What was your best Anal Experience?

Several of my ex gf's enjoyed using a strapon with me. My best one was the first time I had a strapon used on me. I was living in Southern California and was dating a very cute petite Filipino girl. We had been together several times and started to talk about some of our fantasies and I took a chance and asked her if she would fuck me with a strapon. To my relief she said she would love to as it would be her first time too.

We went to a sex store several towns away and got a nice strapon and a vibrator for her. She was so excited that on the way home she was dripping and hiked up her skirt and fucked herself with the vibrator until she came several times.

When we got home she got me ready by licking my ass and using one of my plugs on my ass. Finally she put on the strapon and had me on my hands and knees waiting for her thick strapon. She took her time and eased into my virgin ass until I could feel her stomach against my ass. It felt great and she was telling me how hot I looked with her cock in my ass.

After pounding me for about five minutes she had me role over and kept fucking me hard while kissing me until I came without touching myself. After that we had many times where she would fuck me with a strapon.

The last time she fucked me with a strapon was when she put a collar around my neck and tied me to the hotel balcony railing late at night and fucked me hard while a cute girl by the pool watched us. I miss the hot sex we had and still think about it often.
 
Several of my ex gf's enjoyed using a strapon with me. My best one was the first time I had a strapon used on me. I was living in Southern California and was dating a very cute petite Filipino girl. We had been together several times and started to talk about some of our fantasies and I took a chance and asked her if she would fuck me with a strapon. To my relief she said she would love to as it would be her first time too.

We went to a sex store several towns away and got a nice strapon and a vibrator for her. She was so excited that on the way home she was dripping and hiked up her skirt and fucked herself with the vibrator until she came several times.

When we got home she got me ready by licking my ass and using one of my plugs on my ass. Finally she put on the strapon and had me on my hands and knees waiting for her thick strapon. She took her time and eased into my virgin ass until I could feel her stomach against my ass. It felt great and she was telling me how hot I looked with her cock in my ass.

After pounding me for about five minutes she had me role over and kept fucking me hard while kissing me until I came without touching myself. After that we had many times where she would fuck me with a strapon.

The last time she fucked me with a strapon was when she put a collar around my neck and tied me to the hotel balcony railing late at night and fucked me hard while a cute girl by the pool watched us. I miss the hot sex we had and still think about it often.

Wow! That was so hot! Philipino women are gorgeous & you found an adventurous one! Thanks for sharing that exciting experience!
 
It has only happened a few times where I have allowed a guy to go bareback and then cum inside of me. I love the feeling of his cum slowly dripping out of my violated puckered hole.
 
I had received strap-ons several times and really enjoyed them. But then I became friends with a male doctor and over time we came to realize we both had bi-yearnings but neither one felt like we could share them with our wives. Anyway, one day we decided to get a hotel room and explore our desires. We were both so horny by the time we got there that we just stripped down naked, laid opposite from each other on the bed, and 69'ed each other to marvelous orgasms within 3 or 4 minutes. That took the initial urge off and let us relax a bit.

We drank a couple of beers while recovering and then he asked if I wanted to try anal. I suspected this was going to happen so I had totally cleaned myself out that morning in preparation. I said sure and he went over to his pants and pulled out a tube of lube. Laying flat on my back I pulled my legs up to my chest and spread them out as he started to open me up with his lubed finger. He got one finger all the way into me and stimulated my prostate, which that alone got me rock hard again. Being a doctor he knew exactly what he was doing. After getting me good and stimulated he opened me up more with a second and then a third finger.

Finally he got up on his knees and I saw he was rock hard again himself. He pulled my hips upward a bit, lined his cock up with my anal entrance, and then slowly slipped his throbbing, pulsating penis all the way into me. He had done such a good job getting me ready that there was absolutely no pain at all.

As he started fucking me his cock head would hit my prostate gland with each insertion giving me even more intense pleasure and making my own penis throb even harder. He knew it was my first time receiving anal from a real live cock and I think it made him all the more excited that he was taking my virginity.

He probably lasted 6 or 7 minutes before I saw his eyes close, his body tense, and his penis go all the way as deep as it could in me. I felt his cock spasming around my sphincter muscle and his cock head pulsating deep inside me as he started filling me with shot after shot after creamy juicy hot shot of his sperm and semen. It was so fantastic to realize that I'd finally done something I had fantasized about for so long.

Once he was done ejaculating he left his cock inside me and starting stroking my penis with one of his hands. As he did so he pumped his penis in and out of me slowly and I could feel the added wetness around it from his cum that was now inside me. Between that and all the stimulation my prostate gland had experienced I probably lasted less than a minute before he was milking a huge load of jism out of me. It spurted all over my stomach, chest, and even up to my face. It was absolutely amazing and totally satisfying in every way.

The only down side to the whole experience is once you've had a real live cum spewing cock inside you, nothing else ever compares to it again. ;)

Ay this made my pussy throb... FUCK!! :devil:
 
I had received strap-ons several times and really enjoyed them. But then I became friends with a male doctor and over time we came to realize we both had bi-yearnings but neither one felt like we could share them with our wives. Anyway, one day we decided to get a hotel room and explore our desires. We were both so horny by the time we got there that we just stripped down naked, laid opposite from each other on the bed, and 69'ed each other to marvelous orgasms within 3 or 4 minutes. That took the initial urge off and let us relax a bit.

We drank a couple of beers while recovering and then he asked if I wanted to try anal. I suspected this was going to happen so I had totally cleaned myself out that morning in preparation. I said sure and he went over to his pants and pulled out a tube of lube. Laying flat on my back I pulled my legs up to my chest and spread them out as he started to open me up with his lubed finger. He got one finger all the way into me and stimulated my prostate, which that alone got me rock hard again. Being a doctor he knew exactly what he was doing. After getting me good and stimulated he opened me up more with a second and then a third finger.

Finally he got up on his knees and I saw he was rock hard again himself. He pulled my hips upward a bit, lined his cock up with my anal entrance, and then slowly slipped his throbbing, pulsating penis all the way into me. He had done such a good job getting me ready that there was absolutely no pain at all.

As he started fucking me his cock head would hit my prostate gland with each insertion giving me even more intense pleasure and making my own penis throb even harder. He knew it was my first time receiving anal from a real live cock and I think it made him all the more excited that he was taking my virginity.

He probably lasted 6 or 7 minutes before I saw his eyes close, his body tense, and his penis go all the way as deep as it could in me. I felt his cock spasming around my sphincter muscle and his cock head pulsating deep inside me as he started filling me with shot after shot after creamy juicy hot shot of his sperm and semen. It was so fantastic to realize that I'd finally done something I had fantasized about for so long.

Once he was done ejaculating he left his cock inside me and starting stroking my penis with one of his hands. As he did so he pumped his penis in and out of me slowly and I could feel the added wetness around it from his cum that was now inside me. Between that and all the stimulation my prostate gland had experienced I probably lasted less than a minute before he was milking a huge load of jism out of me. It spurted all over my stomach, chest, and even up to my face. It was absolutely amazing and totally satisfying in every way.

The only down side to the whole experience is once you've had a real live cum spewing cock inside you, nothing else ever compares to it again. ;)

Amazing experience and I couldn't have said it better. The first time I bare backed was one of the best times of my life, feeling my boyfriend cum inside me, not pulling out or shooting inside a condom but actually unloading deep inside me. Going back to using condoms was never the same and dildos never felt quite as good. Taking two cocks at once was a real highlight, it took a while to work it and take both but it ended up pure ecstasy and something I will never forget.
 
Taking It Up The Bum...

In anal Porn-clips I love to watch the way the bottom's cock is lazily bouncing up and down to the rhythm that he's being fucked by. This is a source of endless fascination for me. It's delightful when that cock doing the sympathetic bouncing is your own too, of course… I'm a natural-born cock-sucker, that's what I prefer to do. But if the guy I happen to be with wants anal, that's fine, I can get off on that too, just so long as once he's done I get the jollies I deserve by going down on him and sucking his cock for a long self-indulgent session. I like it best when he doesn't cum up my tight little bum - there are no tastebuds up there! but pulls out before he does, so I get to savor all that spunk in my mouth. So ass-to-mouth..? yes, but strictly because that way I get my opportunity too...
 
I went for a massage, someone I had seen before. she started to give me a nice teasing massage, occasionally running her hands along my ass crack and then down my legs. slowly a finger ran around my quivering hole, then down my balls. she kept teasing and teasing before finally sliding up and well lubed finger into my waiting ass. she fucked me for a bit before asking me to flip over.

she continued with the sensual teasing massage getting me nice and hard. There was plenty of oil running down my cock by the time a finger returned to my ass, and then two. As she stroked my well lubed cock and fucked my ass i felt my orgasm approaching. She kept going and i shot my load over and on my head. She kept massaging my prostate as i came. DAMN that was a good time....get's me hard just thinking about it...hard to type more....
 
I went for a massage, someone I had seen before. she started to give me a nice teasing massage, occasionally running her hands along my ass crack and then down my legs. slowly a finger ran around my quivering hole, then down my balls. she kept teasing and teasing before finally sliding up and well lubed finger into my waiting ass. she fucked me for a bit before asking me to flip over.

she continued with the sensual teasing massage getting me nice and hard. There was plenty of oil running down my cock by the time a finger returned to my ass, and then two. As she stroked my well lubed cock and fucked my ass i felt my orgasm approaching. She kept going and i shot my load over and on my head. She kept massaging my prostate as i came. DAMN that was a good time....get's me hard just thinking about it...hard to type more....

wow that is a dream for me. would love that to happen
 
Several of my ex gf's enjoyed using a strapon with me. My best one was the first time I had a strapon used on me. I was living in Southern California and was dating a very cute petite Filipino girl. We had been together several times and started to talk about some of our fantasies and I took a chance and asked her if she would fuck me with a strapon. To my relief she said she would love to as it would be her first time too.

We went to a sex store several towns away and got a nice strapon and a vibrator for her. She was so excited that on the way home she was dripping and hiked up her skirt and fucked herself with the vibrator until she came several times.

When we got home she got me ready by licking my ass and using one of my plugs on my ass. Finally she put on the strapon and had me on my hands and knees waiting for her thick strapon. She took her time and eased into my virgin ass until I could feel her stomach against my ass. It felt great and she was telling me how hot I looked with her cock in my ass.

After pounding me for about five minutes she had me role over and kept fucking me hard while kissing me until I came without touching myself. After that we had many times where she would fuck me with a strapon.

The last time she fucked me with a strapon was when she put a collar around my neck and tied me to the hotel balcony railing late at night and fucked me hard while a cute girl by the pool watched us. I miss the hot sex we had and still think about it often.
WOW fantastic.
 
Vice Experience

Got a 10 minute head start again this session. I think I like that, gets me rolling and intensifies it when she starts sucking me. It is pure bliss. My prostate was like it was on fire!

She takes off her shirt to show me those beautiful breast and starts working me over the Vice.What I nice site to be looking down at.

She continues to tease me with her mouth and tongue. I'm getting really close so she pulls off and slides off her shorts. She goes to work on herself with her Rabbit.

New batteries so it is only a few minutes to orgasm for both of us.I came and came a huge amount. I feel emptied. :)

I feel sorry for the guys that don't know how euphoric this can be.Some will never know I guess. We talked about that during the session. She is a great lady!
 
A past gf fucked my ass with her finger. then a toy. all the while she talked dirty to me! She was fully dressed I was naked. There have been others sure but that one came to mind first!

KC
 
College Girlfriend

She didn't ask. She didn't hesitate. During foreplay, she just popped a finger up my ass and made me ride it. She said, "you're going to like this" before I had uttered more than heavy breathing. I was speechless the rest of the night. Sexual shock if you will. She was right. I loved it. Craved it since.
 
I went for a massage, someone I had seen before. she started to give me a nice teasing massage, occasionally running her hands along my ass crack and then down my legs. slowly a finger ran around my quivering hole, then down my balls. she kept teasing and teasing before finally sliding up and well lubed finger into my waiting ass. she fucked me for a bit before asking me to flip over.

she continued with the sensual teasing massage getting me nice and hard. There was plenty of oil running down my cock by the time a finger returned to my ass, and then two. As she stroked my well lubed cock and fucked my ass i felt my orgasm approaching. She kept going and i shot my load over and on my head. She kept massaging my prostate as i came. DAMN that was a good time....get's me hard just thinking about it...hard to type more....


God that sounds good. I'd lay back, raise my legs & enjoy
 
I went for a massage, someone I had seen before. she started to give me a nice teasing massage, occasionally running her hands along my ass crack and then down my legs. slowly a finger ran around my quivering hole, then down my balls. she kept teasing and teasing before finally sliding up and well lubed finger into my waiting ass. she fucked me for a bit before asking me to flip over.

she continued with the sensual teasing massage getting me nice and hard. There was plenty of oil running down my cock by the time a finger returned to my ass, and then two. As she stroked my well lubed cock and fucked my ass i felt my orgasm approaching. She kept going and i shot my load over and on my head. She kept massaging my prostate as i came. DAMN that was a good time....get's me hard just thinking about it...hard to type more....

Was this a professional masseuse?
 
Two Into One…?

Amazing experience and I couldn't have said it better. The first time I bare backed was one of the best times of my life, feeling my boyfriend cum inside me, not pulling out or shooting inside a condom but actually unloading deep inside me. Going back to using condoms was never the same and dildos never felt quite as good. Taking two cocks at once was a real highlight, it took a while to work it and take both but it ended up pure ecstasy and something I will never forget.

I'm almost wary of asking, Jakelc, afraid of appearing too prurient, but when you say you took two cocks at once… I wonder? I've been fucked anally by two generously-endowed gentlemen one after the other, which was an amazing experience. They took turns so that I was soon unable to even tell which cock it was sliding deep up into me. I've also, I shyly admit, been spit-roasted, with one big cock up my bum and the other throbbing and pulsing down my throat - after which they spun me around and switched points of entry. I was dizzy with joy. But I shrink from the idea of taking two cocks simultaneously up my tight little bottom! Is that what you mean…? Oh please tell me how you managed it, the idea is teasing and teasing at me in such a frightfully arousing way...
 
http://ecx.images-amazon.com/images/I/51bJozoM5AL._SY450_.jpg

Yesterday, wife was on the phone and told me to go get ready and wait for her in the bedroom.

I went to the bedroom and lubed up the You Too massager with virgin coconut oil. I slipped in in with no problem and set it to the lowest constant vibration. I slipped a cock ring onto the base of my shaft. The buzzing sensation felt really nice and I noticed the second vibrator was massaging the bottom of my scrotum. I began doing Kegels and the massager began to caress my prostate.

She continued on the phone so this went on for around fifteen minutes or so. I began to notice the massager began to move involuntarily and realized that the auto-fuck sensation is not just an Aneros thing, but a result of the muscle contractions once the prostate is sufficiently aroused. It seemed to stroke me on it's on. It caused me to buck and groan with pleasure. My cock was stiffening from the internal pleasures. I found myself on a level of pleasure that I have not yet experienced, even with the Vice.

She entered the room and I am in a state of euphoric sensations. She touches me and stroked my hardened cock. I growl with pleasure as she slips it into her wanting mouth. Words can not describe the pleasurable feelings this produced with the internal massage, the wet lips around me and the massaging of the scrotum.

She rolled over and began to pleasure herself with her Rabbit vibrator. I stroked myself and watch her as the massager continues to pump me vigorously. I increase the vibration to the next setting.I am so close to shooting as we share this erotic experience. I have to stop stroking as I am about to explode as I watch her enveloped in her own pleasure.

I grasp the base of my cock and feel the semen rising up the shaft on it's own. The pulsing massager seems to be pushing it higher and higher up my cock. She begins to moan and I explode with shot after shot of hot cum shooting up and landing on my stomach. I am bucking into the air on my shoulders and feet as the massager continues to buzz and I continue spraying hot cum.

This may be the best prostate ejaculation I have had to date. I highly recommend this massager to anyone looking to experience this kind of pleasure !
 
Never been fucked but I had an ex fwb that would have me kneel on the couch and she would lick my ass and jack me off . I would cum so quick . It felt so good
 
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