the toenail polish on even when I went to work. The panties and toenails made me feel sexy, even though only Melissa and I knew.
One weekend afternoon, we went to a bar in the area. We had a few drinks and danced, before we had a couple of guys decide they were more interested in us than in the football game on the television nearby. I was antsy, but Melissa said they could buy us a drink. They asked for a dance, and Melissa said okay and told me I should dance with the one guy as she danced with the other.
It was a fast dance for a couple of dances. I started out pretty uptight, but after a few dances and the effects of the drinks, I started to loosen up. I could see Melissa nearby dancing with the other guy. A slow number came on and Melissa began slow dancing with her guy. Before I could react, my guy grabbed me and began slow dancing.
He pulled me close to him and held me tight, first rubbing his hand up and down my back, before slipping it down on my ass. I squirmed a bit but he held me tight and felt up my ass as we danced. The terrible thing was, I was starting to get a little turned on by it all. The slow number finished and he gave me a kiss before he turned loose of me.
When he let go of me, I scurried back to where we’d been sitting and Melissa ambled back as well, with the two guys following. As they got near, I decided I needed to pee and headed for the bathroom. I almost went in the men’s room, out of habit, but caught myself and realized that if I went in there like this, I’d really be in a world of trouble.
There were a few other women in the restroom, but they paid me no mind whatsoever. I found an empty stall, went in and latched the door. I pulled up my skirt and pulled down my panties and sat down on the toilet. I might have had a few drinks, but I knew damned well, I’d better not stand to pee.
I had a hard-on, which kind of surprised me. I didn’t think I’d get turned on my having some guy rub my ass and kiss me. I know that girls wipe after peeing, so I got some toilet paper after I peed, and just sat there trying to catch my breath and let my heart rate and my prick get back to normal.
I heard the women in there leave, then I heard the door open, and someone came in and went in the stall next to me and sat down. After a minute, I heard Melissa’s voice from the next stall.
“You okay, Casey?”
“Yeah, it just started getting a little too intense a little too fast.”
“I told the guys that you weren’t feeling well, and that you had a jealous boyfriend, so they’ve moved on.”
“We’ll wrap it up and go home. The two of us can have some fun there, then tomorrow we both have work.”
I pulled my panties back up and tucked myself back in. I smoothed my skirt down and flushed. I heard Melissa flush in the stall next to me. We both came out, looked and each other, and I couldn’t help but giggle. She gave me a sweet kiss, we washed our hands and left.
The guys were off hitting on some other girls. We found our tab had been paid, by the guys, I guess, so we went back home.
We raced to the bedroom and undressed each other so fast, we almost tore clothes. We dropped into bed giggling as we kissed and caressed each other. Melissa rolled me onto my back and climbed on top of me, teasing me for the longest time before lifting up and sliding my cock into her dripping pussy. She slowly sunk down on me until I was deep inside her, then began to slowly fuck me while kissing me.
I came inside her as she collapsed on me in her own orgasm. We lay there for a while catching our breath before resuming kissing. I played with her boobs with one hand as my other hand groped her ass. She squirmed around, keeping me still in her though I was steadily shrinking. I snuck a finger in her ass which made her wiggle around that much more.
I got hard again and as I did, she began to fuck me again. I finger fucked her ass as my prick enjoyed her cunt. She fucked me ever more frantically as I put a second finger in her ass, before we both came again. After we recovered, she got off me and had me roll over, getting on hands and knees. She put on her strap-on and lubed it up.
I felt the head of the cock ease into my ass and moaned. She stroked my ass and eased the dick further into me. I found that the more we did this, the more I got into it, and I was beginning to enjoy having her fuck my ass. She fucked me until I came , then we rolled over onto our sides with her strap-on still buried deep in my ass.
“I love you, Casey.”
“And I love you, Melissa.”
“Do you really love me?”
“Of course I do.”
“How much do you love me?”
“More than anything or anyone, ever.”
“What would you do to prove how much you love me?”
“Anything you want.”
“Absolutely. What do you want me to do? Just tell me.”
Melissa unhooked her strap-on, while leaving it buried in my ass. She climbed over me to face me, and kissed me. We kissed for a while, and I stroked her boobs as we did.
“You like playing with my boobs, don’t you?”
“I love it.”
“I’d love for you to have boobs that I could play with.”
“How do we - ?”
“Hormones. They’ll give you boobs, inhibit your facial and body hair, and make your skin softer, but you’ll still have that dick that I love.”
She reached out and stroked my cock, which began to get harder again as she touched it.
Melissa pouted and stopped touching my dick, and moved her face farther away from me on the bed.
“You said you loved me and would do anything for me, and the first thing I ask, you don’t want to do.”
“It’s just a shock. I’ll do it, but how do I hide boobs when I go to work?”
“It takes a while for them to grow, so no one would know until they started to get bigger.”
“And when they do?”
“Maybe when they do, you don’t hide it. Maybe instead of only dressing up for me evenings and weekends, you dress that way all the time, even at work.”
“Is that really what you want me to do?”
“You’ve been my girlfriend and my boyfriend. I still want you to be both, but with extra benefits.”
Melissa kissed me and touched me, and rolled me onto my back. As she did, it pushed the strap-on deeper into my ass, but I was happy, even more so as I got hard she she fucked me one last time for the night.
The next day, I started hormone treatments. I didn’t immediately change my appearance at work, though I no longer kept my hair back and let it fall more the way I did when I dressed up. Slowly, as my boobs began to grow, I began to wear the slightest bit of very subtle makeup to work. After several weeks, I went to human resources and told them I was transitioning and would be wearing female attire.
Company policies were pretty lenient, and they told me that was no problem and to report if I suffered any harassment. I dropped little hints to the people I worked with, many of whom had begun to catch on anyhow. Some of the others I had to be more forthright with.
My boobs grew to the point where I needed a bra for them, and as I began to wear my bra to work, I also switched to women’s slacks, tops, and shoes. I kept my makeup pretty subtle for work still but had my fingernails polished when at work, and in open shoes, it was obvious my toenails were polished as well.
A few people seemed bothered, but they grumbled to themselves and didn’t bother me. After a while, I switched to skirts instead of slacks for work most days. Some folks kind of avoided me, but many of the women welcomed me and were nice to me. I had occasional street harassment problems, but I guess no more than most women do.
As my boobs grew, Melissa loved stroking them and they became much more sensitive as they grew. One of her favorite things now was to have me lie back as she kissed and sucked on my titties. The shock was the first time she brought me to an orgasm just by sucking on my boobs. I felt the heat rising through my body as she kissed them, sucked on them, and played with them. All of a sudden, I felt pleasure rippling through my body, and was shocked because I didn’t ejaculate, even though I came.
One Friday, evening, Melissa told me we needed to open up our sex lives a little further.
“What do you mean? Open it up, how?
“Just go with me, Casey baby. Trust me, I think you’ll enjoy it.”
We went to one gay bar that we frequented, and were joined by Sheri, who I’d seen there before but didn’t know. Sheri was maybe a couple years older than we were but about the same size, with lovely shoulder length blonde hair, a pretty face, a nice ass, lips that begged to be kissed, and a magnificent set of c-cup breasts. From the hormones, I’d filled out to a nice b-cup, but Sheri had great boobs.
Sheri flirted with both Melissa and I, and at first I stressed out a bit, worrying how she would react to me having a cock. After a few drinks, I no longer cared much. Either it would bother her or it wouldn’t. If it did, she might run away screaming, but then Melissa and I would still have each other.
We went back to our place, Sheri with us, and began kissing and touching each other as soon as we got in the door. It took a while for the three of us to make it into the bedroom. I’d never been with a woman other than Melissa, so I wondered what Sheri would be like. I played with Sheri’s boobs through her clothes as we kissed.
Sheri had a pull-over top which she pulled off, under which she had a lacy blue bra, which accentuated her perfect tits. I unhooked her bra, and eased it off her and took my first look at her boobies. We all lay down on the bed and Melissa kissed Sheri as I kissed the perfect nipple on Sheri’s right breast. The nipple got very erect and Sheri moaned and squirmed as I licked every inch of that boob.
I sucked on her boob as though I was a baby, trying desperately to get nourishment from it. Sheri arched her back as she played with Melissa’s boobs while I enjoyed hers. I took my thumb across the nipple of that tit as I moved over to kiss the other one. This was the third set of boobs I’d ever had contact with, first Melissa’s, then my own, and now Sheri’s. They were firm and soft and wonderfully delicious.
By the time I’d finished with Sheri’s breasts, all three of us were down to only wearing panties. Sheri kissed Melissa’s boobs, and Melissa made it clear she wanted me to go down on her. She lifted her hips and I pulled her panties off, then planted a big kiss right in the middle of her pussy. I began licking it and sucking on her clit, while I began to finger her.
As I did, I was on all fours with my ass in the air, making love to her pussy with my mouth. I didn’t even realize that Sheri had stopped kissing Melissa’s tits until I felt my panties being pulled down. I kind of tensed up a bit, but she pulled then off me with no protests, then began to caress my ass. I enjoyed it and wiggled my ass around as she did.
I felt something going into my ass, and thought Sheri had gotten Melissa’s strap-on. I paused for a second to look around and realized that wasn’t the case. Sheri also had a dick and she was putting her dick up my ass. I gasped for a second, then Melissa grabbed my head and pulled me back onto her pussy.
I resumed licking Melissa’s twat as Sheri began to fuck my ass. I was a little uptight about it, but realized it didn’t feel much different from Melissa fucking my ass with her strap-on. If anything, this might have felt a little better. Sheri’s dick was warm and comfortable, as she began to slowly fuck me. She held my hips and stroked my ass as she plunged deep inside me.
Melissa pulled me tight and came on my face, as Sheri pulled tight and came in my ass. I could feel her dick throbbing and pulsing and felt her filling me up with her cum. As we all came down from this, Sheri spoke.
“Well, I’ve had you, baby, so it’s only fair to let you have me too.”
Sheri got on all fours and began kissing Melissa’s boobs again, with her ass out there available for me. At that point, I figured anything went, so I got behind her. She paused and looked back at me.
“There’s lube right beside you on the table.”
I lubed up my cock and eased up behind Sheri. I spread her ass cheeks to see her asshole puckering. She was twitching, and just waiting for me and my cock. I got the head of my cock right up to her ass, without going in. Sheri moaned and pushed her ass back, which got the head of my prick just inside her. I heard her sigh as I eased my way forward, gradually in and out of her, going deeper with each thrust.
As I got all the way in Sheri, her ass grabbed me. She was tight, perhaps surprisingly so. I began to slowly fuck Sheri, as she began to fuck me back.
“Harder, baby. Fuck me harder.”
It didn’t take long before I could feel an orgasm building up in me. I fucked her harder and faster until I plunged deep and held her tight while emptying my balls in her ass. I think I actually collapsed on her back and passed out from the intensity of the orgasm.
Melissa made Sheri and I wash our cocks off before we did much more, then we spent a long time kissing, touching, and fucking in all combinations until we fell asleep from exhaustion.
We woke up in bed together the next morning and spent a while kissing before the three of us got in the shower together. It was a bit small and rather awkward with three of us but we giggled, kissed, touched and fucked until we ran out of hot water.
Since then, Sheri occasionally joins us, and Melissa and I are happier than I ever dreamed that I could be.