Casey Blossoms

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."

"But, what..."

"Casey, dear, do you like girls?"

"Yes."

"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.

"Should I..."

"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?"

"Sure."

"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.