I had my first M2M anal sex experience 18 years ago at 31, back when I had a waste line and abs. Lol. A bi/gay guy hit on me at the closing of a predominantly straight club one night. But as he left, he leaned close and whispered, āI will keep anything that happens entirely between usā. I smiled and said I was flattered, (which I actually was). I didnāt respond then but on my way out the door in the mob of non socially distancing people, he was next to me and grabbed my hand and put a napkin with a phone number in it. Evidently to the bold go the spoils, as I sat and thought on it that night. I picked up the phone, a day later, my voice cracking occasionally and called the number, Stephen answered. We talked, and I asked him if he was sincere about the level of discretion that he mentioned? He assured me he was and I agreed, with much nervousness, to come over to his place that night, where he assured me that we would have complete privacy.
I showed up, two stiff drinks later with a bottle of Grey Goose, and a lot of apprehension! He put me at ease quite easy as he was, not straight, but not effeminate. He told me he was a top, and then smirked at me bemused when he deduced that I didnāt know what the hell that was! He asked my fantasy and I told him I would like to receive anal as long as it wasnāt too excruciating. He said he could make it feel amazing. ( I had taken two 3 qt enemas before that afternoon just in case) The look on his face and the absolute confidence in his voice led me to believe he was telling the absolute truth... I flipped a switch in my mind and away we went. He went down on me for a few minutes( which to find out most tops donāt do) and then he asked me to please him... He was half or 3/4 hard already and huge, but I thought Iād try. āHere Is the worst head youāve probably ever hadā as I took him in my mouth. He enjoyed it, and he was rock hard and immense... Iām starting to have trepidation as the only thing Iāve had inside me prior were enema nozzles, and girlfriends fingers and one small is vibrator from a Dutch girl in an exchange program.
So he took charge, which I liked, and asked me to lay on my side. He spooned in behind but stared working Vaseline into me. Iām loving this and his fingers are thick so I am already panting a little. He then took out his thick 8 inches, ( I know/ ruined for life the first time out) and slowly pushed against the opening. It took a couple of minutes, and finally he said push out like a BM, and he shoved forward and got his German sized nazi helmet head in me... Wooof! It took the breath out but he was experienced, and didnāt budge it an inch, just let me pant and get used to it. He was just moving his hands and telling me how good I was doing. After I got used to it, he played the game, an inch at a time. He would almost pull all out but, on the in stroke, heād go deeper, eliciting a number of gasps from me. Finally when I felt literally like his cock was in my stomach, I felt his hips flush flat against mine. He left it all the way in for a minute or so and then proceeded to the slow in and out phase. I was in heaven! Completely full inside, with no pain but only pleasure thatās mounting by the minute.
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Weāve had a number of drinks together to soften the nerves, but itās had the effect of giving my friend the ability to fuck me as long as he wants, which he proceeds to do! 35 mins and two writhing, frothing anal orgasms on my part. I hav never an same sex experience could feel this good. I made a friend, but could never have Emotional or physical attraction to him.. totally doesnāt mean I didnāt LOVE the sex between us, I did. But couldnāt be in anything other than a physical relationship with a guy. I know that herse people that disagree on this sit, but Iām 49-50 and my opputunities are fading into the sunset. Iām not going to feel bad about them,,,