What was your best Anal Experience?

awired50 said:

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 !

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Love hearing your anal experiences with our toys & your wife. Had to share that one with my wife. Thank you for sharing the joy!

My best two were with the same man, on two different occasions. Both occasions began as our meets always did - with me showing up at his place and getting on my knees and deepthroating him, though not to completion. Then we went to his bed, and he positioned me cowgirl style, which I'd never tried before. He was well-endowed and as I basically sat on his cock, my weight driving it in, that was the first time he went into me all the way to the hilt - it was hugely arousing to feel his pubic hair against my ass. He just lay back and relaxed, so I started doing sort of sit-ups - he let me do all the work, not thrusting at all, which I found vaguely annoying - then he ordered me to stroke myself and pinch my nipples, my sub side really kicked in then and I became hugely aroused at being treated like a sex toy.
The other time, I started again by sucking his cock, and after he told me to get on my knees next to a large mirror he had in his room. he positioned himself on his knees right behind me, grabbed my hips and started pushing into me - I bent over, holding on to his thighs, pulling myself against his cock to make it go in deeper - the feelings of his cock thrusting in me, and feeling his muscular, hairy thighs was fantastic, but I nearly came when i glanced sideways and saw myself in the mirror in that position.

Best

My was when i was 17 up till then i had only slept with girls but my friend who is bi was always teling male on male sex is great and i should try it. One day i was horny so i decided to take him on his offer i went round his house we then got naked before i knew it i was on my knees sucking his dick until he came in my mouth then he rimmed me then he fucked me till we both came

Jenna2641 said:

Love hearing your anal experiences with our toys & your wife. Had to share that one with my wife. Thank you for sharing the joy!

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Thanks Jenna2641 !

Not sure where to start here but I had to chime in. Mary and I love anal . Love it tender, love it rough.
I've had anal sex with a man, it too was great!. Is the turn on the "taboo" or because it feels good. Both!

I am a male. I was with a couple. This was the first time I had anal sex. The lady was very petite. I was fucking her doggy style. My thumb was rubbing her asshole. Her husband and I had dp'd her earlier, me in her pussy and he in her ass. I pulled out of her pussy and put the head of my cock at the entrance of her ass and pressed in. As the head of my cock penetrated her; she kind of "mewed" no, no, no, and then literally impaled herself on my cock. Very erotic indeed.

w o w

michaelinteas said:

My best time was the first real cock I had inside me. I am a bi total bottom. I have a friend with benefits that I visit once a week and he is a very dominate top. one day when I showed up he told me that I would be taking care of his cock along with a friend of his. (My first threesome) . Up till that day I had only sucked his cock. After I had sucked them both to full hardness, my friend took my anal cherry while i continued to suck the other guy. Man it was soooo wonderful to feel him inside me with a cock in my mouth. Anyway, after my friend came. they spent the next three hours taking turns in my ass and in every position you could ever imagine until they could not fuck anymore.

does it get any better then that

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this sounds..... amazing my dick is staining in my jeans

OK my wife and her best friend wanted a FMF threesom I thought great .. But when it happened they both had strapons it was amazing I think the kink factor was off the charts but I had a great time..

Lucky you

The best I've had is an anal plug, which I enjoy. My wife won't fuck me with a strap-on and my chances of a real cock are very slim. Doesn't stop me thinking about it though.

Best time

My best time was with my Mrs, I brought her a strap on, well for me really.
She had me on my knees & lubed up in no time.
Gently at first she used her fingers, then pushed her cock slowly into me.
At first it was a little tight, but after a bit, I started to open up, even pushing back.
She really went for it then, fucking me real good, I hadn't even touched my cock, when I suddenly came,
Shooting all over the bed sheets.
I've tried a stick on the wall cock, I felt good, but never the same as my Mrs fucking me.
I can't ask her to often, she think I like that more than her lovely pussy.
I have got the urge to try a real cock one day though.

anal experience

My first anal sex experience was with another crossdresser, we were at a small party and were talking and she was playing with my ass you know just rubbing my ass cheeks and the she would slip her hand down my crack and it felt so good. So I kissed her and it went from there. So we went to another room and she had me lay on my back and she had a nice cock too so I sucked it for a few minutes and then she put my feet on her shoulders and went in very slow, then faster and after a few minutes I was begging for more and she really pounded me for about twenty minutes and came in my ass, after that I was hooked.

damn

this thread has got me so horny i want a big cock in my mouth and another just fucking the hell out of me. cumming on me from both ends.

mwm45 said:

this thread has got me so horny i want a big cock in my mouth and another just fucking the hell out of me. cumming on me from both ends.

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Glade i am meeting my fuck buddy today he is going to fuck me so hard

interwebs said:

Glade i am meeting my fuck buddy today he is going to fuck me so hard

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I'm jealous. but happy fir you

mwm45 said:

I'm jealous. but happy fir you

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he started as the person i experimented with in my teens but over the years we lost connect but he got back in contacted with me and asked me if i wanted to hook up and luckily my girlfriend and i have an open so i could have sex with him again

michelle3 said:

My first anal sex experience was with another crossdresser, we were at a small party and were talking and she was playing with my ass you know just rubbing my ass cheeks and the she would slip her hand down my crack and it felt so good. So I kissed her and it went from there. So we went to another room and she had me lay on my back and she had a nice cock too so I sucked it for a few minutes and then she put my feet on her shoulders and went in very slow, then faster and after a few minutes I was begging for more and she really pounded me for about twenty minutes and came in my ass, after that I was hooked.

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Oh wow, so sexy, would love to get fucked for the first time like this as well! Nothing like a fellow sissy gurl to drive you wild

got fucked by a guy who i though was straight recently turns out he is bi like me he is a top only it felt so great to have him inside me i was in my favourite postion, as well he was soo deep

My story

Getting fucked with long deep strokes leaned up against the cold van outside on a fall night

human_male said:

...I don't know why it felt so good that one time, but I'm sure the whole house must have heard me even over the noise of the shower.

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That matches my experience with dildos. A couple of times I made myself cum by just fucking them and without touching myself. But most times the experience falls short. So what's the magic ingredient?

Girlfriend and I had been playing in the afternoon, and we were engaging in some light anal play. Fingers and some rimming in between normal foreplay. Eventually we pulled out some toys and I started inserting a rather large (I think it's like 7-8" and pretty thick) dildo. When I had it fully inside me she quietly said: "I can't believe you fit the whole thing in there!"
Now I was rock hard and could see that she was definitely turned on by it, so I reached under the bed where I had hidden a surprise purchase. I pulled out a harness and asked if she wanted to fuck me. She told me to bend over the bed, so I obeyed and she slipped on the harness and attached the dildo. She took to it like a fish to water and I had to beg her to stop at one point because I was going to cum and wanted to prolong the feeling as long as possible.
And that was my best experience

TomBoner said:

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.

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THAT IS FUCKING HOT!

thinking about it my best time was when my boyfriend got me on all fours on the coffee table and used a dildo on me while his friends watched and then he and his friends used me hard , i came so hard and made such a mess on the coffee table , bliss.

Not the best but my first......

I knew i had a sexual attraction to guys before i met Doug but he was the first guy I let it actually happen. Before then i had been confused about my fantasies for guys. I knew i loved women. But had a desire to be with guys too. After i sucked Doug off i said good bye but knew I would see him at my favorite windsurfing spot the next day. I had been seeing him there for the last few weeks.

See him i did. And we started seeing each other day after day, we would go out together and i was oblivious to the stares ,from the girls i knew and the guys. I didn't care. Doug was hot and very nice. I was smitten. I sucked his cock several times in a couple of days and thought i was getting pretty good at it. One night after a movie Doug rented* a hotel room. He said he had a surprize for me. I was hoping but unsure. We were spooning in bed and i loved the feel of his hard body against mine. I could feel his cock hard against my back side. He was kissing my neck as i felt his finger rubbing my hole. Then he rolled me on my stomach and started licking my asshole. It felt so good. And then when i was good and wet i felt his finger slide in me. Luckily neither of us was touching my penis because i was ready to explode on the spot.

I was stroking Dougs cock while he licked and fingered me. I was amazed at how hard he was and i fairly shook with anticipation when he asked if he could fuck me. I wanted him to do anything he wanted to me. But that didn't alleviate my nervousness. He knew i was nervous and he kissed me and told me to trust him.

Out came the lube and he knelt over me , with me on my back and rubbed lube up and down my exposed hole. He generously fingered me with lots more lube making my chute slick and ready. Then he doused his glorious cock with more and rubbed it in slowly with a big smile on his face. He was beautiful right then cock in hand and the lust glowing in his eyes.

He leaned over me and kissed me while he rubbed his head up and down across my opening. His tongue and his cock were turning me on so much and then i felt him push gently but with constant pressure and he wispered in my ear to relax. Then i felt the sensation of his cock entering my hole. I want his hard cock inside of me ,i wanted to glide up and down on his shaft and feel him cumming inside of me. His engorged glans popped past my sphinctor and i made myself relax as he pushed on in. He kept going till his hips were pressed against the back of my thighs and he was fully inside of me. I felt gloriously full and didn't want to move. But he needed to and kissed me again as he started slowly puling back and pushing back in deep. I was so turned on and he could tell. In a moment i grabbed his hips and started pulling him into me. Grabbing his hard ass. I could tell he was getting more turned on and could feel him getting even deeper and harder. His pace quickened. And as he did my cock got even harder in his grip. I felt so good having him fuck my hole, i felt so turned on knowing he was getting more and more turned on. His tongue was playing with mine as i felt the pressure building and a huge wave washed over me as i pulsed over and over in his hand, my cum coating us and making my cock slippery in his grip. By the time i was done cumming he pulled out because he could tell i was very sensitive right then. And I lay there panting as he held me and kissed me.

Moments later* he got the best blow job of his life. I showed him as much appreciation as i could by letting him fuck my throat till i drained every drop of that delicious cum from his sexy balls.*

bluesky496 said:

thinking about it my best time was when my boyfriend got me on all fours on the coffee table and used a dildo on me while his friends watched and then he and his friends used me hard , i came so hard and made such a mess on the coffee table , bliss.

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This one kinda makes me jealous. I want that!

My wife dress in a nice little bustier and fucked my with her strap on. I came harder than I ever came before. I got her outfit dirty and covered my face.