I’ve seen a lot of post regarding what anal sex feels like for a man. This is a wonderful topic. For me it seems like the experience of receiving anal sex from an experienced partner that you are very comfortable with truly rounds out your understanding of the sexual experience as a man. For me there is nothing comparable to anal sex. The experience is singularly unique and different from that which comes from “regular” sex. The only way to truly understand this is to take a dip in the pool. Here I attempt to will share as much of what my first experiences were like for me, though it is not possible to adequately capture the experiences in words.

I’m not going to get into a discussion of “how to”. There is plenty of information about the technical skills that are employed when making love anally. I will just mention some things as they come to mind so I can share my experience as fully as possible.

The very first time I had anal sex, the encounter was rather short. I was with a partner that really enjoyed oral sex with guys. He was married and seemed to be reserving the pleasure of fucking for love making with his wife. I told my partner of the time that I would really like to feel what it is like to have him inside of me. He said, “well OK, I didn’t know your were into that sort of thing.” Well this was an early experience with male to male love making, so I really wasn’t into anything in particular. I just wanted to experiment and gain an understanding of all the ways men can make love to each other. It felt to me that our oral encounters were just kind of brushing the surface.

So at this point, anal encounter number one was a go.

My partner suited up with a condom and I asked for some lube. We decided that I would ride on top of my partner, so he lied on his back and I positioned myself on top him so I could look into his eyes. I spent some time getting his penis thoroughly lubed up and, then I scooted forward so I could position myself better over his penis. Kind of squatting over his penis, I could feel the tip of his erection on my ass. I used my right hand to guide his penis toward my opening. I had a lot of lube on the tip of his penis which I used to lubricate myself as I started to work the head of his penis inside of me. It was kind of hard to get him in at first. I had to use the weight of my body to apply downward pressure as I held him firmly to guide him inside of me. Then all of the sudden, my ass seemed to relax just a bit and he slipped in. This was stunningly painful. The head of his penis was just inside of me and I froze in that position for a while. It took some time for me to get myself together and decide what to do next. I proceeded by continuing to slide him gently inside. I gradually made it all the way down, but as I did , I felt another strong sensation and without warning I lost control and began to come all over my partner’s belly. Breathless by this time, I sat motionless on my partners lower belly with his cock fully penetrating me. Again I was a bit stunned by the intense sensations, but by this point I was awash in the warm feelings of sexual satisfaction. As I regained control of my lower body, I began to gently rock my ass so I could feel my partners penis titillating me from the inside. I kind of fell into a bit of a trance as I rocked over my partner. I could have continued this for hours, but after a short time my partner told me that he didn’t feel like he could orgasm with me on top of him. I slowly dismounted and then finished him off with a passionate blow job. We were both quite content after we came, but we mutually decided that we were really in different places sexually. This was our last encounter. It was time for me to find a new sex partner.

Finding a sex partner that fits you nicely is a bit of a delicate art. I won’t go through the long process of finding my next sex partner here. Suffice it to say that I was successful. After going through the usual social exchanges that you have to go through to let another man know that you want to get naked with him, I managed to get an invite to my new sex partner’s home.

For my first meeting with my soon to be lover, I wanted to put on an outward appearance that would help define our sexual roles. I had no idea how my lover would respond to this. I just decided to take a chance, so I ordered some new bedroom attire for the occasion.

When I drove to my lover’s place, I was dressed only in my sexy new bedroom ware, which consisted of silky black hipster panties covered by a lacy white camisole and finished off with a pair of black bedroom slippers. The camisole was sized for a tall, slender woman with modest breasts, so my lacy top hugged my body nicely. The top was long enough to just cover my panties and to help accentuate my curves, I used a black velvet elastic band as a belt to pull the camisole in around the smallest part of my waist. This little get up was a real turn on for me.

I was incredibly horny driving to my lover’s place. I pulled up to his home and parked. The night air was very cool and there was a light mist in the air. The walk from my car to the front door of his home helped clear a blaze of sexual chatter that was clouding my head. I knocked on the door. My new lover answered and invited me in. He was dressed in a robe, boxer shorts and a tee. The first thing my lover did was greet me with a friendly“well look at you” followed up with a long tender hug. As we embraced, my lover’s hands slid gracefully down my sides until he reach my ass. He then pull me firmly towards him so I could feel his crotch against my own. He asked me if I’d like a drink. I asked for a scotch on the rocks.

We sat at his bar for a while talking to get to know each other better. Then I felt a hand land gently on my knee and slowly start working its way up the inside of my thigh. I felt a wave of chills inside of me as my lovers hand slid under the bottom of my camisole and landed on my panties. I was so horny that my cock was aching to escape from my panties. My lover asked me if I would like to go into his bedroom. I shook my head yes, and we were off to the bedroom.

When we got into the bedroom, we stood for a while embracing each other. We spent some time running our hands over each others bodies exploring. We pressed close together so we could feel each other growing firm. My lover slid his hands underneath my top. His finger tips reached the top of my panties and with a single graceful motion my panties slid over my hips, down my legs and onto the floor, leaving my ass exposed from underneath my top. I slipped off my lovers robe and then his boxers so I could kiss the tip of his penis. I then raised up, turned around and bent slightly forward, backing up until I could feel his erection between my legs and pressing firmly against my ass. My lover ran his hands up underneath my top again and started to gently massaged my chest. He gradually worked his hands down my body, across my belly, over my pubic area and on to my own erection. He fondled me and whispered that we should move over on to the bed. Without hesitation my lover took my hand and lead me over to his bed.

We landed in bed and I rolled on top where we could continue grinding our cocks together. We fondling each other for some time and eventually ended up lying on our sides in a way that allowed us to comfortably give each other oral sex. For me oral sex is always the precursor to intercourse. Not to disappoint, I soon felt a finger dancing around my anus. I felt chills of anticipation knowing that I would soon have a finger inside of me. My lover used his index finger and forefinger to work lubrication inside of me and to help warm my anus up for something a bit larger. My lover then motioned to me that we were moving on. We were going to fuck.

At this point I should have asked my partner to put on a condom, but I felt kind of entranced by what I was involved in. My whole body was buzzing with anticipation. I just rolled over onto my back and my lover positioned himself between my legs. I had never been in this position before. I felt so sexy. I could hardly contain my excitement. I raised my legs up and placed my ankles over my lovers shoulders so I could lift my ass to meet up with the warm hard penis that was eager to greet me. I asked my lover to be gentle and start out slowly. I knew I was in for some shockingly intense pain. I was fine with that since I had handled it before. What I didn’t want to happen was for me to slip directly into orgasm before we really had a chance to enjoy each other.

The feeling of one or two fingers inside of me, working lubrication around had become quite comfortable. I started feeling some nice tingly sensations as if I were being lightly tickled from the inside of me. The feeling made me eager to have my lover’s cock inside of me. I motioned with my ass in a way that suggested I was ready. My lover moved up closer to me, placed one hand on my belly while he used his other hand to guide his cock inside of me. I could feel the tip of his cock stretching me open little by little, more and more. I took a deep breath in anticipation of what was to happen next, but once again I was caught off guard by a sudden, very intense pain. My lover sensed something or perhaps I moaned, so he stopped to allowed me to relax. I soon was comfortably with the intensity of my feelings and nodded my head to let my lover know I was ready for more.

We started out very slowly. Any pain I was feeling began to evolve into feelings of pleasure. I guess we started out screwing in the sense that we were moving together in a slow circular motion. With each gyration I could feel my lovers cock thrusting inward and then retreating, inward and then retreating, inward and then retreating. The rhythm of what I was feeling was mesmerizing. My lovers cock had not penetrated very deep at this point and I was beginning to feel incredibly pleasant sensations. Warm fuzzy tingling feelings radiated from inside of me, down my thighs, up my back, across my belly. I needed more.

By this time we seemed to sense each others growing desires and the intensity of our fucking began to pickup in response. I felt my lover’s cock move deeper inside of me. I felt that incredibly intense sensation that I had felt the first time I had anal sex. That sensation had pushed me right over the edge to orgasm the first time I tried anything like this. I was in a bit of a crisis. I did not want to come now. I started breathing more deeply and matched my breathing to the rhythm of what I was feeling. The feelings in my body were shifting in waves starting with warm fuzzy tickling inside of me then following up with sharply intense feelings that all the mussels around my genital area about to spring into ejaculation. Controlling my breathing seemed to be just enough of a distraction to keep me from slipping into orgasm.

Now we had begun fucking in earnest. I could tell that my lover was beginning to move in response to his own pleasure. We were now in that wonderfully mystical state of copulation autopilot. No need to have a mind at all. Your body just knows what to do as if someone had scripted everything for you at the time of our birth.

There was so much to take in that my mental state seemed to evaporated into a fine mist. Seeing my body dressed in this sexy camisole, the sensation of my legs suspended in the air by lovers shoulders, feeling my head moving up and back on the mattress, the cool night air kissing my naked ass, the power of my man thrusting his cock inside of me, imagining that moment when my lover will releases all of his desire inside of me. I actually felt like I was high on something.

I began to caress my lovers chest and work my ass to complement his motions. In response my lover began to lightly stroke my cock. The tingly sensations emerging from my penis were just a bit much. I could tell that if we continued I would have an orgasm. I whispered “ I am going to come”. My lover said in a reassuring tone “good” and continued fucking me and stroking my cock. In just a few more moments I started to orgasm. Warm come ran down my cock, over my lovers hand and on to my belly. Mussels in by anus and belly convulsed as my come surged out of me. All the nerves in my ass and my genitals were singing. The intensity was again overwhelming. My lover slowed down and allowed me to complete my ejaculation. He used two fingers to glide some of my come around on my belly as if it were a blob of tanning oil. Then he gave me a look that told me he was prepared to ease himself out if I were over stimulated. I shook my head to let him know I was fine. In fact I was over stimulated, but I did not want him to go anywhere. I wanted to experience my lover releasing his come inside of me. I wanted to feel the mussels in his body shimmering in orgasm. We continued.

My lover began thrusting faster and harder. Soon I could tell he was ready to release. My lover groaned with pleasure, pressed his cock firmly inside of me. He held his cock tightly inside of me as he released all of his maleness into me. I expected I would feel my ass fill with his warm fluid, but being so overstimulated from my own orgasm, I couldn’t make out anything in particular. As my lovers orgasm ran its course, he bent down toward me and we kissed for the very first time. I felt another wave of tingling sensations inside of me as the kiss lingered and my lover’s cock begin to retreat out of me. I was absolutely satisfied.