Shemale Stories

[GroobyKrissy]

Unfortunately, I was young and easily excitable at the time. It wasn't very much longer that I could feel the waves building to a peak and then come crashing down all around me. It was incredible...so much better than when it was just me and a magazine. I was breathing heavily when I felt a warm wetness on my stomach. Surprised, I looked down and saw Rick's head over my stomach... he was licking the cum off my body with short strokes of his tongue. He glanced up at me and smiled...I smiled back and let my head fall back to the bed. Rick continued until he was satisfied there was not one spot of cum left on me and then began kissing and licking my thighs and my now deflated cock. I continued to lay there, not quite knowing what to do.

After a few minutes, I felt a warm sensation that took my breath away. Rick had slipped my limp cock all the way into his mouth and was slowly sucking on it. I could actually feel myself getting harder and harder again by the second. Soon, his efforts were rewarded with a second load which he took completely in his mouth. Strangely, I remembef feeling so honored that he would go through all this effort just to make me feel this good.

As we both lay there panting, the thought of what had just occurred hit me like a ton of bricks, followed by a flood of tears. "Hey hey hey," Rick whispered, running his hands up my body to my face. "Don't cry... didn't you have a good time?" I think I managed to sniffle out a pathetic sounding, 'yes'. "Well, what's the problem then?" Silence...I just couldn't bring myself to say what I was feeling. "Well, if you want, we can keep this a secret... would that be ok?" I nodded. "Ok then, it's settled, I won't tell a soul." Somehow, that made me feel a whole bunch better. I felt Rick's hands caressing the side of my face, wiping away the stray tears that had fallen there and then, he leaned close and kissed my forehead. "Would you like to meet again?" he asked. An affirmative nod from me started a summer of meetings that found me exploring my blossoming sexuality...

It was easy to meet with Rick since the club was only a few miles away. I soon took to riding my bike to the club and Rick where we would invariably end up in the 'Guest Room' exploring each other's bodies. It was probably ten or so meetings down the wire when I called the club asking if Rick was there. When he got on the phone, I asked him if he'd like for me to come over in the afternoon. He said that he had a better idea, asking me if I knew where the ********** hotel was in Monterey. I told him I did and he gave me a room number and time to meet him there. I have to admit, I was VERY intrigued.

I showed up at the room at the specified time and knocked lightly. Rick opened the door and ushered me inside. It was a VERY nice room and on the bed I noticed several packages. "These are for you," Rick said, coming up behind me. "But, you have to open them in order." He handed me the first package. It was simply wrapped and very light. I opened it carefully, not quite knowing what to expect. It was definitely nothing I ever expected. Inside was a black garter belt with a very familiar logo on it, 'Victoria's Secret.' Also, was a black, lacy bra and matching panties, and a package of black, seamed stockings. My confusion was probably pretty obvious as Rick's voice quickly broke the silence, "I just think you would look adorable in these. You can try it once and then if you don't like it, you don't ever have to wear them again. But, would you do this for me, just this once?" I gave a nervous laugh and asked, "But, aren't these for girls?" He laughed, "Well, girls wear pants don't they?" Silly logic I know, but in my confused state of mind, it seemed to be enough of an answer. "Well, ok then."

He handed me a second package off the bed which I opened with even more curiosity. Inside this one was a very sexy black corset (which i still have to this day!). At the time, never having seen a corset before, much less worn one, I was actually wondering what it was and had to ask Rick to explain it to me. After he had finished explaining all the ins and outs of corsetry, he handed me the last package. This one felt a bit heavier and I knew what it was even before I opened it. "I guessed at your size so I hope they fit." Rick said. I think this last gift was what really hooked me into the whole crossdressing thing... a beautiful pair of black patent pumps. I slipped one on to see if it fit or not and it seemed to magically slide on... it looked so natural on my foot...definitely love at first sight. "Well, what do you think?" Rick asked. I think subconsciously I already knew I was hooked, but I gave a very political answer... "Well, I suppose it can't hurt to try it once." I headed to the bathroom with the gifts to try to figure out how everything went on.

In the bathroom, my heart pounding, I opened up the package of stockings. They felt so smooth against my hands that I couldn't wait to get them on my legs. I pulled them up, and in hindsight, it's a miracle I didn't put runs in them in my naivety! It took me some time to get the seams straight but eventually, I got them running vertically along the back of my leg. In the mirror I definitely liked the way the line accentuated every lean muscle of my lean calves and thighs. I ran my fingernails from my knee to the top of my thigh along the stocking and could feel myself getting harder and harder. I had to stop or else I was going to cum right then and there!

[GroobyKrissy]

I pulled on the lacy panties and again looked into the mirror. My butt looked so cute framed in the lace that I couldn't help but be jealous of the women who got to wear such things every single day! The bra was easy after figuring out the fastener... I'm not sure if Rick was thinking of me or himself when he bought the bra, but it had a fastener in the front which made things very easy for my first time dressing. The corset was a whole different matter... I tried to figure out all the strings and hooks but was just getting frustrated so I called out to Rick, "Ummm....I don't think I can put the corset on alone?" "That's ok," he called back, "Just put everything else on and I'll help you with that." I slipped on the black pumps and took my first step in heels. Turns out, I was a natural. I half expected to fall on my ass after the first few steps but found walking in heels not a difficult challenge at all. So, after one last glance in the mirror, I grabbed the corset and headed for the door. "Here I come!"

As soon as Rick saw me I knew his cock was rock hard underneath his pants. His eyes said it all. I can't say that I can totally relate, but, I at least have a pretty good idea what a woman feels like when men are 'undressing' them with their eyes. I found the sensation to be extremely flattering. I threw the corset at him and teased, "Stop staring!" "Baby, you look so hot," he replied, "I can't help it!" I looked down, feeling my cheeks crimson at his words. He got up off the bed and walked over to me. "Turn around," he said. I complied and soon felt his hardness pushing against the small of my back. I moaned, reaching back with my hand and rubbing the front of his pants. "Oh baby," he said, "I can't wait to make love to you today." Now, thus far, 'making love' had only consisted of lots of foreplay, rubbing, kissing, and sucking. This time, I knew exactly what he wanted... he wanted to make me his girl.

The change that came over him was incredible. Before, he was always very gentle and slow... this time, he was much more intense. He pushed me towards the bed and in the high heels, I tumbled easily on it. He slid over me and I could feel the weight of his body pressed against mine. It is an incredibly sexy feeling having the weight of a man pressing you down into the mattress and feeling a rock hard cock poke against your skin. We kissed for a while, slowly and then building up until he was fiercely ramming his tongue into my mouth. I have to admit, I was just a little bit scared with this change in his behavior...but, it also really really was starting to excite me. His hands were roaming up and down my body, the corset now just a piece of clothing discarded on the floor. Every time they passed my over the bra, I could feel the fabric rub against my nipples making them more and more sensitive and hard.

My knees were now bent and my legs wrapped around his back as he moved on top of me, kissing everywhere. His mouth found its way to my little nipples and he sucked eagerly at them, first one and then the other. The explosion of feeling from his sucking was enough to start the pre-cum oozing from my hard cock. His hands moved over the panties and rested on the ever increasing wet spot now developing there. "Mmmmmm..." he moaned, "Is my little girl getting all wet for me?" The next words were so natural they just leaped from my lips, "Yes, Daddy! You're making your little girl so hot!" He whispered in my ear, grazing the lobe with his teeth, "Do you want to be Daddy's little girl?" "Yes, Daddy," I moaned, "Please make me your little girl." "Are you going to be a good little girl?" At this point, he could have asked me anything and the answer would have been, 'yes'. But, without even giving me time to answer, he moved onto the next question... "Are you going to be a good little slut for Daddy?" Now, this was a new word. I mean, I knew what a slut was...but he had never used it in reference to me and somehow being called one just about threw me over the edge. My panty covered cock now started thrusting upwards against his palm. "Mmmmm.....good little slut!" he whispered. "I'm going to make you Daddy's little fuck slut today." "Yes Daddy," I begged, "Make me your little fuck slut!"

I felt his hand slip lower and a finger playing with my virgin hole. Out of nowhere he produced some lube and proceeded to squirt a generous amount right down the crack of my ass. The coldness of the liquid surprised me and I let out a breath that I'm sure he took for pleasure. I suddenly felt my hole being penetrated by what felt like a massive rocket trying to shoot it's way into me. I squirmed underneath him and he said calmly, "Just relax and it will feel good soon...it's going to hurt a little first though...it always hurts for little girls the first time." DAMN RIGHT! I thought the finger was bad...but, it was nothing at all compared to what was coming next.

After a few minutes of having his finger assault my tender ass, he finally decided it was time to 'take my cherry.' He moved my legs from around his back to the top of his shoulders and I couldn't help but feel very vulnerable with my ass exposed and my legs in the air. I also couldn't help but notice how sexy my legs looked encased in nylon and topped off with those black heels that just screamed, 'FUCK ME!' Which was exactly what happened. Rick's cock was hard... HARD. And, I felt every millimeter as he pushed it slowly inside me. It hurt so badly I thought about screaming but was able to hold it back. Instead, I concentrated on watching Rick's face as he took my virginity. The look on his face was incredible... he was totally wrapped up in this little fantasy... fucking a cute, little Asian girl for the first... he looked down at me and I swear it almost made me cum. It wasn't very long before I felt the 'pop' as the head of his cock broke past my opening and slid down inside me. then, little by little, he pushed further until the entire length of his cock was buried deep in my ass. Then he began pulling out...

After all these years, this still remains one of my favorite things. I love having a cock buried deep inside me to the balls and then feeling it slowly being pulled out. It's so hot because it makes you want to be filled back up again...then, when he pushes back inside you...man! pleasure city. But, that was just a side note. Anyway... he turned out to be right after all. For all the pain in the beginning, it wasn't long until I began to realize that every time he entered me, something inside me punched the pleasure button in my brain. Soon I was thrusting back against his cock as much as I possibly could to try to maximize that feeling with every thrust. From our past experiences, I could tell that he was getting close to cumming and this brought up a whole new set of questions for me to ponder. Please remember, I was young AND STUPID! I didn't really even think about condoms or anything even remotely resembling safe sex at that point in my life. I was just wondering where he was going to cum. Well, that question was soon answered. I could feel his whole body tense up in a pre-climax quiver. And, then, with a couple of hard thrusts, I knew he was filling the inside my ass with his cum.

I'm not sure if it was the pure submissive feeling of having my ass pumped full of cum or just the fact that I was so turned on by that time; but, with just a couple jerks on my own hard, panty covered cock, I quickly emptied my own load. The spasm my ass made around his cock must have felt pretty good because with each wave of pleasure rolling over me and echoing in my ass, he moaned in my ear. "Mmmm... you're such a good little girl," Rick breathed. We lay there until I felt his hard cock getting soft and finally falling out with quick pop. It felt strange...being empty. He kissed me lightly on the cheek and rolled besides me, wrapping his arms around me. I lay there until suddenly I could feel his cum oozing from my tender hole.

Embarrassed, I unwrapped myself from his arms and made my way to the bathroom door. I could feel the cum dripping down the inside of my leg and onto my new stockings. I suppose there was no turning back now...I was completely hooked. And, ever the girl, I remember my last thought as I entered the bathroom being, "Damn, now I have to wash these!" A girl's work is never done.

The End

[randolph]

Hey Crissy, a great story, very sexy and well written.

[randolph]

It is easy to post comments and pictures, it takes time and effort to write and post stories, however. Some of us like to write erotic stories but its not worth the effort if there is little or no feedback. Just wondering if many of you would like to have more stories posted.

[ila]

I have a story that I finished about 3 months ago. It's very long though and would take between 10 - 15 posts to put the whole thing on here. I've been reluctant to do so because the story is so long. I will do so if there is a demand for it.

[randolph]

Originally Posted by ila

I have a story that I finished about 3 months ago. It's very long though and would take between 10 - 15 posts to put the whole thing on here. I've been reluctant to do so because the story is so long. I will do so if there is a demand for it.

You have my vote.

[ila]

Part 1

Gina stepped from the shower and grabbed a towel. She quickly dried herself off and then turned towards the oversized bathroom mirror. She turned left and right examining herself with a critical eye. Gina was satisfied with what she saw. At a petite 5’ 4” and a featherweight 116 pounds her body was perfectly proportioned. Gina was pleased to notice that her 34B breasts were still firm with not even a hint of droop. She examined her sensitive nipples which Michael, her husband, loved to fondle, caress, and suckle.

Gina now faced the mirror and ran her hands across her smooth firm tummy. She could feel her underlying toned muscles that helped to shape and define her tiny waist that flared out to her elegant hips. Gina let her hands slide across her smooth, hairless, tight pussy; a pussy that Michael loved to tongue to ecstasy. She shivered in anticipation of feeling Michael’s eight inch long, thick, hard cock sliding in and out of her. That would be much later right now she had to finish getting dressed.

Before picking up her hairbrush, Gina gave her cute tushy a quick once over. It is still smooth, firm, and round with not even a hint of jiggle. It’s no wonder Michael adored her and her body. Gina started brushing her shoulder length, wavy, medium brown, silky hair that was shimmering in the light.

With her hair done Gina padded out of the bathroom and took a seat in front of her makeup mirror. She leaned in close and brushed an imaginary speck off her flawless skin. Next she applied her eye makeup to highlight and emphasize her sparkling brown eyes. A few more minor touches and finishing with her understated lipstick and Gina’s exceptionally pretty face was even more gorgeous. Michael often told her that women secretly envied her and men covertly lusted after her.

Meanwhile Michael was off getting ready for this evening. This was to be one Michael’s and Gina’s special nights out. Gina and Michael take turns being the one in charge for these special nights. These nights have often produced unexpected and kinky results which both of them have enjoyed immensely. Tonight Gina was in charge. On a whim she had made Michael give himself a thorough enema. Gina had gotten turned on watching Michael and had gone off to her bathroom to give herself the same treatment; a decision which would prove to be propitious.

Michael stepped out of the shower. He is six feet tall and 195 pounds with an athletic build. Michael hits the gym quite often and all that workout time had done wonders for his physique. His normally well-muscled body had bulked out leaving his broad well muscled chest with highly defined pecs. He gives new meaning to the phrase ripped. Gina had recently taken Michael to a spa for an upper body and pubic waxing. He had not a hint of hair from his balls to his neck. Michael liked the new look. His rippling muscles stood out like a Greek sculpture.

Michael rubbed down his chest and stomach followed by his legs, feet, and then working back up to his to tight football player’s ass. Finally Michael dried off his arms. He noticed that all that work on free weights had made his biceps bulge.