Loading...Up until a few years ago, my sex life was very conservative and pretty boring; certainly nothing worthy of a story. I had been with several men and the sex was often enjoyable, but it always ended up being very predictable and in the end, very vanilla. That all changed when I met my present boyfriend, Mike. He is very good-looking and is nicely equipped but what really sets him apart is his ability to use what he has. He is very open, very creative, and has this ability to get me to try things I have never done or even thought about doing; and to really enjoy them.
Each time we got together, it was something new. I kept thinking he would run out of new ways to make me orgasm but he never did.
I had never had anal sex prior to meeting him. Several men had tried, but it always ended up being painful or just didn’t feel good. Even though Mike is as big or bigger than those guys, he somehow was able to show me just how incredible anal sex could be. But this story is not about him performing anal sex on me, rather me performing anal sex on him. It all started on his birthday two years ago. I asked him what I could do to pleasure him in a special way. I was surprised when he said he would like for me to use one of my vibrators on him. He very obviously enjoyed it and it turned me on a lot more than I anticipated.
From there, we worked our way up to me using a strap-on on him and this story is about one very special evening that occurred on his last birthday. We have several different dildos and vibrators that fit into the harness, all of which he bought and added to our collection. We also had wrist restraints and straps that we sometimes used to intensify the experience. But for this evening, I had added a new dildo and some leg restraints to surprise him. And I had made arrangements for the kids to stay at a friend’s house so that we would have my house to ourselves. He came over around 7:00 expecting to eat dinner which I was cooking but hadn’t finished yet. I informed him that I had several surprises for him on that night and that dinner would come later. I led him into the den and we began kissing passionately like we always do, our hands roaming and our clothes beginning to shed. I broke our kiss and told him the surprise would start here and told him to undress. As he freed his hard-on I almost forgot what I had planned because I wanted that beautiful cock inside of me right then and there. But I resisted. Once he was undressed I gently moved him to the coffee table and told him to kneel down. We have a very open and trusting relationship and instead of asking why, I could tell he was eager to see what I had in store for him.
I positioned him with his knees on the floor and his body lying across the coffee table. I put a couple of soft towels down to avoid knee burn since I planned on him being in this position for quite awhile. I noticed that the coffee table was actually a bit too low for him to rest comfortably on it so I grabbed several large books and propped up the end of the table that his stomach was resting on. In this position, his butt was sticking up in the air while his face was actually lower. As I was getting out the restraints, I noticed his cock was rock hard in anticipation. I love the sight of him bent over with his ass exposed and his balls and cock hanging down. I stretched his arms out above his head and attached the restraints to his wrist and then used straps to securing them to the legs of the coffee table. I sensed his surprise when I started placing the restraints on his legs but instead of apprehension, I notice his cock twitch in excitement. It took me a second to figure out the new straps but once I got them on, I secured them tightly to the legs of the coffee table so that he was now totally at my mercy. Once he was securely attached to the table, I informed him that he was mine until dinner and that he was not to talk until I informed him I was finished. I also told him that after dinner was finished, it would be his turn and he could do whatever he wanted to me. I’m not sure which I was looking forward to more.
At this point I just couldn’t resist and I got down on the floor and began hungrily licking and sucking on his tool. As good as it tasted, I had to stop, I didn’t want him coming too soon. I got up and finished removing my clothes and began putting on the harness. I’m pretty sure he already knew this was coming. Once I got the harness on I took out a very realistic looking 6’5″ vibrating dildo and slid it in and then tightened up the harness so that it would stay snug against my body. I’ve learned to enjoy the sight of my penis and the power it gives me, now I know why guys pay so much attention to theirs. I applied lube to the dildo and to his ass and I even gave his cock a few tugs for good measure. I turned on the vibrator and immediately began feeling the base of the dildo vibrating against my clit. I was getting turned on so I didn’t wasted any more time. I positioned myself behind him and slowly began pushing the vibrator into his ass. I can still remember the first time we did this and how surprised I was at how good this looked and how turned on I got watching the dildo as his anus opened up to receive it.
I continued to slowly push until it was buried into him completely and then I left it there for a few seconds while rotating my hips slightly to make sure he felt it. I was really getting turned on now and began moving back and forth, gradually increasing the intensity and speed of my thrusts. Each time my pelvis hit his ass I felt sensations rush through my body as the dildo continued to vibrate my clitoris. The combination of my thrusts, the vibrations, and the feeling of control that I had seeing him strapped to the table with his ass in the air had me approaching orgasm after only a few minutes and I really increased my thrusts. I climaxed after ten minutes or so and collapsed on top of him.
Now this is a pretty good story so far but we are just getting started. After resting on top of him for a minute or two, I got up to get ready for part two. Mike knew what was coming; we had done this part before. I reached into my bag and pulled out an 8″ dildo that was not only longer but thicker also. I replaced the smaller dildo with the new longer one and again admired how good I looked with this really nice package on me. This dildo was big enough to cause him some discomfort but he said that actually added to the intensity of the pleasure. But knowing this I did add some additional lube to help ease the dildo into him. I saw him wince at the thickness of my new cock as I began easing it into ass.
I really felt in control now and I loved watching as all 8″ slowly slid into him. I started off a little slower to give his ass a chance to get used to it but then I slowly began moving in and out of him. My own excitement began to build again and again I began thrusting into him. Each time I thrust into him he felt a twinge of pain to go along with the pleasure. He moaned each time my pelvis hit his ass and I knew this was both pain and intense pleasure. I had learned to enjoy this feeling of power and his moaning actually caused me to increase the speed and intensity of my thrusts again. At the same time my own pleasure began to mount. I could feel him occasionally attempt to move away from my thrusts but with his body securely attached to the coffee table there was really no place for him to go. Again this combination of sensations on my mind and body had me once again approaching orgasm. I slammed into him with force several times and then erupted into a very intense orgasm. As my orgasm climaxed I again collapsed on top of him.
Now usually at this point, I turn him over, push his legs up, and re-enter him while jacking off his rock-hard cock or sometimes when I am feeling especially flexible, actually taking his cock into my mouth. I am sure that is what he was expecting. As I pulled out of him and got up, I could see him relax and turn his head to look at me in anticipation of relief. When I made no motion towards the restraints but instead moved once again towards the bag, I could see his curiosity level perk up. He didn’t say anything because I had told him not to but his eyes stayed with me. I removed the dildo from the harness and then turned so that my back was too him. He couldn’t see what I was doing or what I had in store for him. You should have seen his expression when I turned around and there poking out of my harness was a 10.5″ dildo that was at least 30 percent thicker than the one I just removed from his ass. His whole body tensed as he tried to move against the restraints. He started to talk but I stopped him in mid-sentence and reminded him that he was not to talk until dinner. I informed him that I would go slow and that I knew his body well enough to know if the pain was too much and that he was too trust me. He murmured o.k., closed his eyes, and slumped against the table.
After generously applying more lube, I moved in behind him to get ready. It was at that moment that I thought he might be right, that thing was huge. I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn’t relaxing like he normally does but boy was this starting to look good. The site of that huge dildo slowly sliding into his ass got me going again. I held back though so as not to be to rough too soon. When I was about two-thirds of the way in, I felt his body react and a very guttural moan that I had not heard before escape his lips. He tried to pull away from me but there was no where for him to go. He turned his head and asked me to stop for a minute. I again reminded him not to talk but I honored his request and held up pushing for a few seconds.
He moved his ass around I suspect to attempt to change the angle a bit so as to relieve the pain and pressure. But when he did this the dildo naturally slipped into him further and he again let out a moan. At this point I must have had at least 8 or 9″ in. of this thick monster in him and my own pleasure began to mount once again. Without even thinking about it my body pushed into him so that the entire length of the dildo pushed into him and my pelvis pressed against his ass. He again let out a loud guttural moan as I pressed my body into him. I held it there for a second but then started moving slowly out an inch or two and then pushing back into him so that my pelvis hit his ass each time. I slipped into a slow rhythm moving a couple of inches in and out. Mike moaned constantly and I could tell he was in both pain and pleasure although I couldn’t tell which one was winning. As my own pleasure once again began to mount, I began to pull further out of him and thrust back into him. His moans and mine mixed as I approached orgasm. I reached my hand down to his cock and began stroking him as I thrust. Almost immediately he began coming even before my own orgasm climaxed. He moaned loudly and tried to move away from me as he climaxed but in my ecstasy I pressed into him deeply as my orgasm continued. Finally I collapsed on top of him with the dildo still buried inside of him. At this point he pleaded with me to pull out saying he was really really done and this time I obliged.
I removed the restraints and allowed him to recover for 30 minutes while I finished dinner. As we were eating dinner, he reminded me that after dinner, I was his and that what goes around, comes around. Uh oh, I hadn’t thought of that. But that’s another story.