I told him when I hired him, eventually he would ask me to fuck him, and I would.

He was 17, bright, out of college at that age already. He was doing grad work and wanted a job. He was bright, honest, hardworking and quite feminine in his actions and appearance. He was 5ft. 8 in tall, thin, with a waist smaller than his chest and hips. He had long hair for a guy, down past his ears. He was a natural blonde, with a decidedly feminine facial structure too. His lips were naturally full and looked like they were made for wrapping around my cock. I like women and men who are thin, and feminine in appearance. Lars was his name, he sat in my office after going through all the interviews with others in the company. I was looking for a part time assistant. I had two full timers, and the part time gig worked with his graduate work. It paid well, very well actually. In talking to him I asked him about going through school so early and in talking about that, I gathered he'd never had a girlfriend. I asked "or boyfriend?". His answer was that he wanted a GIRLfriend but never had time for social interaction and being in college, now grad school at such a young age and not able to go into bars, it didn't lend him much in the way of options for getting a girlfriend. "Do you want the job, no matter what?" I asked him. He said he did. "Well one thing may change your mind" I told him. He didnt' think it would since the money was way more than most people made full time.

So I gave it to him straight. "You have the job, but I will tell you one thing which is sure. YOU will ASK me to fuck you at some point in time". He was shocked, "You're gay?" he asked and I told him bi, that I preferred women, but did at times take my sex with males, decidedly feminine looking, and acting males. "But I'm not gay . . . or bi" he stated. I told him "It doesn't matter, at some point you will want me to fuck you and I will ". Fast forward 6 months. We've been working together a lot, he mainly would take on his duties with me in the afternoon and evenings. We had several meals together taking him to nice restaurants, being driven home by our car and driver. He was getting used to the good life. At the beach house for a week, mixed work and relaxation. I finally got him where I wanted him. After a trip to the beach, followed by a trip to the nude beach, we had some drinks, and at the beach I saw his cock harden. It wasn't big, about 5 inches maybe six hard, and thin, only about an inch thick. He was trying to cover it up and I took off the towel and moved his hands. "Don't worry about it, it happens a lot around here" I told him. On the way to the water I pointed out several men with hard cocks, some jacking themselves with sun screen, others being jacked by other men, some by other women. He was hard as a diamond. We talked about the women, their bodies and how hot they looked. Even on the walk back to the house he was hard. At the sign we put on our swimsuits and went further to the house. Inside the house, I took mine off again and told him to do the same. Served another drink or two, gave him some muscle relaxers. I took some lotion and laid him down and jacked him. "Did you like seeing all those tits and pussies? Those hot assed girls and women?" he did say yes and even said how good it was making him feel with my hand on his cock. "You like that don't you?" YES was his answer. "Which girl are you thinking about?" He talked to one older woman, with the most perfect breasts and a hard firm ass. I noticed her too, perfect ass I told him. "Yeah it was" he said. "it's just like yours" I told him. "You think so?" He asked.

I told him I knew it was, but his was probably a lot firmer. He rolled over on his side. My hand still wanking his cock. I took my finger and pressed into his ass. He started to protest then stopped "No, don't, no . . . aaahhh" he was moaning as my finger did it's work on his prostate. I was lying beside him whispered to him. "You're getting harder, do you like that feeling, having your prostate massaged while your cock is being stroked?" He had to agree of course he was now pushing his ass back and forth pushing his cock in and out of my hand around it, at the same time my cock up against his firm, ripe ass. I pulled my finger out and moved my cock up to his ass. The lubed head at his hole, his ripe, firm, virgin hole. He moved back into me the head going just a bit between his pucker. "No" I told him. Slowing down my action on his cock, he bucked into me again. "No, I told you before you have to tell me what you want". He grabbed my hand and held it on his cock pushing in and out. My cock now no longer at his hole it was up against his ass crack. He kept pushing back on me. I moved my hand away from his cock and he begged me not to stop. "Then ask me what you want " I told him. He responded "I want your hand on me in front, and I want you to put your . . . your . . . inside me". He just wouldn't say he wanted my cock so I made him say it. "I want you to put your cock inside my ass, and use your hand on me, on my cock". "I will do it Lars, I will put my cock inside your ass, I will fuck you and I will jack your cock and make you feel good, but I told you the first day we met, you have to ask me for it." He reached back and pulled my 7 inch, thick cock, my tapered head now at his virgin hole. He tried to push back and get it in him but I pulled back too. "Tell me what you want, ask me to do what you want me to do to you" I told him.

"Fuck me, will you please fuck me and jack me while you do it?" he finally asked me. I moved his had from my cock and pushed it to his hole. "Are you really a virgin back here?" YES, "Is your cock a virgin too, never fucked anyone, girl or boy?" I asked. "NO, never, never anyone, this is my first time, please fuck me, will you fuck me please, please?". I held my cock as I pushed in slowly, he was moaning for it. I've had virgin asses before, male and female and never had anyone want it this bad. Once I was all the way inside him I grabbed his cock again. I didn't move my cock in him, rather he started moving his ass so it went up and down on my cock, and my hand served to jack him. When I knew he was close I used my hand faster and faster as I shot off all over the cushions of the couch. He was exhausted, but I turned him over on his stomach and started fucking in earnest. I only lasted another 10 minutes but he was loving all of it, groaning, grunting, moaning he was loving getting fucked. I pushed in and shot a big load in so many ropes. "Oh god, I feel it, I feel your cum shooting inside me it's so hot and wet, I feel it" he was practically yelling it out. "Is it good baby?" I asked "YESSSSSssssssss"

Then we were done. He stayed naked all the time we were in the house. By the fourth day, I took him out and bought him some panties, stockings and heels to wear for me. We were sleeping naked together I was fucking him many times a night, and even sucked his cock which then was reciprocated by him to me. He loved cum, he loved swallowing it, loved getting fucked. I had an older woman I knew who was into kinky shit like him. He got fucked while she sucked his cock, then after some recoup time (not much at his age) he fucked the 55 year old woman. He got his first piece of pussy, I even had her roll over so he could fuck her ass. I took sloppy seconds on her ass. Then she left and once again I had my little girly boy.