My most secret masturbation fantasy is rooted in real teenage boy experiences at age 15-16.
My friend Jon and I had sleepovers pretty often and usually masturbated together in our separate beds. No looking, no touching. We talked about girls (both had GFs but nothing too serious). On this particular summer weekend, our parents went away to a conference together and thought Jon and I would be safer if we both stayed at my house. We would have all day Saturday and most of Sunday with the house all to ourselves.
On Saturday we hung out at the community swimming pool until late afternoon and then came back to my house. I felt very sensuous in my bathing suit and tanned body. It Jon was not there, it would be automatic to go to my bedroom or the bathroom, strip my suit off, and beat off in front of the mirror. I always thought my dick and ass looked the sexiest when they were pure white aganst the dark tan line. My tanned legs and chest looked cool too when I was all naked. Jon must have had the same routine, because we both started hinting about it when we got inside. I had such a hard on in anticipation of getting naked and touching myself. I couldn't wait! The idea of being alone in the house, naked and beating off with another guy was extra exciting.
I was extremely anal erotic and had hinted of that in our previous masturbation talks. Jon was evidently gay-curious. Neither of us was gay, as far as I know to this day. Maybe one or both of us could have been bi-sexual, but I had no awareness of that concept at the time.
Jon got naked first and went looking in my medicine cabinet for the jar of Vaseline. (He knew where it was from our sleepovers.) I have to admit that seeing his bare body--his ass and his hard dick standing out very white against his tanned belly--added to my turn on. I rubbed my sun-sensitive nipples and kind of squirmed in my damp bathing suit, pressing my erect penis against the inner lining. When Jon got back with the Vaseline, he said "Take your suit off. I know you have a huge hard on." Then he said, "Take it off in front of the mirror, where you can watch yourself. That's what you do, isn't it!" Already I was feeling relaxed and like he could read my mind. Standing about five feet from the mirror and rubbing my nipples a few more times in anticipation, I pressed the waistband down over my ass and dick and stepped out of my suit as it fell to the floor. I stood there for the longest time rubbing my nipples and looking at my dick and ass in my mirror, as I always loved doing right before beating off. It felt good to see and be seen, which I had never experienced with another person before. Jon was already rubbing his penis a little, curiously watching me in the mirror.
I took the Vaseline from where he had set it down, put just a small dab on my two middle fingertips, and rubbed it into my nipples; my next step before touching my dick. Anticipation! (I think it was adding to Jon's anticipation too, although it was not calculated to provoke a response. It was for my own pleasure, only.)
Before I go on, I have to say it felt so incredibly free and sexual to be alone in the house, naked, talking casually, and getting ready to masturbate in front of another person.
Just then Jon said "Before you start, I want you to show me all the places in the house where you jack off (his term for it)." That sounded free and exciting, so I opened the bedroom door and led him to all of my places. I showed him how I stand in front of the bathroom sink and mirror, took him to my sister's room where I would go naked with a hard on and look through her dresser and nightstand for anything sexy or erotic. (Usually all I found were her panties or a girl magazine that might have some underwear or bathing suit ads. If I was lucky, I might find her Tampons and could look in the box and imagine one going up inside her little cunt or look at the insertion diagram. Yes, I could actually beat off to those things, horny and desperate as I was back then!).
I was really ready to beat off by then, but Jon said "Show me what you do on an extra-horny day. I bet you have those too." I said "Okay, but you have to show me all these things at your house too, you weird son of a bitch." I took him to my mom's bathroom, the linen closet where she kept her douche bag, and admitted that on extra-horny days I would go searching for that and then put the nozzle up my ass with Vaseline while I looked at myself in the mirror and stroked my dick. We left it there and went back to my room. As I walked through the door in front of Jon, I felt his hand run lightly over my bare ass, which sent an electric jolt through me. I think I must have visibly shuddered. MAN, I WAS SO READY TO BEAT OFF! I grabbed the Vaseline jar, took a big gob, and started. OHHHH, GODDDDD. What a feeling! I could feel his eyes on me, too.
It didn't take long to cum, first me and then Jon maybe a minute later. I caught his eyes watching my cum shoot out, and I certainly watched his. Felt a little silly after, but also very sexy in this highly-charged situation. We decided to stay naked in case we wanted do more later. We ate junk food, joked about nakedness and our bodies, called each other names like stupid, jack off, and dumb shit.It felt good even being in the kitchen naked with another person. Forbidden-like, and a little bit dangerous.
It was getting to be dusk by now and the dimming light in the house was making things feel even more private and tempting. Cozy, kind of. Jon was the first to get an erection again. Seeing him walking around with it sticking out and bouncing stirred something in my stomach. I knew it almost was time for something to happen again. Something sexual and naughty and hidden. I went into my bathroom and closed the door, standing in front of the sink rubbing my nipples and watching my penis get fully erect. In that private moment, I can clearly remember thinking "What do I really want to do now?" I felt I knew, but had no idea if or how it would happen. Filled with that mystery and desire, I opened the door and went to find Jon, who was in my bedroom looking at himself naked in the mirror. I caught him looking down and rubbing a drop of wetness from the little hole all around the head of his penis. This was his private moment and I loved catching him in it.
I took a deep breath and said "How do you want to do this?" (That was suggestive, I admit. Giving him an opening.) Still, his response shocked and surprised me. He responded by cupping my ass with one hand and saying "I think you should get fucked tonight." OMG, I felt my heart thump heavily! It was what I secretly wanted but could never admit to.
Not knowing what to say--and not wanting to let on--I said "What are you, a fucking pervert? You gotta be kidding, right? He said "Well yeah, maybe, but just see what it would look like. For kicks. We won't do anything. Just finish jacking off after."
I had stuck so many things up my ass while masturbating that you couldn't even believe it. My mom's roll-on deodorant bottle with the rounded cap, a carrot, a cucumber (had to be careful with the size of those!), the handle of a hairbrush, a marker. While not the biggest thing, the douche nozzle was my favorite because it was so off limits. A bare, hard dick was the ultimate forbidden fruit. My stomach knotted up just thinking of it! I felt my hard on throbbing and could almost feel the wetness oozing out of me. I looked at his dick in a different way now, I have to admit with some lusty desire. (Even though I was not gay and never would be.)
He said "You should bend over something." I wanted to, but definitely wanted to be persuaded and guided to it, suggestively. We looked around and talked about it. It needed to happen in front of a mirror, so we could both see what it looked like. (That was the whole point of it, right? Just to see it.) We went into the bathroom and talked about bending over the vanity. I did and he stood behind me. Couldn't see enough. Back to the bedroom. "You could lay over that chair," he said with his voice trembling a bit. "We could drag it over by the mirror." We dragged it over. I went to get a bath towel. First I put it over the big overstuffed arm of the chair and laid over that. I felt sexy and EXPOSED, like I could be seen and could actually be fucked in that position. There was an almost shameful feeling that I could not hide my secret desire very well. We both joked and swore a lot to cover the awkwardness. Finally we turned the chair 90 degrees and put the towel over the back of it and I bent over, all the while watching the erotic scene reflected back in the mirror.
My heart was pounding. It looked SO SEXUAL to see myself naked and laying over that chair, my ass reflected in the mirror, him behind me with an erection, stoking it lightly. I could see him looking at my ass and his dick. Again, I felt vulnerable and exposed...a delicious sexual soup of feelings! For a moment I thought let's turn the tables; see what it's like with you bending over and me behind you with a hard dick. Interrupting my thought, Jon said "We would need some Vaseline if I was really going to fuck you." I got up and watched myself with bobbing penis walk over to where the jar was and smear a big fingerful over my asshole, as I had done on every extra-horny day before. I rubbed more Vaseline into my nipples as I crossed the room to once again get into position.
When I was there, Jon moved in a little closer and said "How close do you think I should get?" I said "Just until we can see what it would look like, stupid." He stepped closer until his dick was an inch or so from my ass. He stopped and we both stared. In amazement, I still think to this very day.
After what seemed like minutes, I stood up and we both masturbated some. He reached around me and held my right ass cheek again, and I felt his touch surge into my balls and penis. After a breathless minute or so had passed, he asked "What would you really like?" I hesitated and said, with a very trembly voice, "Well, you already know I stick things in my ass sometimes. I guess I would like to just feel what it feels like touching my hole, just ready to go in. You want to see that too?" He said "Sure, why not?" (Himself apparently playing it cool now.)
Jon stood behind me while I stood straight up facing the mirror. I saw his hands come around in front of me and his middle fingers touching my nipples, just like he had seen me do to myself. (I never saw him do that to himself, btw, so I guessed that was only my thing.) It felt good, and I lightly held my dick in one hand. My heart was pounding harder and I could feel his dick just laying on the curve of my ass. It felt good. The whole scene looked--and felt--good.
He slowly nudged me back toward the chair. When it was time to bend over it, his hand on my back gently pressed me forward. Jon put both of his hands on my hips, with his fingers wrapping around the front of me. I could feel them; could see in the mirror. He was SO close to me now, barely an inch separating the tip of him from my bare, white ass. He said "What do you want now?" (Making me say it.) I was so full of lust that I had lost all resistance. "Just rub the tip of it lightly up and down my crack," I said, with my voice shaking hard and almost hoarse. That felt so good, so tempting.
"Now rub it up and down between my buns." OH GOD, another shock! His thighs were shaking from the excitement. I could feel the energy coming from his body. Hell, I could see his legs shaking in the mirror. His was voice was shaking too. My body was trembling almost violently. Now for the final scene...
"See if you can feel where my hole is and touch it there, just for a second." OH MY GOD, THE MOST ELECTRIC JOLT EVER! The thought that the head of his dick was touching my ass and could go in at any moment was tempting and thrilling beyond description. I said "Just press a little harder against me and then take it away." As soon as I felt the pressure, I reached behind me and pushed him away. Didn't want to be any more tempted. I told you, I am not gay. Just anal erotic.
We both masturbated, came, and flopped into our beds. There was no more joking that night; very little talk. Soon Jon was fast asleep. But I laid there for the longest time thinking...savouring...still trembling a little...trying to figure out how I felt about the whole episode.
That was Saturday night and we still had most of Sunday...home alone.