We continued kissing, but some of that spark was gone now. At least her cock was still hard, so I knew that she still wanted to fuck. With girls, you have to work hard to read their emotions. With t-girls, you just have to feel to see if they’re hard or soft—and Danni was as hard as granite. I was stroking her, pulling back her foreskin and massaging her bulbous, smooth tip. She was even gently thrusting herself into my fist.
I reached down and wiped a bit of spit onto my cock, getting it nice and wet. Then I pressed my tip up to her tight hole. “Ready?” I asked.
“Sure,” she said, taking a deep breath. I started pushing in. She clenched at first, groaning and squirming slightly. I held her down firmly. I used the same hand that I had on her cock to push her back into me. I sunk deeper and deeper, pushing through her clenching. I could feel her anal walls throbbing just as hard as her cock. She was tight and possibly a virgin. I knew I wasn’t going to last long.
“Fuck, you feel so good,” I said.
“Please fuck me,” she said.
So I started to pump. She groaned louder and grabbed two handfuls of bed sheets, pulling them in towards her. I could feel every inch of her tight cavern—and I made sure to use every inch of my rugged cock, sliding all the way back until my tip was teasing her rim before plunging down again. I was pumping slowly at first, but it didn’t take long before I was slapping that ass repeatedly with my hard pelvis.
“Shit!” she screamed through clenched teeth. She clenched my cock again, which felt amazing. I had to bite down on my tongue so that I would end up coming in less than thirty seconds. I took my hand off of her cock so that I could feel her tits. She had implants, which were still a bit stiff, but they still felt nice. I squeezed them, making her nipples erect. She put one hand on top of mine and made me squeeze even harder.
“Fuck—you’re going to make me come,” I said.
“Pull out and come on me. I want your cum on my face,” she said.
“Okay,” I said between breaths. And I wasn’t far away—especially now that I had the image of myself coming on her face in my mind. I strained and clenched as the euphoria grew stronger and stronger. I tried to groan away the orgasm, but there was no stopping it. I pulled out and then I jumped up onto my knees as she rolled onto her back. I squeezed my cock tightly, holding my orgasm back for just one more second, and then I spewed my hot cream all over that beautiful face. A couple shots landed in her mouth, and then the rest coated her cheeks and chin. She licked up what she could reach and then she left the rest to gently dribble down her smiling face.
“That was awesome,” I said.
“We’re not done,” she said. She suddenly got into her feet, standing on that bed with her erection now just an inch from my face. “I’m close. Suck me off.”
“What?” I asked. My heart skipped a beat as my gaze lowered to that bobbing erection. I could see it throbbing. Her tip was a shade of dark red.
“I said suck me off. And then let me come on your face. C’mon—you’ll like it.”
I took a deep breath. My hands were trembling as I brought them up and wrapped my fingers around her girth. I gently pulled her foreskin back and then I leaned forward, allowing the cock into my mouth. And I felt a strange rush of excitement and relief. Sucking her cock wasn’t gross or weird like I was expecting. It felt strangely natural, and strangely satisfying. I sucked as much as I could fit in my mouth, and then I stroked what I couldn’t with a tightly clenched fist. I used the tip of my tongue to tickle the tip of her cock. It wasn’t long before I could taste the sweet tinge of her pre-cum. “I’m close,” she said. “Don’t stop.”
So I sucked harder and jerked faster. She started to squirm slightly. Her knees were trying to buckle but she was managing to stay on her feet. “Oh God,” she said. And then she tapped on my head, signalling me to spit out her cock. The moment that cock was out of my mouth, it started spraying. I closed my eyes and winced my face away slightly, but she reached down with both hands and held it in place while he cock did the spewing alone. Her cumshot was seemingly endless, coating my face with her white, hot load. I felt it dribbling down to my chin, over my lips. It had a sweet taste to it, which I discovered when I used the tip of my tongue to wipe off my lips. I actually didn’t mind the taste.
She sunk to her knees and kissed me, tasting her own brand, rubbing our brands together. She let a little giggle slip and then the room became suddenly quiet. I could see in her eyes that she was remembering my little comment from earlier: ‘This is just a fling—okay?’ I was remembering it too. I was sad now that our romp was over, and I was sad that our band was probably going to be finished shortly as well.
I ruined everything with sex. Or did I? Was it the sex that was ruining things, or was it my commitment?
I looked down at Danni’s perfect body and then back up at her stunning face, which was just as beautiful without makeup. Why couldn’t I be with her? Why did I care if people thought I was dating a tranny, but I didn’t care if people knew I was making music with a tranny? Why did I want to be single so badly—so that I could fuck girls on the road? Was it any more fun to fuck drunk chicks than it was fucking Danni? And with Danni, it was so much more than just sex. In just a couple of weeks, she was already my best friend. We had fun together. We already had memories together. There was still so much fun to be had—fun I would never get from one hundred slutty fans out on the road.
“Just a fling, right?” she said.
“Unless you don’t want it to be,” I said.
I watched as her eyes lit up, but she remained apprehensive. “What do you mean?” she asked.
“Well—maybe this could be a thing,” I said. “I mean, we make great music together. Maybe we could do other stuff together too.”
Mimi didn’t leave the band because I fucked her. She left because I couldn’t commit—I was scared to commit. But with Danni, there was no fear—just excitement. I wanted to commit to her. I wanted everyone to know that we were together. And I was terrified that she just wanted our little romp to just be a fling.
“You’re saying you want to be, like, my boyfriend?” she said.
“If that’s cool,” I said. My heart was pounding.
A big smile suddenly crossed her face. “Sounds good to me,” she said. And then we kissed again. I got to taste my own cum, which wasn’t nearly as tasty as he cum. I threw her down on the bed and we made out for the next ten minutes, until our cocks were rock hard once again. Then, it was penetration time all over again. This time, she went first, bending me over while reaching around to jerk my cock. I’d never been penetrated before. It didn’t hurt like I thought it would. It was actually kind of nice—even when she came inside of me. The feeling of her cum oozing out of me was a strange feeling, but I knew that I would get used to it—I already kind of liked it.
We didn’t end up going straight home the next day. We stopped in Jasper, checking into a nice hotel with some of the money we made on the road. We didn’t have a show in Jasper—we just stopped for the memory. We went for a nice hike the next morning, and then we fucked a few yards off the path. It was a strange walk back to the car, with her cum oozing out from my asshole and filling up my undies, but again, I kind of liked it.
We talked the whole five-hour drive home that night. She stayed the night at my place and then we spent the morning jamming. I was getting a taste of what life was going to be like with Danni—and I loved it.
THE END
THE SISSY DEAL
Vinnie has cut off contact with everyone from his high school, except for Theo, Jimmy, and Ben, his three friends who suffered the same torment from the same cruel bullies. When they get together every year for a weekend at Theo’s cabin in the woods, they don’t talk about those traumatic days, where the jocks and the cheerleaders would pull the boys into empty classrooms and dress them up like girls for a few laughs.
But one night, Theo decides to finally face those nasty memories. He’s started seeing a therapist, a
nd his therapist’s advice is to start being more open about his past. And who better to be open to than the guys who suffered the same treatment?
During their vulnerable conversation, it comes to light that the men all still have their V-cards. The high school bullies left them all with intimacy issues that have stopped them from reaching that final base. And now, Theo has an idea to help them all get past their issues, and it involves dressing up like a girl, facing those old memories, and taking one for the boys.
CHAPTER I
I did my best not to think about high school, but even many years later, those memories still came into my head from time to time, unwelcomed. And of course it was never the good memories, not that there were many.
I’d made a point of deleting all of my old classmates off of my Facebook. It was nothing personal for the most part—I just didn’t want to think about those terrible hallways and those nervous classrooms. I avoided cafeterias whenever I could. I even turned down a good job at a good hospital because they had the cafeteria on the same floor as my ward. So I ended up taking a job across town—an extra forty minutes of driving each day, just to avoid those embarrassing high school memories.
I only kept in touch with three guys—guys who were my friends because they suffered the same pain as me through high school. They were the only reason I got through those last two years.
There was Ben. I met him during lunchtime one day, when I quietly slipped into the school’s boiler room to eat my lunch. It was the only room in the whole school where I could be safe from the torment of the bullies and the judgement of the girls. I walked around the boiler, headed for my usual corner, and then I saw him sitting there, in the little folding chair that I usually sat in. I stared at him for a minute, trying to decide if I should run or if I should chew him out and tell him to scram. And then he said, “I’m sorry, am I in your spot?” I thought he was one of the kids from the junior high—our school was attached to a junior high school, though the hallways were separated for the most part. But I would quickly learn that he was in my grade—just much shorter and thinner than the other guys—even shorter and thinner than me.
“Kind of,” I said. “And can you do me a favour and don’t tell anyone about this place. I’m kind of running out of places to go at lunch.”
He stood up slowly and began sulking towards the door, and I could see a familiar pain on his face. I knew what he was going through, even though I didn’t. So I stopped him and told him he could eat in that boiler room with me. And that’s when noticed he had little smudges of what looked like makeup around his eyes. “Are you… wearing makeup?” I asked.
He closed his eyes and looked down at the floor. He told me his story. A few guys from the football team and a few girls from the cheerleading squad had grabbed him after first period and pulled him into the girl’s bathroom. They pulled off his clothes and then made him dress up like a girl. They even forced him to sit down, so they could do his makeup. And judging by the streaks of mascara down his cheeks, it wasn’t something he wanted.
And I suddenly didn’t feel quite so bad about my own predicament—little did I know that the exact same thing would happen to me just a week later. But until then, it had only been emotional harassment. They called me girly boy, even after I cut off my long hair. One guy even liked to call me “Pretty Hips,” apparently because I had wide hips like a girl—and I did have a hard time finding pants that fit in a flattering way.
So Ben and I ate lunch together every day after that.
And then there was Jimmy. Ben and I were late leaving school one day when we saw one of the cheerleaders pounding on the locked emergency exit behind the gymnasium. She was in the whole cheerleader getup, even with the gold and blue pom-poms around her wrists. “Let me in!” she yelled. She kept reaching down to tug down her tiny skirt, though I don’t think any amount of tugging would help her with the cold. We could hear in her voice that she was crying.
Even though she was a cheerleader and the cheerleaders were notoriously cruel to Ben and I, we went over to see if she was okay. “The door over here is open,” Ben called out as we got closer. “You can just go around.”
She looked at us with tears running down her face. “What are you looking at?” she asked.
“Are you okay?” Ben asked.
“I’m fine. Quit looking at me!”
And that’s when we both realized we weren’t looking at a cheerleader. We were looking at a boy named Jimmy, who the cheerleaders had dolled up and then pushed outside before locking the door. Jimmy was another victim of the high school torment—another small guy who could unfortunately fit into girls’ clothing. But Jimmy’s case was especially unfortunate because he had a higher voice than most of the guys, and his body was naturally hairless. As we stood there staring at him out behind the gymnasium, he pulled the blonde wig off of his head and threw it on the ground. We found him the next day and invited him to eat lunch with us in the boiler room. He told us many stories of bully cruelty.
Finally, there was Theo. We didn’t see Theo getting bullied. We just heard the rumours going around one day. When whispered rumours reach losers like me, you know that they’re big deal rumours. “Did you hear what that Theo kid does on the weekends?” one of the guys in my math class asked me. I looked over at Theo, who seemed like a normal enough kid. “He dresses up like a girl and then he lets men have sex with him. He even charges them.”
Theo became the laughing stock of the school once that rumour had reached every pair of ears. It was nice for a while, having the attention on someone else. But it wasn’t long before I started feeling bad for the guy, so I approached him during lunch one day and invited him to the boiler room. And then that’s where he ate lunch every day until graduation—that’s where all four of us ate lunch every day until graduation, where we were safe from the torment of the boys who were blessed with boyish bodies and the girls who loved making our lives hell.
And the torment went on until that final graduation day. I made the mistake of going to prom alone. I wasn’t even there for an hour before they grabbed me when I went to the bathroom. “No date?” one of the jocks asked me with a big grin on his face. “No worries. Carl doesn’t have a date either. You can be his date.” They dragged me away and then tied me to a chair. The girls were already there with their makeup. They got me naked, even pulling off my boxers. They pulled a pair of red panties onto me before wrestling a little red dress onto my body. I didn’t fight. After years of torture, I knew not to fight. I even closed my eyes and remained still while they did my makeup. I knew it would be over sooner if I just let them have their fun.
I tried not to cry. I thought that they would just have more fun if I cried. I did my best to give them nothing, hoping they would get bored sooner. But they still ended up dragging me back to that gymnasium where everyone was dancing. They pushed me onto the dance floor and said, “Hey Carl. Your date’s here!” Then they all started laughing. Carl grabbed me and started dancing with me, pulling me from side to side as the tiny skirt of my dress danced up and down, probably showing off my butt and maybe even the bulge of my cock in my panties.
He came up behind me and started grinding against me. I could feel the hard bulge of his erect cock through his pants. I could feel his hot breath tickling my neck. I managed to slip out from his hold. I ran off to that boiler room so that I could hide until the dance was over.
I wasn’t the only victim that night. Ben ended up getting the same treatment as me, and then he ended up running off to that boiler room. Then Jimmy showed up in a tiny green dress. Then Theo stumbled in wearing a pair of high heels. “At least it’s over after today,” Theo said. And even though I was wearing a red dress and makeup after having been humiliated in front of the whole school, that little comment still brought a smile to my face. It really was over. I would never have to see any of those jocks again.
And I didn’t see those cruel jocks or those mean cheerleaders ever again, unless you count the time
s they showed up in my nightmares. We never even talked about them again when we all met up, and we would meet up twice a year: once around Christmas, when we were all back for the holidays, and then once during the summer, when we would all go to Theo’s cabin for a weekend in the woods.
Ben’s growth spurt never came. He remained 5’2”, weighing just over one hundred pounds. Jimmy’s voice didn’t deepen much. He always had that voice that was easily mistaken for a girl’s. Sometimes when he called, that voice caught me off guard. I never stopped feeling bad for him, even though my growth spurt never came either. I was stuck at 5’5” and 120 pounds. Theo was the only one who grew to be taller, almost reaching six feet tall—which was enormous compared to the rest of us.
They were the only guys I still talked to from those horrible schooling days, but we never talked about the torment. I never told anyone about those times the cruel kids pulled my clothes off before dressing me up like a girl. I didn’t even tell my therapist—the thought of telling those stories out loud made my skin crawl. I would still have nightmares about being forced into women’s clothing. I had one recurring nightmare that was especially bad. The jocks would get me dolled up and then they would all look at me and start laughing. I would look down and see that I had an erection. Then, they would make me jerk myself off in front of them. And in my nightmare, it was terrifyingly easy to get off. The feeling of the tight lace against my skin made my heart throb and the mere thought of satin would make drool form on the corners of my lips.
But that was just a nightmare. I didn’t actually feel that way about getting dressed up like a girl. Thankfully, I never actually got an erection in front of anyone, and I was never forced to jerk myself off—though all of those mean kids did see me naked against my will on numerous occasions. But it didn’t matter—those days were all behind me. I knew that I would eventually forget about those times. I hardly remembered elementary school after all—so it made sense that I would one day hardly remember high school, right?
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