Anal Pleasure for Him and Her
Introduction:
My story of discovering anal explorations and sharing it with a woman.
It started years ago, when I was in my early teens. One night I was lying on my side running my hands over my ass and in the crack and over my anus. I always was repulsed by the thought of male anal sex or even exploration that could lead to it, but curiosity got the best of me. I had taken a shower so my anus was clean, and I started prodding it with my finger. I had heard of rim jobs and a friend of mine said his girlfriend gave him one once and said it was awesome. But as my anus was dry I didn’t quite get much feeling pushing my finger around it. So I gathered some spit and stuck my finger in my mouth getting it all slicked up. I went back to prodding and started circling around my anus and wow! The tickling feeling immediately got me hard. Then I thought of women who liked getting fingered in the ass, as well as men, and wondered what it would be like. So I slowly started pushing my middle finger in. Immediately my anus locked around the tip and contracted a few times. I pulled it out then started to push it back in. This time it gripped and wouldn’t let go, suddenly convulsing on my finger like it was a mouth sucking on it. The feeling on the inside was amazing. My colon reacted to my finger contracting and releasing. It felt so sensitive on the inside touching my finger. After a minute the contractions stopped and my anus relaxed, so I decided to pull it out and push it back in. This time my anus relaxed a bit more and slickness inside my anus had lubed up my finger enough partially aided by the spit. I started pushing it in and out. The feeling was indescribable! My cock got partially hard so I grabbed it with my other hand and started stroking it. But something seemed lacking. I wasn’t getting the feeling I got when I stroked my cock, inside my ass. I always assumed the anus acted just like a vagina when penetrated. But nothing happened. I was getting excited naturally because this was something new I was experimenting with.
I decided perhaps one finger was not enough. So I pushed in my index finger getting it all slicked up, and then pushed both fingers in. It took a bit of work like one finger did, and suddenly my anus was reacting again, contracting. This didn’t last nearly as long but I immediately felt full, like I had to take a shit or was in the middle of doing so. There was also some pain that started as my anus was stretching wider than normal. I had learned about anal sex from porn tapes my dad kept, since in those days the internet did not exist. I knew the anus was a ring of muscle that needed to be stretched out in order to accommodate larger items. So I separated my fingers. Immediately the pain kicked in and I snapped my fingers back together. So for the next hour or so, I experimented with my two fingers. I then masturbated and came with them in my ass. That feeling was interesting. My anus contracted in a good way as I came.
I experimented more and more after that. After one particular messy experience, I soon realized I need to relieve myself before doing it. But even then it got messy, so one day I found an enema bag in our medicine closet. I read the instructions and it mentioned good for cleaning out the colon. So I started giving myself warm water enemas before anal play. After a while two fingers got boring, plus I was not getting much depth. I wondered if going deeper was the key to having an anal orgasm. The closest object to my two fingers I had was a large sized novelty tooth brush that had a hard plastic handle. The handle was about a foot in length, so I figured that solved the depth issue. I lubed it up with spit and slowly slid it in. It was very interesting, like taking a shit in reverse, but not quite. You know that absolute relief feeling you get when the shit comes out? It was that as I slid it out, then a filling feeling as it went in. I slowly pushed it deeper, and when it was about 5 inches in it stopped. I couldn’t believe that was as far as it would go. So I pushed harder, not knowing there was another sphincter ring inside. Suddenly it hurt as it pushed through that inner ring. But as I groaned I also pushed like I was pushing out a loaf, and in slid the handle much deeper. It got to a depth of about 8 inches when it stopped for good. I tried pushing it harder but the pain and immovability told me I had bottomed out. I rolled from my side to my back and it pushed the brush up to the top of my colon wall. It felt really good and I immediately started masturbating. It only took a few strokes and I started cumming. But the contractions of my sphincter muscles in my colon and anus locked onto the brush and pulled it in and out, rubbing the handle on my prostate, or so I learned later, which was the reason for such a hard orgasm. I came so hard the first rope of sperm rocketed out and over my head hitting the wall behind me. “Holy Shit!!!” I yelled, and groaned loudly. But soon the contractions were pulling the handle into my ass so hard it start hitting that wall deep in my colon causing a lot of pain, so I immediately grabbed the brush and pulled it out, causing my whole body to grip into a hard orgasm. I had stopped cumming but the orgasm had not fully subsided. I realized the next day that I had pulled stomach muscles from cumming so hard. Also I realized the handle was not totally smooth as one edge still had the line from where the plastic was pressed together. The grip that my anus had on it caused it to cut into the flesh a bit and I soon realized I was bleeding a bit. My ass was sore for several days afterward, not only from where my anus was cut but from the stretching of the muscles. It hurt to take a shit for a couple of days. I smoothed out the brush with sandpaper.
Years went on. I would occasionally revisit my novelty toothbrush, but I was afraid I might turn gay if I did it a lot. I was so naive in those days. Then the internet came along and along with it a lot of info. I learned men enjoying anal stimulation did not necessarily mean they were gay. I learned about the prostate gland, and what it did with stimulation through the anus. That was why I came so hard. I still enjoyed women and had a very healthy sexual appetite for them. I had no desire to be with a man, but I did have the desire to have my anus stimulated. Over some time I lost the toothbrush, so I had to start experimenting with similar objects. Meanwhile in my love life, I was afraid of telling any of my girlfriends about my fetish and none of them ever tried going there, even for a rim job. I didn’t want them to think I was way out there. The fear was they would tell my very anti-gay friends and I would be ridiculed.
Over the next several years, as I was learning on the net, and experimenting with dildos, various objects, and food items, I started seeing women and men using larger items, like various bottles, large fruit, large dildos, baseball bats, and more. I learned as long as I stretched my anus slowly I would not lose elasticity. So whenever I decided to do anal play, which I kept few and far in between, I would start with objects my ass would quickly accommodate, and then moved into larger items. I washed them and laid them out next to me. As I became accustomed to one size, and would toss it aside and go with the next size up. Finally one day I managed to get a bottle of beer inside. It filled me so full, and pushed hard on my prostate. I came so hard I was afraid I would break the bottle. I couldn’t get enough, but I could also not get past a beer bottle, as it would hurt too much trying to get anything larger in. I decided I would have to stretch more often in order to achieve more. It was at this time I had a bone condition in my hip joint that kept me from going out. I was gaining a lot of weight as well and did not have a girlfriend or any prospects since I couldn’t go out. I was tired of my hand, and decided to try one of those cyberskin vaginas. A new toy!! It was pretty close to the real thing. This was one of the most expensive ones that had a vagina and anus, so I could find out what that was like as well. I since discovered it isn’t as close as the vagina was though.
Anyway, I was not working so I had a lot of time to experiment. I finally managed to get in a soda can. It went all the way in, and felt so wild. I started masturbating then thought of the cyberskin vagina. I got it out lubed it up and propped it on a pillow. It was awkward moving around with that huge can in my ass, and it was always difficult getting and maintaining an erection most of the time. I figure it pushes on the veins supplying the blood to my cock. But once I got enough of an erection and pushed it into the vagina my erection filled up. It was amazing and the sloshing of the liquid in the can made a sort of vibration. I came really hard but the muscle rings surrounding the can gripped it and it started to feel like it would tear. I pushed the can out of my ass, and as my anus snapped shut behind it, it let the pressure off my prostate and the blood supply, and it felt like I emptied my balls completely. I came so much it was like I was pissing the contents of my bladder out. Thank god the vagina had a hole on the other end or the cum would have blown backwards. So I had an updated fetish. Large objects in my ass and fucking a vagina. I did this for a long time. Eventually I have moved up to even bigger objects. I can now manage a baseball bat easily and without pre-stretching with smaller objects. I can also push oranges and apples in as well. I eventually bought one of those close handed rubber fists, and can manage to fist my ass with it whenever I want. Years of training my ass has kept it loose, but has not taken away the strength of my anus, in case I can’t always make it to a toilet right away.
Large object insertion was never easy or comfortable when screwing the fake vagina, so I used smaller sized objects and even discovered the harder they vibrate the better the orgasm yet. I nearly passed out from one such session, because I came so hard. I started experimenting with depth as well, and although it was painful getting through the upper sphincter to the large intestine, I managed to slide a 17 inch double ended dildo all the way in. I can’t tell you how that feels. Partially like being constipated, but the full feeling that I have come to love.
Anyway I always wanted to move to the next level. A real woman. I wanted someone to actually fist me, and I wanted to have sex with her while something was in my ass.
After finally getting over my health issues, I finally made it back out into the world. I started hanging around fetish clubs, and that was when I met Heather. While we talked and got to know each other, I braved up and decided to tell her what my fetishes were. She told me she was really into anal play and wanted to do it to a guy, but none would ever go for it, or at least not past a finger or a rim job. I was excited, as was she, and we immediately headed for her house. On the way, I saw a sex shop, and had an idea. Since she like being fucked anally as well, and liked double penetration, I decided to try something. I bought the largest, longest double dildo they had. 23 inches long and almost 2 inches in diameter. Incidentally I can take more than 7 inches in diameter, but this would do for what I had in mind. More on that later.
We got in her house and started kissing and tearing each others clothes off as we headed for the bathroom. We had to get prepared, so she pulled out the enema bag. We took turns filling and draining our intestines until we were sure it would not get overly messy. We then showered each other, and playing with each other. We were so hot and horny I was scared I was going to cum in the shower. She actually did once, as paid attention to her pussy with a bar of soap. We got out of the shower and headed for the bedroom. I wanted to go first and let her have her way with me. I scrambled up on the bed onto my hands and knees. She pulled out a tub of anal lube she had in her nightstand and immediately lubed up her hand then my ass. I told her to go ahead and start with 3 fingers that I could handle it. Actually she had small hands so right away I told her to go for the fist. She immediately straightened out her fingers and pushed all four in till she got to her thumb. She stretched me by spreading her fingers and discovered I was loose enough, so she added her thumb and slowly slid her whole hand in. It was actually smaller than my rubber fist even when she made a fist, but this felt much different. It was warm it was soft and hard, and when she moved her fingers she pushed on my prostate which started the pre-cum flowing quickly. She started to pump her fist in and out of me slowly. It was incredible having this real fist in my ass and fully automated by her. I just had to kick back and relax sort of. After a few minutes my cock was hard as a rock and leaking pre-cum so much so that it made a puddle on her bed. I told her to go as deep as she could. Since she could bend her fingers she could easily get through the upper sphincter and into my intestine. She lubed up to her elbow and started pushing. It was a little uncomfortable, and her fingernail poked me once which made me wince in pain. But in no time her hand was in the lower part of my intestine, and she was up to her elbow. I looked at her upper arm, then back at her. She looked at me as she realized.
“Go for it!!” I said. She started pushing harder. Now my ass was stretching more, and it filled me more than I had ever been filled. She had to push so hard I moved back to the edge of the bed and she got on her feet to give her more leverage. I was stretching so much that my anus started spasming, and I was breathing really hard, as was Heather. Suddenly she slipped in a lot more as my anus stretched over her bicep and clamped down on her arm above that. Her entire arm all the way just below her shoulder was buried in my ass. There are no words to describe it. I was actually terrified for being at a place I had never gone before. We talked for a few minutes about how I felt and how she felt. She moved her hand around in my intestine, and I felt it. It was almost right below my left ribcage. It was amazing. The sensitivity was also pretty high, and apparently the intestine does not like to stretch as much as the colon, because I experienced pain like you would when you are really bloated or constipated. I told her to stop moving her hand, then got another idea and told her to flex her bicep trying not to bend her arm. When she did it put the appropriate pressure on my prostate and caused fluid to start flowing out of my cock. It was mostly pre-seminal fluid. But it felt amazing as it flowed out. I had a couple orgasmic spasms but it cause everything to clamp onto her arm and caused a lot of pain deep. I told her to back her arm out because it hurt. As she did so, the pressure relief felt absolutely amazing. Again think constipation, but that it finally starts moving out, and the relief you feel. She moved fast and pulled her arm all the way out, and I came. I came really hard and blew my load into her bed. Heather was in awe, and said “Oh my God!!” as she had never seen any man cum so much. She reached under me and used both hands to scoop up all the spunk lying on her sheets. I was still on my knees but had laid my head down on her pillow, my arms out to the sides. Heather showed me the huge handfuls of cum that she scooped up off the sheets, and then got a wicked look on her face. She stuck her tongue into the pool of cum and lapped up a large tongue full of it into her mouth, tasting it then swallowing. The rest she emptied into her right hand, closed her fist, pushed it into my ass, then opened it letting the cum run out of her hand and into my colon. She lathered the rest of her hand in the cum, and started sliding her hand in and out quickly closing into a fist as she went in, and opening it as she slid out. She pumped my ass like that roughly for several minutes. During that time, I got hard again.
I stopped Heather, and as she pulled her hand out I got up, pushed her onto the bed on her hands and knees. I reached over; got a large dab of anal lube, spread it on her ass pushing one finger inside. She moaned immediately. I pulled out and put some lube on my cock, and pressed it into her ass. She was tight. Very tight. It was obvious she did not stretch her anus like I did, but she still managed to take my 6 inches. I pushed until I was all the way in and stopped, letting her get used to the feeling. Her anus was spasming a bit and that feeling got me hard as a rock stretching her a bit more. Once the spasms ceased, I slowly started sliding out, which is what she was waiting for, she immediately started humming and ohhing. I reached under found her clit and started rubbing increasing the speed. Meanwhile I was pumping into her ass faster and faster. Heather really got vocal now, breathing heavier. I stuck my thumb into her vagina and rubbed her clit even harder. That was it, I felt the spray hit my hand as she came, her ass clamped on and off my cock milking it like crazy. I was not ready to cum yet since I had spilled more than my share earlier. As soon as she stopped spasming, I slid my cock out. I was not done yet. I leaned down and started licking her pussy lapping up all the juices that were flowing out. She tasted so good I pressed my face so hard into her ass my nose started to penetrate her anus. I had my tongue buried in her pussy drawing out her juices when she came again. Her anus poked out and it seemed was trying to pull my nose in. I had to pull away or suffocate but realized my nose being where it was had triggered her orgasm.
I got up and pulled out the double dildo while Heather fell over on her side recovering from her orgasm. She saw me getting the dildo and looked up at me inquisitively. I motioned for her to get up on her knees, and then laid down on my back grabbing for the lube. She got the idea and pushed it over. While I lubed one end she lubed the other, hands shaking in anticipation. I told her to push 12 inches of the dildo into my ass leaving the rest out. The dildo being smaller than what was in there previously, slid in quickly, soon she had the 12 inches in, a portion of it in my intestine. I grabbed the rest of it and bent it upwards. From the base of my cock to the tip was about 9 or 10 inches. With one hand I held the dildo up straight and with the other, grabbed my cock and held it up. Heather swung her leg over me and positioned her ass over the dildo since it was longer than my cock. She lowered her self down and I guided it into her ass. It was a little wider than my cock so it took her a few minutes to get used to it. She lowered down until she was just above the tip of my cock. From there she slowly started riding the dildo into her ass. As soon as it became comfortable for her, she moved forward, straightened herself, grabbed my cock and guided it into her pussy. She let her weight take over and pushed the dildo in her ass and my cock in her pussy deeper and deeper. This in turn caused two huge sensations in me, the feeling of her soft velvety pussy sliding over my cock, and the other end of the dildo pushing down into my ass. I reached under and held it still so no more would slide into me, so she could get almost as much of the dildo as I did. I was double penetrating her and she was penetrating me at the same time. Both of our eyes rolled back and we became lost in a lustful feeling neither of us have ever experienced. Well I had, but only with that fake vagina. The feeling here was better, more intense, hot as hell, and pulsating. Since this was really the only position we could be in and make this work, she started rocking back and forth. I lay still for a time letting the sensations get my cock rock hard. Then I started pushing upward as she pushed downward. She was fucking me as much as I was fucking her. We started speeding up. I could feel her juices heat up and flow down my cock and out all over my balls.
“Ohhhh mmmmm….mmmyyy GGGG Godddd!!!” she screamed as her orgasm hit her. Her pussy gripped my cock and her ass, the dildo, and pressed them together inside her body, I could feel the plastic veins of the dildo through her pussy. I could feel my balls begin to stir. But I knew I would still need to build up more. I started thrusting up at her as her orgasm started to subside but it triggered another and another repeatedly. She was cumming over and over slamming herself down on me, causing the dildo in my ass to slide in and out much faster. That was all it took and everything boiled up at once. The dildo at the right moment arced in my colon and the top side pushed on my prostate, triggering my orgasm. My cock blew its top harder than it did the first time. I did not think it possible. But I shot the first rope of cum into her so hard; she let out this low guttural scream that progress up into a high pitch. She came once again so hard her whole body shook. My whole body shook. We screamed out louder than either had ever done in the past.
Heather collapsed on me as soon as her orgasm subsided and we both passed out. I awoke an hour later, my cock was soft inside of her, and the dildo still deeply lodged inside our asses. I slowly rolled over onto my side and lay her onto her side, reached underneath of us and slowly started pulling the dildo out of both of us at the same time. As the dildo slid out of her, she moaned again, woke up took a huge breath and groaned it out in another orgasm. I couldn’t believe she was still that close to cumming even though she had fallen asleep. Her hot pussy juices coated my limp cock stirring it back to life. The dildo popped out of her then me. I tossed it to the side. I decided I was going to fuck her again, but just straight this time. But Heather had other plans. She reached back behind her into her nightstand and fumbled around. She brought out two thin vibrators and handed them to me. We were going to do all my fetishes in one night. This was going to be interesting. She rolled onto her back pulling my cock out. I got up between her legs and turned a vibrator on handing her the other one. There was already plenty of lube in her ass, so I slid the vibrator in until just the end stuck out. I lay down on her and guided my cock into her. I could feel the vibrator in her ass which got me to rock hard status immediately. As soon as I pushed all the way into her, she stopped me, reached around turned on the other vibrator and slid it into my ass. But she held on to it. The double vibration was incredible, vibrating my anus, her anus, my cock and her clit. She came again, and went into the rolling orgasms she had earlier. I slowly pumped into her as she held the vibrator in me pumping it in and out. The position I was in made my anus clamp down on the vibrator harder thus increasing the vibrations. I could feel my balls vibrate even, so I sped up my strokes. I started slamming hard into her making her moans escalate into a scream as I bottomed out in her pussy. Eventually she started screaming as she came over and over. Her pussy was spasming violently grabbing my cock and pressing the vibrator in her ass against it harder. She was squirting up at my stomach so much I thought she was pissing. I couldn’t stand it anymore and slammed into her and held it there. That was the maximum contact of the vibrators and it set off my orgasm. I saw stars as I came. The awesome feeling subsided into pure bliss as I passed out spraying what was left of the cum in my balls, deep into her pussy. She must have passed out as well. When I woke up 10 minutes later, I could still feel the vibrator in my ass. She had let go of it, and my anus had pulled it inside. I had to push hard to get something that small out. I managed to grab it, pulled it out and turned it off. My cock had softened up and slipped out of her, so I pushed myself up. I could hear the dull buzz of the other vibrator and spread her ass to grab it. But her ass had sucked the vibrator in as well. She was still out, and I didn’t want the vibrator to get stuck since she didn’t have the practiced muscles to squeeze it out, I wasn’t sure she could. I pushed two fingers in and felt the end of the vibrator, but it was in so tight I couldn’t get a grip on it. So I pushed two more in and was able to grab it. Her ass was stretched well enough to accommodate most of my hand. I decided that would be our next activity when we had recovered enough. I pushed everything off the bed, pulled Heather up close into my arms and fell asleep.
The next day we got up went out to eat, ate and drank a lot of water, since we needed sustenance. That night my own fantasy came true as I fisted her ass. Heather and I have become close and we frequently relieve each other’s anal fetishes. We have probably done everything anal stimulating that you can think of.
So guys if you are afraid you are going to become gay by pleasing yourself anally don’t worry. If you are attracted to men, then you are gay already. Anal play spans every sexual preference. But do take the proper precautions; make sure you are clean make sure you are careful. There are places on the web that will teach you about anal stimulation, toys, and anal sex.
