The Perils of Young Guys

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up.

I met Jack and Kyle in my late teens after a night out at a party. Jack and another friend of his were my first experience with sex as a dressed girl. The whole experience is described in my first published story. That night I gave my first blowjob and had my first anal sex with a guy. For six months afterward I continued to hang out and hook up with Jack and Kyle; but it was very different. Jack was bi-sexual; but Kyle was gay and wasn't into my female persona. Jack seemed to accept it sometimes. Most of my experiences with Jack and Kyle were not dressed as a woman, or in my femme persona at all, so I don't really talk or write about them much. As far as Kyle, most of the time our encounters involved receiving a blowjob from him late at night whenever I slept over at their apartment. Jack was a bit of an alpha top and more enjoyed cornering me in the kitchen, in a men's room, or a private room somewhere, and fucking me against the wall. Each time I was in male clothes and this just wasn't how I enjoyed sex - unless I was with a real woman (or CD or TS!)

My last encounter with Jack and Kyle was in the bathroom of a gay club we visited a few times. Jack had pulled me into a bathroom stall and had me pushed against the wall with my jeans at my knees, pounding my ass. After he finished, Kyle stepped in behind me and began fucking me from behind. Once Kyle was finished and pulled out, I leaned down to pull up my jeans and noticed two older gentlemen standing outside of the stall facing me while they jerked off. One of them was my old high school history teacher. They had been watching us the entire time and were just finishing up themselves. I moved away to a new town shortly afterwards and never looked back.

It was in my new town and new life that I was more free to be girly and this is where I met Missy and Caleb (and Jones!). Missy and I dressed together and she had an 18 year old brother at the time, who apparently lusted after me. I'm not sure he was lusting after a crossdressing guy so much as he had never seen me not dressed and was lusting after what he recognized as an easy, available girl. Jones by the way was an older man I dated for a short while, I talk about him in another story.

Fast forward four years and I'm now 30 years old and fierce if I don't say so myself. I've been living alone as a girl now for the past three years and I don't have much contact with Missy anymore. Missy was on a journey to be a real girl and started hormone therapy a year before. She didn't associate with crossdressers like me anymore. I couldn't blame her, she was ultimately committed and I was just pretending; but it still hurt sometimes.

It was Halloween and like all crossdressers I chose to use the holiday to dress in the open. It's the perfect cover! I chose a schoolgirl outfit with a short pleated skirt and dress shirt. I didn't have much else, so with full makeup and my favorite wig, this would need to work. I looked amazing if I do say myself! I had recently invested in some nice, expensive false tits and had them stuck to my chest with medical adhesive. Because these tits were attached, I didn't need a bra so the nipples poked out a bit and you could see them slightly through my shirt.

I had been answering the door all night as a very mature looking school girl and handing out candy to the little darlings. Sometimes I got pickup lines and chit-chat from the dads and that was fun; but for the most part it was pretty tame. I got a knock at the door and opened it to find three college aged guys dressed as Spartans. The bare pectorals and chiseled abs alone were worth the price of handing out candy all night :)

I got a couple of whistles and comments from the boys, which were nice; but once I passed out the candy and the other Spartans peeled away, one Spartan remained. I vaguely recognized him as Missy's brother Caleb. He had definitely grown into himself over the years and was now a handsome, filled out young man. All I could says was, "Hi Caleb" and he responded with "Hi Miss Amanda", which I thought was extremely sweet, and the fact that he used my femme name so endearingly gave me a few small butterflies in my tummy. We exchanged looks - he wanted to fuck me and I wanted to be fucked by him - but instead I closed the door and we both moved on with our lives.

About an hour or so later, as the trick or treat crowd started to wind down, I heard a knock at the door. I answered and found Caleb standing there. We didn't say a word to each other, I just stepped aside and he walked into my apartment. We stood there very awkwardly not even speaking to each other. We just sort of stared at each other uncomfortably.

I don't know how the candy got on the floor. Maybe Caleb dropped it or maybe I dropped it subconsciously; but I kneeled down to pick it up either way. While I was kneeling to pick up the candy, Caleb pulled his cock out and it was already fully hard. I felt his hands on the back of my head and he was pulling me closer onto his cock.

I am no blowjob queen to this day by any means, mostly due to a lack of practice, and this is how that came to be. Caleb pushed my head onto his cock as I opened my mouth. I could feel his hands on the back of my head as his cock pushed into my mouth, over my tongue, and touching the back of my throat. He held the sides of my head as he pulled back and then thrust deeper into my mouth. He pushed his hips back and forth and slid his cock in and out of my mouth a few times and on one stroke he pushed his cock deep into my throat with my face smushed against his pelvis. Then it happened. I gagged and threw up in my mouth. Caleb either didn't notice or didn't care and he just kept going. I breathed the vomit and saliva through my nose and it burned like nothing I have ever felt before. I pulled back and stood up. I was NOT doing this any more.

Caleb took two steps closer to me as I took two steps back. I only stopped when my back hit the dining room wall. Caleb leaned in and began kissing my neck, his left hand squeezed my fake tit as he rolled the nipple between his fingers. It was awkward because I couldn't feel a thing; but Caleb was clearly into my fake tit. I reached down and wrapped my hand around Caleb's rock hard cock and started to rub it up and down. He really got focused on my fake tit and at one point lightly bit the nipple through my shirt. When I saw this, I let out a half sigh-half moan to play along. I asked if he had a condom and he replied no, so I stepped around him to lean against the dining room table so I could reach for a stash of condoms I knew where in the top drawer of a dish cabinet I had there. I pulled a condom from the drawer and a bottle of lube I saw there as well (lucky). I unwrapped the condom and rolled it over Caleb's cock. I squirted some lube in my palm and rubbed it over Caleb's cock really well, then reached back into the back of my panties and wiped what was left across my asshole. I leaned in to give him a deep kiss, and while we kissed, Caleb put his left hand on my shoulder and his right hand under my knee and we leaned back onto the dining room table.

Caleb grabbed my hips and quickly slid my whole body to the edge of the table, then grabbed the crotch of my white panties in his fist and pulled. The panties tore; but only slightly, so Caleb grabbed at my hip and pulled the fabric tight until that side of the panties ripped. My cock and balls were now on full display and Caleb's eyes widened and he took a step back. Apparently, a girl with a dick and balls was not in Caleb's wheelhouse, so I quickly sat up and pulled my skirt over my goodies, then leaned back on the table, raising my knees and opening my legs. Caleb leaned in and slid his cock into my ass. He immediately began a rapid thrusting and pumping. I rubbed my hands along his firm shoulders and down his muscular back. I worked my hands around to his abs and could feel each one flexing every time he push his cock into my ass. I ran my fingers up and across his chest and through his thick black hair.

Calebs thrusts grew more frantic and he began to push deeper until suddenly he stopped and pulled his cock out. He gripped by waist again and slid me forward and off the table onto my feet. He pulled my shoulder around, put his hand in the center of my back, and pushed me face down onto the table, then lifted my skirt and pushed his cock into me from behind. His strokes were rapid and frantic again as he pounded me from behind. A little too frantic as at one point my balls became positioned between Calebs thigh and the edge of the table and on the next deep thrust, they were pinched between the two. I thought I would throw up from the pain and I pushed back on Caleb's leg to stop him; but no such luck. I took deep breaths through the pain and nausea while Caleb kept pounding away at my ass. I was honestly over it all by this point and just waiting him to come.

I could feel Caleb's hands on my butt cheeks, almost spreading them apart as he drove his cock in and out of ass and then what felt like his thumbs in my ass on either side of his cock - almost stretching my asshole while he fucked me. Caleb began to breath deep and his strokes slowed and pushed deeper, pressing hard against my ass. Caleb climbed onto the table almost laying on top of me. He put his arm around me, across my chest, and pulled my close. He was breathing heavily in my ear and pushing deep into my ass - he was coming.

After a few minutes of lying motionless with his cock in my ass, Caleb slid off of me and started straight toward the front door. He grabbed the pieces of his costume that had been thrown to the floor and stopped briefly to look back at me still lying on the table. "Bye Miss Amanda", he said with a sly smile like a little boy who just made off with the last cookie. He closed the door and I never heard from Caleb again.

Later that evening as I was cleaning the apartment I realized I could not find the used condom from earlier with Caleb. I laughed a little as I pictured Caleb heading for the door and driving home with the condom still on his cock. It wasn't until a day later (when I finally pooped again!) that I found the condom floating in the toilet. Apparently the condom had slipped off at some point and been pushed deep into my ass. Then it hit me, that's what was going on with Calebs thumbs stretching my asshole. Caleb was actually sliding the condom off while he was fucking me, so he could finish inside me without the condom!

Caleb was a sweet young man and his body was certainly a joy to behold; but these lessons along with my prior experiences with young men (Jack and Kyle) have made me a bit jaded. These days I will pass on even a buff young guy over a smooth older gentleman. All in one night I had been throat fucked until I threw up, smacked in the balls, and tricked into barebacking. I was done with men for awhile... at least until I met Ty; but that is another story for another time! XO