This is a long story, but it covers 3 visits and one of the best experiences I ever had.
Part 1
It was a sleepless Covid Sunday morning. I checked my messages, it was around 3 am. I was looking to play, but hell, who as gonna with Covid happening? The night was sleepy and it didn’t look like I would have any fun at all this time around.
Then my app started to light up. A guy inviting me to come and visit with him and his girl and have a threesome. And, at the exact same time, a lady asking me to join her and her boyfriend for a threesome. 2 separate couples asking me to come play right now. I started playful conversations with them, but both were adamant I come right now. As it turns out, the lady said “you’re speaking with my boyfriend on the other window. Comer over and play, set it up with him.”
He told me his name was Kim and he was a cross dresser, they were looking for someone to come over and play with both of them, she wanted to be pleased orally and fingered, he wanted to see where it all went. Not needing to be told twice, I got in the car and went right over, arriving shortly after 4 am.
He introduced a buxom 30 something large breasted lady – Kimmy – and we all got on the bed, large, luxurious and plenty of pillows. Black lights running, the lingerie reflected with it and it made socks on even a little sexy. He had a very sexy outfit on, and had a tight body to boot. He suggested I get naked, and in 15 seconds I was bare. The low lit room smelled of vanilla and was very delicious.
He asked what I wanted to do and I told him I wanted to eat her pussy, which is always a favourite of mine. She agreed and let me jump right in. I took her panties off of her and smelled them with her watching me. I could tell she liked the fact I got into that. I got my face down to in between her thighs. She smelled clean and fresh and was very very wet. My tongue traced her thighs and she pulled slightly at my hair, drawing me towards her pussy. While I normally love to explore and tease, this was not that kind of meeting. I clamped my mouth on her pussy full force and started sucking on her, sliding my tongue in and out, sucking on her hard and feeling her pussy juices dripping own my face. I could feel a fumbling around my crotch and feel him take me in his mouth. He was extremely talented and had a move that took me down to the base and pushed against his throat, feeling like it was a deep suction and the same time feeling like I was fucking his face. I could not help but moan in pleasure, to which he giggled – with him mouth full.
He enjoyed this for what felt like hours but was closer to about a half hour, and I felt him slide off. I kept eating her pussy, now she was asking me to put my fingers into her. I happily complied, her getting wetter by the second. I felt an unmistakable sensation of a condom being rolled on to me and felt him get on me, reverse cowgirl, and start to hammer into my stomach. He was tight and it felt amazing, she and I were speeding up and she just stopped to watch for a while. Kim wore lingerie, and kept a silky thong on at all times that I felt slipping against me when I went in and out, a sensation I absolutely love. Kim came back to my face and intentionally sat on it, sliding her pussy all over and letting me get a faceful of her and letting her juices run all over. I kept playing with her pussy with my fingers, now knowing she loved this.
She slid off and commented she needed to go clean up – we’d been playing about 2 hours at this point. He got up and on the bed, doggystyle and asked me to just fuck him hard, which I happily complied with. I had brought lubricant and it was coming in very handy indeed. Slow, fast, all combinations with him tightening his muscles. It’s a good reason why sex with a male is so different than a female. Kimmy came back in the room and commented she wanted to get that as well, but not today, since she had to go to work. We all sort of just wound down and I had not cum yet. The experience was phenomenal, I hoped I might be invited back. She got dressed, and we walked out to our separate cars, 7 in the morning to birds awakening and the day starting.
Part 2
At 7 pm that evening I received a message from Kim. Was I avaialble to come out and play?? I said I was, and he asked for me to come over as soon as I could. I had just been doing something, so told him I would be there as soon as I could. And I got there at 8:30. As I was coming in me messaged me and told me we’d be alone and asked me if that was OK. I said it would be, and knew I was in for something fun.
I arrived and he took me into his bedroom. I told him I wasn’t sure he’d ask me back, and he told me cattily “you changed my world – see?” and showed me he’d reoriented his bed. Oddly funny. He asked me what I wanted to do, I told him I wanted to have some real fun with him. He asked me if I wanted to do it bare or wrapped, I told him I preferred bare but it was early stages for that with him. He showed me a test result showing me he was HIV- and I had already done the same, so we were pretty comfy with whatever right off. He misted his room with the vanilla scent I associated with his place now. And himself.
He turned around with his ass in my face and started to take a drink. His is a small, bubble type girl’s butt and looked delicious. And he was completely hairless. I could not help but pull his peach thong aside and lick his asshole. Clean and delicious. I started to lick it more, getting it wet and then just grabbed his ass, pulling it into my face and started sucking on it, stuffing, my tongue in and out and eating his ass like it was a pussy. He gasped and I could tell he clearly was in love with the sensation. I did this with him for nearly a half hour, exploring him and loosening him up.
He stopped and told me to sit in an armchair. But stopped suddenly and asked me to put on a peach thong like his that had the crotch removed so I stuck out. What the hell. It smelled of vanilla and was a huge turn on. I sat on the chair and he immediately took my cock all the way down and sucked viciously hard, and it was a very hard to control sensation it was so dreamy. He was giggling at my reaction, which was a truly appreciative reaction just from the intensity.
He got up and asked me to put a condom on. I had brought some, so put it on and he sat on me, impaling himself with absolutely no pomp or circumstance. And he drove himself on me hard for nearly a half hour, fully enjoying the sensation between the pair of us. And I was not complaining, he was very good, athletic and into the experience. We’d been at it for an hour, many times he’d pulled himself off and dropped back on me, a couple of times we’d renewed the lubricant to keep the speed up, and all at once the sensations changed. I felt skin on skin. I really loved it, but had a sudden rush of panic like the condom had slipped off in him and this was going to be an issue. From the change of intensity and the overall pace, I suddenly realized he’d reverse stealthed me and taken the condom off mid-action. I felt honoured and terrified all at once. And it did not stop the intensity or the action.
Suddenly he began to pant and stopped on top of me, getting up off the chair and standing bent over at the bedside. I got up and felt compelled to grab his ass and immediately start to eat him, full force and vigour, even harder than earlier. He gasped and said out loud “oh my god – no one has ever done it like that before.” I did not care at all what he was saying, I was enjoying myself. After a round of this, he laid on his back on his bed and asked me to get back to it. I slicked myself up with lubricant and jammed back into him hard and fast, and began to really fuck him. He told me to take it easy, he needed to adjust to my size. I slowed down and started longer, harder, singular deep strokes we both were enjoying. And my speed picked up, and we started to have a far faster experience, going at it this way for a good long time, and he literally pulled himself a bit forward and flipped over and told me to just ram him. I grabbed his ass and began to eat him yet again. Harder and more thoroughly than the first times. My tongue probed him inside and I pushed it in hard, tongue fucking him hard and loving it all. Him as well, that was very clear.
More lubricant and back into him, hard and fast. We were both enjoying it and we’d been doing this 4 hours. I’d been holding myself and not cumming, so when he told me he was really sore and we’d have to finish this another time, I was both happy I had not spoiled the fun and unhappy I had not gotten off.
He didn’t EXACTLY apologize, but it was clear tonight was over. 2 times with no relief. I told him how much I had clearly enjoyed myself and got dressed, the peach thong still on me, dirty and matted with lubricant. At no point had there been anything distasteful, he had cleaned himself well before I arrived and the experience of going back and forth with him had not for a second seemed dirty.
And I began to think of a next time, if it came.
The third time
And then came Good Friday. Out of the blue, he messaged me. “Hey handsome, you free tonight?” Oh yes, I thought, I am free. It was 7:30 pm and he told me to come over as soon as I wanted to. I got it together after a shave and shower and headed over for the evening, arriving at 8:30.
I got to his place, went into his bedroom and disrobed. He told me he’d love me to wear some lingerie like last time. I giggled and told him I had cleaned my “uniform” and I had it on. He was suitably impressed. The room had that scent of vanilla I was associating with him. He was fully attired in lingerie, however he was clearly masculine in it. I know I was with a man, not a guy posing to be a woman. It was more a definition of roles and we both clearly enjoyed it.
I told him to get on his knees and suck my cock. He heartily agreed and got down to it right away. Slow and circling me, taking me in and down, I felt myself grow and started to get greedy and slamming it into his throat. I had to hold off from immediately shooting, he was clearly trying to get me to cum this time around. I laid back on the bed and he got on me, making guttural laughing sounds and enjoying himself. He did this for a while and pulled his head up and said he needed a drink of water.
He stood up, went to the dresser and had a sip on his drink. He invited me to smoke a joint. I’d brought some I grew the previous year of a dynamite strain I loved, so had half of one I rolled in front of him. I offered some to him and he took it and said “what – no filter? What kind of savage are you?” “I thought you knew that by now and that’s why you invited me back” I quipped. He began to tell me things about himself, that he fronted a band as a guitarist and a singer. I truly attract that type. I listened to him, he then out of the blue asked me if I wanted a “cock pill.” I said sure. He handed me a pill and I took it. Not clear on what it was, but figuring what the fuck.
He stopped sipping on his drink and started to massage his own ass. I knew it was time to play. I took out a bottle of cherry flavoured lube this time, not Astroglide, knowing how last time went and thinking this might be similar. I grabbed his vanilla smelling ass and jammed my mouth on it, viciously licking and sucking it from the very outset, which made him lose his breath immediately. I did not let up for the entire time I did this, having to roll his cheeks out of the way of my nose so I could simply breathe. He was scintillating and delicious, clean and I could feel his body opening up to my tongue, ready for something bigger than that.
He bent over the bed, I added lubricant and slowly opened him up – not fast, not impatiently, just a full experience of entering him and truly feeling myself come to rest fully inserted and hearing him catch his breath in the process. I pulled out and ate him again, and he threw me on the bed and sucked on my cock for a time as well, truly enjoying the exchange. I kept going back and forth and fucking him for bursts and eating him, and he was clearly loving it.
We kept at this, and it was coming up on 5 and a half hours together this time. I put him on his back on the bed and got on top of him, loads of lube on him and entered him completely. I slowly started to build in intensity and then picked up the pace, jack hammering him, with his legs up on my shoulders and looking him in the eyes as I jammed him harder and harder, him gasping and enjoying being so completely taken and me enjoying myself.
All at once this intense rush of flame reached over me and seared my lungs, I was dripping wet all over him and I felt myself truly let go. I had a feeling I had not had literally for years and I jetted in him, and I started to let out moans and screams, guttural and noisy, at the top of my lungs for truly 2 minutes. I collapsed on top of him, his legs went down on the bed and I felt his ass grip my cock and squeeze it lovingly, clearly a form of aftercare I had not yet experienced. Clearly there would be a noise complaint, anything for 7 blocks would now be awake with that experience.
At that exact moment in time, I was completely spent. Kim rolled me on my back and touched me all over and smiled, leaving the room to go clean up. I was unable to make sense of direction of a good 10 minutes while he was out of the room fully dehydrated and unable to reach the water some 5 feet away.
I slowly regained by sense of reality and Kim came back in the room. He said “I almost called 911 – I thought you were having a stroke.” I feebly broke out laughing and said “no, now you‘ll know for sure when I cum.”
I cleaned up in the bathroom groggily and came back to get dressed. It was clear between both of us 6 hours of action was enough and we’d both got a real thrill out of it. He told me no one really tops him and he was so taken with me he wanted that from me and really was happy I did that, and would expect that from me all the time. No one had ever done anything like that to him ever before. I felt very satisfied and thanked him with a hug and got in my car.
When I was nearly home, I texted him “THAT. was wicked. AWESOME.” He texted back “I agree hun. I can feel you humming all the way over here right now.”
Since that time, we’ve got together multiple times and he’s introduced me to a pantheon of playmates, male and female, with me being a top and fucking him with all the other players involved. He’s good trouble.
Source: reddit.com/r/gonewildstories/comments/n74s9c/third_times_the_charm_from_mmf_couple_to_mm