The sluttiest thing you ever did??..

One night on my way home from working out of town, I met up with a guy from Grindr on a road between a neighborhood and the interstate. We greeted each other and he rubbed my crotch through my shorts. I stripped off my shorts and shirt (I like to be naked) as he started sucking me. After a few minutes of him sucking me, I pulled him up so I wouldn't cum and lose my urge (I really wanted to suck a cock that night).

I recently decided that I wanted to embrace my bisexual side and experience as much as I can with another man. I began sucking him. I used one hand to play with his balls as I sucked him. I took every inch of his six inches and played with the tip too. After a couple minutes, he said that he was going to cum if I kept sucking. Before I started, I hadn't thought about whether I would suck him to completion, let him cum in my mouth or if I would swallow. When I heard him say that he was going to cum if I kept sucking, I didn't have to even think about it. I kept sucking as I felt him tense up and he came. I kept sucking as his cum pulsed into my mouth and I sucked out every drop. Unfortunately, I didn't swallow (It was my first time really attempting to suck dick, let alone letting him cum in my mouth). I stood up as he knelt down and began sucking me again. It only took a couple minutes and I was ready to explode. I let him know that I was about to cum and he pulled my cock out of his mouth and I shot 3 strong ropes of cum out. We cleaned up and went our separate ways. I drove home in pure excitement that 1) I sucked cock and 2) that I made him cum on with my first experience. I was disappointed that I didn't swallow. I made up for it when I got home because the first thing I did when I walked through the door, was to walk straight to my wife and give her a deep kiss.

My next bucket list item to check off is to fuck my wife after I've been fucked and filled with a huge load.

Sluttiest moment ever was blowing my best FWB and kissing his wife on my way out of the door with his cum on my breath and cheeks.

I made sure she got a taste.

I use to run a ad on CL and see how many guys I could get to stop over and I would suck them off ,some we'd do a 69 but mostly I'd put some porn in and set them on the couch and go to town til they came.
If I was working somewhere I'd have a stool or chair for them or I'd sit in the chair or on my knees and let them fuck my mouth til they came.
I like stuff like that

So Hot!

so as you all know back in the day I transitioned to shemale/tranny how ever you want to put it for 8.5 years.. I was involved in the trade during this time.. one of the craziest things I would get up to was my marathon days.. so once a week I would try and have sex with as many guys as I could fit in a 12 hour period.. basically 10am to midnight with a clean up break in the middle.. one particular day I was sent to 9 different addresses and met 10 different men was fucked by all 10 and took loads from all 10 and paid by all 10.. $4k that day.. there were lots of days with 6/8 men a few with 12/20 men in group play..but 10 was the biggest where it was one on one play..

I sucked a lot of cocks in one night at a hotel meetup and let a bunch of men take their turn blowing their loads on my face. I was covered and it was fucking hot.

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Originally Posted by Tight1-4u

so as you all know back in the day I transitioned to shemale/tranny how ever you want to put it for 8.5 years.. I was involved in the trade during this time.. one of the craziest things I would get up to was my marathon days.. so once a week I would try and have sex with as many guys as I could fit in a 12 hour period.. basically 10am to midnight with a clean up break in the middle.. one particular day I was sent to 9 different addresses and met 10 different men was fucked by all 10 and took loads from all 10 and paid by all 10.. $4k that day.. there were lots of days with 6/8 men a few with 12/20 men in group play..but 10 was the biggest where it was one on one play..

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just curious?. Did it hurt afterwards, taking in 10 cocks in a day?
Also was that safe sec (with men wearing condoms)?

Sluttiest F sex, fucked 3 different girls in a 12 hr period, one was my girlfriend, other two were friends of hers, to my knowledge no one ever found out. Sluttiest M sex, got fucked in a sling at a house party, 2 of the guys I knew, the other 3 guys were strangers.

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Originally Posted by dowmass

just curious?. Did it hurt afterwards, taking in 10 cocks in a day?
Also was that safe sec (with men wearing condoms)?

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no it did not hurt I was in the trade so I was getting fucked every day.. I have always had unprotected sex love the feel of skin on skin.. always wanted to feel his load deep inside of my pussy.. I also learned the trick of a very hot bath after either a lot of sex or quite aggressive sex where I could possibly Be sore after.. I get in a tub of very hot water and soak for a while letting me soak up the heat and relax slowly.. I soak till I am sweating profusely and am very very relaxed..I also douche between guys to stay clean except when in group play when I am taking load after load..

Before xmas i had my first visit to a sauna (bathhouse). In the coiple of hours i was there i sucked two guysand got sucked in turn. Felt like a real slut letting myself get groped bg strangers in the jacuzzi.
One guy asked me to fuck him bareback, which i was in no way going to do, neither had the first idea whether the other had hiv, syphilis or saturday night fever.
But for that it was fun walking round with everything on show. I had expected a lot less pubic hair to be on view. I was the only one shaved. Lookkng forward to my next visit.

Don?t know if this counts as being slutty, maybe just horny as hell. I was out at a local concert, with my wife. She drank a bit much and in the course of the evening was dancing and attracted the eye of a younger woman, who was all over her. I was so turned on and did all I could to get her to seduce my wife. I wanted it so badly. At the end of the night I tried to get her to come back to our hotel room and go crazy on my wife. She almost gave in?but her friends pulled her away, Upon being so turned on by this, I fucked my wife for hours that night, basically using her as a sex doll. She was so out of it, willing, but drunk, and I allowed every single urge to come out. In the morning, just the thought of almost having a woman have her way with my wife kept me so turned on. I literally mastubated on my wife for a few hours, cumming multiple times all over her. She woke up later and laughed asking? why do I feel so sticky?

I had once tried to get a younger friend of mine who I thought was so damn beautiful to fuck my wife. I wanted to have him just go crazy on her and wanted him so badly. It almost happened.

Two times I was a slut wanting something so badly.

When i was 17 i fucked 3 different teenage girls in one day!

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Originally Posted by Tj726guy

Before xmas i had my first visit to a sauna (bathhouse). In the coiple of hours i was there i sucked two guysand got sucked in turn. Felt like a real slut letting myself get groped bg strangers in the jacuzzi.
One guy asked me to fuck him bareback, which i was in no way going to do, neither had the first idea whether the other had hiv, syphilis or saturday night fever.
But for that it was fun walking round with everything on show. I had expected a lot less pubic hair to be on view. I was the only one shaved. Lookkng forward to my next visit.

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I should add that i was sucking and being sucked in feont of other guys, that made me even more hard

Quote:

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Originally Posted by Tj726guy

Before xmas i had my first visit to a sauna (bathhouse). In the coiple of hours i was there i sucked two guysand got sucked in turn. Felt like a real slut letting myself get groped bg strangers in the jacuzzi.
One guy asked me to fuck him bareback, which i was in no way going to do, neither had the first idea whether the other had hiv, syphilis or saturday night fever.
But for that it was fun walking round with everything on show. I had expected a lot less pubic hair to be on view. I was the only one shaved. Lookkng forward to my next visit.

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I go to Choi's spa in Saugus, Massachusetts quite regularly and have found that the majority of guys are either shaved or very well trimmed. I myself have no body hair and a very small patch of pubes trimmed so short they're barely visible.... Mmmm love smooth!

Wow! Hot!! You win the prize! Did your wife participate on day 2?

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Originally Posted by Tj726guy

I should add that i was sucking and being sucked in feont of other guys, that made me even more hard

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I sucked my first cock with an audience the other day. I really enjoyed being watched. I love sucking cock and want others to know it too. Even if I prefere feeding most of the time.

One guy started sucking on my feeders nipples. I took a break to do the same thing. It helped move him along. I fingered him a bit and got my reward. As usual with guys, no one said anything. I gave my feeder a quick low thank you and we all separated immediately.

I really would like a FWB that would talk about it

I finally got up the nerve to put on my bra and panties at the gym after a shower, and felt like a total slut walking across the changin room to take a piss in my pink satin undies.

I haven't had a lot of sleazy encounters with my guys unless you count my buddy and I occasionally spit-roasting a "third", but I've had a few with women in my younger years that might be so construed. Here are a few examples - let me know if any or all of them qualify.

In my 20s I had a few "three-woman" days, but one in particular stands out in my mind. I was at the time renting a small three-bedroom semi-detached house with my opera singer then girlfriend. For a couple of years we had neighbours we became quite close to, young couple, she (very French and incredibly busty) from Qu?b?c, he from Alberta. One time my girlfriend was away on tour for a couple of weeks and her husband was away on business at the same time. One morning there was a knock on the door and the neighbour lady was standing there in slightly diaphanous dressing gown, wanting to share a cup of coffee. She came in, I poured myself a cup and topped up hers and almost instantly we were madly making out. Yes, there had been some mild flirting and a bit of feeling of sexual tension between us, but wow... two minutes and we were in my bed, fucked each other's brains out for easily a couple of hours. Then she said she had to go back next door and check on her two young kids. Her younger sister had been visiting from Montr?al and had been looking after the kids while we were having our fun. I took a bath (no shower in that old house) and was surprised when a while later there was a knock at the door again.

This time it was the younger sister at the door. She was almost the complete opposite in appearance to her sister, being short and with tiny sweet breasts that were almost entirely nipple. I'd answered the door wearing only a bathrobe and she dropped to her knees, parted the front of the robe and took my cock in her mouth where she started to give it some serious attention - I think I was already hard before she got it in. I let her have her way for a few minutes and then told her that I desperately needed to be returning the favour so we went back up to that bed, I undressed her, sucked long on her luscious breasts and we 69'ed for ages and with many orgasms for her. We wanted to have intercourse, but she wasn't on the pill and I had no condoms in the house so we ended up doing anal, my first experience of it, but clearly not hers. After I'd finally blown my load in her ass (my 3rd? 4th? for the day so far as her sister had drawn several out of me earlier) she went home and I tidied up once again.

Mid-afternoon the phone rang and it was the younger sister of my best friend of the time asking if I felt like popping in for a visit. I guess at the time I was 22 and she was 19? Tall lass a couple of inches taller than me with long legs and small breasts she called her "cone tits". I arrived at the house thinking nothing more than we'd have a nice visit as we'd become extremely close friends at that point. She was home alone as her parents were out. Somehow it was not long before were started making out and one thing led to another and we had sex for the first time (her first time as well as it turned out). She was not only enthusiastic, but also a talented and imaginative lover. We never really "dated" per se, but we did have sex occasionally over the course of many years through various relationships and even marriages. Still a good friend, though we live several hundred miles apart and seldom see each other. Her parents were due to arrive home shortly so we sexy-showered together, I left and headed home.

It was a lovely summer day (about this day of year actually) and I'd planned on doing BBQ in the backyard. I got the grill lit and then the neighbour (both sisters and the two young kids) came over with some things to grill and asked if they could cook with me. Sure! We ended up sitting out back all evening drinking wine and chatting away. Finally it was time for the kids to go to bed so they went back inside. Around 11 PM there was a knock at the door once more and there was the older sister. We immediately took up where we'd left off and I think i finally sent her home about 3 AM. That was certainly a day to remember - and I certainly do! I think I counted 18 orgasms of my own over the course of as many hours and I must surely have provided at least twice as many. Ah, to still have that capacity!

Sleazy? It didn't feel like it at the time, but maybe in retrospect?

Another time - I was walking down the beach at the cottage around dusk one summer's evening when I chanced upon some girls I'd been talking with earlier in the day. They were sitting around a bonfire drinking beer. I got into a fairly intense discussion with one of the girls and then we decided we needed to go out "in search of more firewood". The only "wood" that ended up being "found" was mine and we had a good, long intense session in some shrubbery. Then we heard her parents calling her and so she went back and went into the cottage for the night. I was walking back along the beach to my family's cottage and encountered another bonfire at which was a friend's older sister. I'm 5'7" and she is what she calls 5' 12". Somehow we ended up making out and then had sex right there on the open beach in front of everyone at the end of which she had a very loud and flailing orgasm. For some reason we never really spoke of it again...

Last one - this was actually my very first time having intercourse at age 14 or perhaps 15. I'd gone to a basement party with a friend (lots of booze etc.), but knew absolutely no one else present. I got talking with this tiny, adorable girl named Carol, we started necking pretty intensely and the next thing I know she's undoing my belt. It was one of those big 60s style belts, it jingled when she was working on it and everyone started loudly singing 'Jingle Bells'. I started pulling her clothes off madly and stark naked we fucked like insane rabbits on the back of an old sofa in front of an appreciative audience. After the party I tried to track Carol down, but never without any success. Who knows, maybe I missed out on the love of my life somehow?

Ok, any of that sleazy enough for ya?

When I was 19 I was slim, had long legs, a slim waist & sported long blonde hair. I heard many times that from behind I kinda looked like a girl. So for a while I cross dressed & had several anonymous & semi anonymous encounters. I eventually plucked up the courage to speak out & got very verbal saying "Fuck me, fuck my pussy, cum inside me!" It was an incredible thrill.

I sucked a guys dick at a park wearing my wife's panties and swallowed when he came in my mouth

When I finally decided to give in to my urge to suck a cock, I met a guy through Craigslist. I went to his house and sucked him off. When I left, I texted another guy I had been trying to arrange a meeting with, and he was available. I drove straight to his house and sucked him off, too.

Last night…

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My buddies and i were riding around listening to music one night, when we ran across a red head I knew from a nearby town. Very sexy big breasted and beautiful ass. She got in the front seat next to me . After cruising awhile she leaned over and whispered in my ear that she would fuck all five of us! I said take your top off and show them her big playmate titties. Shej did as told. At a red light i looked back and asked are y'all up for it and saw the fear in the three in the back seat. Drove them to their car ,then me and best bud took her to a park , got her naked bent over truck and started fucking her. Felt great ,soon a car pulled up behind us and set there awhile watching me pound her sexy behind. They drove off and i shot my load in her ,then backed off and watched my buddy take his turn . We did it three more times in the next month. I had her a few times by myself. She told me a girlfriend of mine had shown her a picture of me at a school function, she liked what she saw and she came hunting for me. Great memory!

This was 3 years ago. A year prior I had finally lost my anal virginity. After watching a lot of pirn especially gay porn where the guy is in the middle fucking and getting fucked. I went to a bathhouse and went to the dark room was fucking and got fucked at the same time at lease 4 times in an hour. Still feeling horny after with my ass still cum filled I was walking around some guy stopped with an 12 inch cock. I was properly stretched so I took him for a good 45 minutes. Then went back to the dark room where I breeder 3 more asses as I got bred twice more.

I've done a lot of 'sexploring' in my adult life, but I don't think I've ever done anything that would qualify as slutty -- sexually adventurous, broad-minded, perhaps even kinky, but never slutty. There have, however, been a few occasions when I've done something that pushed the limits.

One one occasion, at my buddy Dave's request, I performed oral sex on him while he was engaged in a serious phone call with his estranged wife, Deanna. He was so turned on by this that a couple of weeks later, he called his Mrs. again, this time while I rode him in the cowboy position.