It was the spring of 1999, and I was 18 years old.
Dave was off to college in another city. When he was home we'd get together and fuck. Sometimes, he'd spend the night, but most times he’d go to his parents' afterwards. I wanted to go see him, but he always had reasons (really, just poor excuses) for me not to come. He asked me up 2 or 3 times, when his roommate was gone.
The last visit, he introduced me to his roommate, Fred. Fred was tall, good looking, with a nice smile and dark eyes. He played on the football team. Dave mentioned to me that Fred was interested in me, and that I should be nice to him.
Fred was out and I was hoping to fool around with Dave, but Dave said he had a late class and a tutorial he needed to attend. He left me alone and promised he’d be back in a couple of hours.
Fred returned shortly after Dave left. We visited a few minutes and I found I enjoyed Fred’s company. I felt relaxed.
“May I kiss you? He asked, suddenly.
Dave told me to be nice (meaning it would be okay to fuck him), so I raised my lips to meet his. Fred drew me into his arms and kissed me lightly. I wrapped my arms around his neck and returned the kiss with more passion.
After a couple of moments, he pulled back and said, “Wow!” Then he asked, “Is it true about you?”
I wasn’t sure what Dave had told him so I waited for him to continue.
“I heard you like sucking cock and taking one anally.” When I nodded yes, he asked, “May I fuck you? I have a girlfriend, but she doesn’t suck me often, and won’t take me in her ass.” Then, “I won’t be upset if you don’t want to.”
I smiled and he undressed and sat on the sofa. I straddled his lap and removed my top. (I’d started hormone therapy and my breasts were small, but rounded.) He kissed and licked my nipples while I lubed his cock. I moved my panties aside and slid his stiff cock into my waiting asshole.
I rode him for several minutes. He had a nice seven inch cock, not too thick, not too thin. Just right! It felt wonderful inside me! He kissed my mouth then moved to my breasts, then back to my mouth. I felt good all over.
He stiffened, then pulled my hips down as he filled my ass with his hot load. I rode him a few more minutes, then knelt to take his now limp cock into my mouth. I soon had him hard again. I bobbed up and down slowly, savoring my flavor on him. I’d take him all and run my tongue across his balls. He groaned again and pulled my head all the way down, filling my mouth with his salty load.
I excused myself to clean up. I returned after my shower to find Fred gone. I was disappointed and lonely. Then Fred emerged from his room, nicely dressed.
“Would you like to get a bite?” he asked. “Dave’s not coming back tonight.”
When I looked confused, he continued, “He had another date tonight, the jerk!” I was pissed, and ready to go home, but Fred was being very nice to me.
He took me to a nice pizza joint, surprisingly well-lit! (Dave only took me to dark joints!) Afterwards, we walked back to the dorm, his arm around my shoulders. It was the nicest date I’d ever been on!
Back in the room, he asked to see me naked. I was nervous, not knowing how much Dave had told him.
“Don’t be afraid,” he softly said. “I know.”
I turned my back to him as I shyly undressed. He whistled appreciatively when I turned around. Even though I have a small cock, I have small round breasts, wide hips, and a nice ass.
“I wouldn’t have believed it if I hadn’t seen for myself!” he exclaimed. “You’re very pretty.”
I smiled, flattered. Dave seldom compliments me. Some boyfriend he turned out to be!
I picked up my clothes and started to Dave’s room. Fred pulled me to him and kissed me. I felt wanted in his arms and didn’t refuse when he asked if I’d like to sleep with him. It was nice to be asked to bed instead of being expected to be in it.
His bed was small. We’d be close the entire night. I pulled the covers to my chin and smiled coyly. He slowly pulled the blanket back, exposing my trembling body.
Fred kissed his way slowly down my body, savoring my breasts. He licked my navel as if he were licking a pussy before moving down and kissing the hollows of my hips. He took my cock into his mouth and sucked me gently. (Dave only sucked me a couple of times and acted like he was doing me a special favor!)
He made face when I came in his mouth. He bravely swallowed it all. He turned me over and started to lick my ass, but quickly stopped. I hadn’t yet learned how to properly clean and prepare myself. I was pleased he tried, though.
I handed him my lube and he worked a couple of fingers into me while he kissed his way up my back. Shivers ran up and down my spine. He nuzzled my neck and whispered how pretty I was.
I expected him to crawl on top and push his cock in, but he surprised me and rolled me onto my back. He raised my legs slightly and slid into me. He pulled my legs and wrapped them around his legs. He taught me how to pull myself onto him and to match his thrusts. I wrapped my arms around him and kissed him while he slowly thrust into me.
I was used to being on my knees or on my stomach when someone fucked me. This was like a first time for me. The others just fucked me. Fred made gentle love to me. He treated me as if my desires and pleasure was just as important as his!
I surrendered to the feelings he stirred with his cock sliding in and out of my channel. I felt like a real woman in his arms, not like a boy pretending to be a girl! I’d never felt this good as a boy. His warm breath on my neck and ear pushed me to heights I’d never been.
I’d never come from someone fucking me before. I felt fantastic. I never wanted these feelings to stop. I smiled up at Fred as he continued thrusting in me.
Fred dumped his load into me and started to roll off. I held onto him and clenched my asshole on his cock several times and pulled myself onto his rapidly hardening cock. He started thrusting again.
I bit his lip lightly then said, “you can fuck me harder!”
He was soon fucking me as hard as he could. His thrusts were faster. I nibbled his neck and ear, whispering how good he felt inside me. His body ground against mine as that cock slid in and out. His breathing got louder and he growled as he emptied another load into me.
We fell asleep, him cuddled against my back.
The next morning, Fred kissed my cheek before leaving for early practice. I woke later and found a note. He thanked me for a wonderful night. He also left his phone number and said he’d like to see me again. I was fun and a really nice woman. (He called me a woman!!) He reminded me that he was in a relationship, but would still like to be friends, if I liked.
Since he was honest up front, I left him my number and asked him to call whenever he liked. I needed a friend like him.
Dave came in after I’d showered. Even though he was a jerk, I still wanted him to fuck me. I still had confused feelings towards him.
“I don’t do sloppy seconds,” he said, and went to his room.
Okay……I’m a slut in his eyes. My feelings died. I’d still fuck him if I was horny, but I’d no longer be at his beck and call.
The following weekend, he wanted to get with me. I told him I already had a date! (With Fred, as it so happened.)