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Guys - tell about the first time being fucked

As a very experienced bottom in a relationship, I would like to offer you some practical advice. If you are on the same cock and it's not to big, that is one thing. But pain and crap are no fun.
First of all when in the shower get used to loosening your hole up using two to three fingers stacked.
Second of all, when going out on a date make sure you douche:
Use the women's nozzle with the holes along the side and fill the bag with warm water.
The put the bag on a towel rack or something by the toilet. Put in the nozzle and open the clip. Rotated it around in side and as you do, force the water out in to the pot. Don't go any higher than the length of the nozzle and do not try to hold the water. You don't want it coming out at the wrong time.
Do it three hours or so before you date, and be sure to lube it with silicon lube in case you are not in control of that - as least you will have some.
Bottom line, you never liked a dirty, smelly pussy. So make sure your boy pussy is nice an clean and lubed, and he can slip in without causing pain, and he will enjoy it more and won't have the after orgasm come down include shit on his dick..
 
JudyCD said:
First time I was on my hands and knees. It didn’t hurt but not as good as I expected. Later, I found if I was lying on my tummy with a pillow under my hips, it was as good as I hoped….better actually.
Click to expand...
Both can be fun
 
Clintdear said:
As a very experienced bottom in a relationship, I would like to offer you some practical advice. If you are on the same cock and it's not to big, that is one thing. But pain and crap are no fun.
First of all when in the shower get used to loosening your hole up using two to three fingers stacked.
Second of all, when going out on a date make sure you douche:
Use the women's nozzle with the holes along the side and fill the bag with warm water.
The put the bag on a towel rack or something by the toilet. Put in the nozzle and open the clip. Rotated it around in side and as you do, force the water out in to the pot. Don't go any higher than the length of the nozzle and do not try to hold the water. You don't want it coming out at the wrong time.
Do it three hours or so before you date, and be sure to lube it with silicon lube in case you are not in control of that - as least you will have some.
Bottom line, you never liked a dirty, smelly pussy. So make sure your boy pussy is nice an clean and lubed, and he can slip in without causing pain, and he will enjoy it more and won't have the after orgasm come down include shit on his dick..
Click to expand...
As you said, get used to loosen your hole every time you’re in the shower. First few times you may need real lube. Once you reach the point that you only need your soaped fingers to penetrate comfortable 2 fingers, the third will go in naturally. From there, you can be fingered with the natural oils your anus secrete. I still remember once I got fingered by surprise, and I had no problem to welcome the intruder, I knew I was ready to be fucked at any moment and any place. My anus got used to dilate when needed, even if lube and go slow was always good practice to avoid internal fistula…
 
Well it took some courage, but he wanted me as a girl as he knew I had lots of panties. I finally said fuck it and went for it....he didn't disappoint. It was amazing. He knew I wanted to and was patient in waiting for it. He came on my face and in me...loved it
 
A Grindr hookup in college. He was in his mid 20’s and we fucked in his bed that he said he shared with his GF. When he stuck his dick in me, I thought I was going to faint. It felt so good though. He breezed me and then I took his load as he shot on my face and onto the sheets. I think about that a lot.
 
At one time I had a gay boyfriend who - like me - was “middle aged” and had never been with a woman. We were lucky to be able to pass weekends together at his place most of the time or at hotels. He felt that intimacy and closeness did not require anal sex. One thing we liked was to frot in the missionary position until we came and one time after we had “got each other wet” I said that if he wanted to, I’d be open to having him see if he could penetrate me. He had about 8 inches and and “nicely” thick. Next time we hooked up he started to play with my hole with his fingers, and as I wanted him, I did relax down there. He and I got into the shower and while we made out he probed me with his soapy fingers to relax me more. We got out, dried off, and he “prepped” me with a Fleet’s enema. He laughed and said that He’d had it a long time and thought of it as just another type of condom but not one he could put in his wallet. Well, it worked fine. Condom and lots of lube, tension when his tip slipped past my sphincter and then just feeling full and really good. I was surprised that there was only some discomfort that happened before he made his characteristic sort of grunting sounds just before he came and before I felt him pulsing a few times. After he cam, he pulled out of me, took off the condom and emptied it on my stomach. We smeared it around over both of us and took another shower.
 
Gator50 said:
At one time I had a gay boyfriend who - like me - was “middle aged” and had never been with a woman. We were lucky to be able to pass weekends together at his place most of the time or at hotels. He felt that intimacy and closeness did not require anal sex. One thing we liked was to frot in the missionary position until we came and one time after we had “got each other wet” I said that if he wanted to, I’d be open to having him see if he could penetrate me. He had about 8 inches and and “nicely” thick. Next time we hooked up he started to play with my hole with his fingers, and as I wanted him, I did relax down there. He and I got into the shower and while we made out he probed me with his soapy fingers to relax me more. We got out, dried off, and he “prepped” me with a Fleet’s enema. He laughed and said that He’d had it a long time and thought of it as just another type of condom but not one he could put in his wallet. Well, it worked fine. Condom and lots of lube, tension when his tip slipped past my sphincter and then just feeling full and really good. I was surprised that there was only some discomfort that happened before he made his characteristic sort of grunting sounds just before he came and before I felt him pulsing a few times. After he cam, he pulled out of me, took off the condom and emptied it on my stomach. We smeared it around over both of us and took another shower.
Click to expand...
My goodness. What a hot story well told!
 
Wantstotryit said:
Well it took some courage, but he wanted me as a girl as he knew I had lots of panties. I finally said fuck it and went for it....he didn't disappoint. It was amazing. He knew I wanted to and was patient in waiting for it. He came on my face and in me...loved it
Click to expand...
Mmmm. Love panties myself!
 
My first time was with my former Dom. I had been seeing him for about a month. I was 19 and he was in his late 50s. He'd given me a dildo and plug and instructed me on how to use them and how to keep myself clean. One Saturday when I was going to see him, he told me to be cleaned out and wearing the plug when I got there. Obediently, I followed his directions and made my way to his house.

Once I arrived, there was our typical several minutes of small talk over a couple of beers before he had me strip down and handcuffed me to recieve a good spanking/whipping to set the tone and establish his dominance, as was our routine.

When he was satified that I had been sufficiently put in my place, he led my by the arm to his bedroom upstairs which was different than our sessions before. We'd always just played in the living room up until that point, so I suspected something different was going to happen.

Upon entrance to his room, he took off his robe and led me onto his bed. He then ordered me to suck his cock, which I did. As he began to get hard in my warm mouth, he started telling me that today was the day that I was finally going to get my cherry popped and how he had been looking forward to it. Abruptly, he pulled out of my mouth and shoved me further up the bed, face down, burying my face in the pillows. I felt him move in behind me and remove the plug I had in before smearing a generous amount of lube on and inside me with his thick fingers.

I found myself squirming against him as he readied me for the penetration that I longed for and he chuckled a little at me for being "a horny little slut". At last, he pulled me up to my knees, my wrists still cuffed and my face still buried in the pillows. He slowly guided his hard cock into me, working it in a little at a time until I felt his body against mine and I knew he had fully entered my ass. That's when he finally began to slowly push in and out, fucking me with his bare cock for the first time. The sensations were beyond what I expected and I moaned as loudly as I'd ever had during sex. Sensing how much I was enjoying it, he picked up his pace and began to pound his way into me while asking me how I liked getting fucked by a dirty old man.

I answered that I loved it and begged for more. Finally, he buried his shaft all the way inside me and came. Afterward, he had me roll over onto my back and jerk off while he watched and called me his "good little bitch".

That was the first time of many from him (and, eventually, his friend) that I had. We had many other adventures afterward and all of it was fun, but there was definitely something special about that first time.
 
tristantrotsky said:
Yes, anal does feel very very good…
It seems to me that most of us start out doing wary experimental oral with teenage – or maybe even pre-teen friends. That was me, I hold my hand up. I was there on my knees sucking my shoolfriends off long before we knew it was Gay, or whatever. It was just cock-fun. It’s only later, when you’ve become familiarized and acclimatized to just how good a cock feels in your mouth that you start to wonder how it would feel in other areas of penetration. Or at least, it was for me.
I was scared that anal would hurt. But by then I had an older mature friend I was sucking off on a regular basis. He showed me images of anal sex, and made it obvious that he wanted to fuck my bottom too. I was apprehensive. But I was even more scared that if I didn’t do what he wanted, in my mind he was such an attractive desirable man that he’d have no trouble going out and finding some other boy who would.
So I watched some videos. Read up some about anal sex. And lubed ready for him.
He took me raw naked bare-back doggy-style, I forced myself to relax my anal muscles and allow him access… and OH FUCK!!!!!…. you can’t possibly imagine just how amazing it felt as he slithered that big cock inch by inch up my arse. It made me gasp and whimper with pleasure, my own dangling cock was so hard it was aching, and when he started fucking me so that his balls were swaying and knocking up against my own balls it almost sent me over the edge. In fact… I ejaculated before he did, much to his amusement.
Once he’s cum deep inside me, and slipped out, I was like some besotted girl kissing, licking and sucking that big messy cock which had given me so much pleasure, groaning out my thanks and grateful adoration to the man who’d taken my anal cherry.
Needless to say we did it again on numerous occasions… and then I was fucked by other guys too, naturally… but I was always grateful to him for showing me the way...
Click to expand...
Such a beautiful, touching and passionate description of that powerful first fuck! How I love your ability to share the depth of ecstasy you experience with the men you embraced and with whom you gave yourself. I can feel your pleasure and it brings back my own first time experiences!
 
My first time being anally penetrated was not so great. I met a guy at his condo after chatting with him online. We got naked on his bed and he sucked me for a while. I was nervous and didn't get really hard but he put a condom on me and pushed me into his ass while I lay on my back and he straddled me. It was OK, but not fantastic. I think the chemistry was not there and, as I said, I was nervous. Then he told me go get on my knees doggy style so he could enter me.

There was no rimming or slow prepping of the ass, so when he put his dick in my ass, it hurt like hell and I told him stop. I couldn't do it. That kind of pain is not fun.

He stopped and I don't even remember if either of us came after that. It was a long time ago.

What I really need is a guy with a thin cock and small cock head, a bottle of poppers, and a slow buildup that includes lots of sucking and anal play where my sphincter is gradually stretched with fingers or toys until it is ready. Then the big moment when I suck him to make sure he is really hard and I lie on my back with my legs around his shoulders so I can watch him as he puts his cock inside me.

Now if you want to put a cherry on top of this fantasy, his wife is there the whole time kissing me, stroking my face, and offering encouragement while her husband preps me for this first real anal encounter and finally penetrates my ass. Now that would be the first anal I would really like to experience.
 
I had been with my first guy for about a month. Up to then we had just sucked each other and done a little ass fingering while we were sucking each others cock. I had spent the night and we woke up snuggling and kissing like a lazy cool Saturday morning. It was amazing, the kissing got more powerful and his cock felt harder than ever! He whispered in my ear “baby roll over” I didn’t hesitate and did as he wanted, he spent some time playing with my asshole and applying generous amounts of lube. He said “get up on all fours” and so I again did what he wanted. Then I felt his tip pressing against my ass! I fell to my elbows and that’s when it happened, he pressed though and was deep in my ass. It was so amazing and a feeling I still desire today. It seemed to last all morning and when he finally came we both collapsed on the bed and kissed madly and went back to sleep. 2 hours later we woke up and did it again and again!
 
Gator50 said:
At one time I had a gay boyfriend who - like me - was “middle aged” and had never been with a woman. We were lucky to be able to pass weekends together at his place most of the time or at hotels. He felt that intimacy and closeness did not require anal sex. One thing we liked was to frot in the missionary position until we came and one time after we had “got each other wet” I said that if he wanted to, I’d be open to having him see if he could penetrate me. He had about 8 inches and and “nicely” thick. Next time we hooked up he started to play with my hole with his fingers, and as I wanted him, I did relax down there. He and I got into the shower and while we made out he probed me with his soapy fingers to relax me more. We got out, dried off, and he “prepped” me with a Fleet’s enema. He laughed and said that He’d had it a long time and thought of it as just another type of condom but not one he could put in his wallet. Well, it worked fine. Condom and lots of lube, tension when his tip slipped past my sphincter and then just feeling full and really good. I was surprised that there was only some discomfort that happened before he made his characteristic sort of grunting sounds just before he came and before I felt him pulsing a few times. After he cam, he pulled out of me, took off the condom and emptied it on my stomach. We smeared it around over both of us and took another shower.
Click to expand...
Very nice
 
Wanking_Frank said:
You will like it, guaranteed. Getting in takes a little bit, but like I suspected it’s so much better than toys. Feeling the thrusts just brings it to a whole new level. I kept begging for harder even though he was doing the best he could. He used a rubber so I didn’t getthe full experience getting a load of cum in my ass but there was a satisfying loose feeling I had that stayed for a day or two.
Click to expand...
Yeah, the rubber diminishes the deeper feeling of the cock sliding in and out . . . .
 
Escierto said:
And?
Click to expand...
Oh sorry. I laid over the console and let her grease my hole. I remember noticing the full weight of another body on my back for the first time, the thought of being in the submissive position, unable to see what was going on behind me. I was filled with the desire to be taken. She pushed her small cockhead up against my ass. I winced and caught a wave of pain radiate from my ass. She ignored my pouting and kept pushing. I said “It hurts.” She responded “aww it ain’t that big. Shut the fuck up.” I kept quiet as best as I could. Immediately after the head got passed my anal ring, it felt good. I was getting pushed into. It was sexy. I felt full and submissive. The responsibility of pleasing someone was lifted off of my shoulders. I allowed my self to just be pleased and that was pleasure for her in and of itself. Sexy shit. She came somewhat quickly after about 10 minutes. It was a fantastic intro into the world of being someones pleasure hole. I loved it.
 
KinkStevens said:
Oh sorry. I laid over the console and let her grease my hole. I remember noticing the full weight of another body on my back for the first time, the thought of being in the submissive position, unable to see what was going on behind me. I was filled with the desire to be taken. She pushed her small cockhead up against my ass. I winced and caught a wave of pain radiate from my ass. She ignored my pouting and kept pushing. I said “It hurts.” She responded “aww it ain’t that big. Shut the fuck up.” I kept quiet as best as I could. Immediately after the head got passed my anal ring, it felt good. I was getting pushed into. It was sexy. I felt full and submissive. The responsibility of pleasing someone was lifted off of my shoulders. I allowed my self to just be pleased and that was pleasure for her in and of itself. Sexy shit. She came somewhat quickly after about 10 minutes. It was a fantastic intro into the world of being someones pleasure hole. I loved it.
Click to expand...
Good story. Similar to my own initiation by a woman with a small cock.
 
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