I am a 42 year old, gay, transexual, man from a major city. For a while my life centered around pleasure based sex ed & I also taught kink classes. My service submissive is a 30 year old slutty trans faggot, darling bitch I met on an app when I posted an ad titled “Are you a good boy?” We chatted for a bit before meeting & I was overjoyed to learn that he’s particularly focused on service, protocol, chastity & giving head, as I love training for best service, including getting perfect head. Over a year later & things are better & hotter every day.
Things to know about us: we are both transexual gay men who are into the leather lifestyle. We have each had top surgery & still have our original bits down below, though enhanced by testosterone. We both happen to use the words “dick” &”hole” (hope you follow) to refer to our junk, & we both happen to be multi orgasmic; me much more than him, but as we mainly do chastity/denial/ruining with him, I don’t actually know how many times he can cum. Before this weekend, we’d topped him off around ten. I have given up divulging anything near the exact number of times I cum because most guys don’t believe me, as the average for someone with a penis is one. I now say “dozens & dozens” because that’s more digestible than saying “hundreds” or “After my first orgasm I will likely have continuous orgasms for the rest of the time we fuck.” The one thing about that is that I don’t typically feel done after orgasm, I just stop when I’m at a good stopping point.
Our weekend together started on Sunday. I told my sub to make me brunch when I got to his place. I didn’t get to see him all week, so we cuddled for a bit before I was ready to hear about his time at a gay sex party the night before. I’d been going to that party for years, & we went together last time. This was his first time going alone, though certainly not his first rodeo.
I’d told him that he could only wear a chest harness, boots & knee pads, so he was quite naked before anyone else was, which made him feel exposed in exactly the way I hoped. I have control over lots of things, particularly his orgasms & masturbation, & in preparation for no nut November, I’ve been telling him to cum as much as possible.
he got his front hole fucked while in a sling by some really hot dude with a dick way bigger than he’s used to taking, he came on it twice. he also swapped head with another dude we’ve played with before, & came a bunch of times while that dude sucked him off.
After we’d caught up for the week, & he’d drawn me a bath & given me a pedicure, I told him to suck my dick. It’s almost easy to forget that I’ve gotten, like, world class head by subs I’ve trained before. (Back in the days of Craigslist, I used to just ask for a mouth that needs a FTM dick & would get an expert cocksucker.) Thing is, somehow my bitch is even better. he was perfect the first time, with innate reactions to my body, & he absolutely loved getting trained to do it even better. I’d been so horny last week that I came over & over, way harder than usual. So hard, in fact, that I had to take a break because I felt faint. (I have high blood pressure.) After recouping, I asked if he felt like going again & he said “yes please.” Adorable. Again I came & came & came. I squirt occasionally, & when I shoot in his mouth, he is to say “thank you Sir” & those 3 muffled syllables always make me cum harder. I asked him if he wanted to get fucked & he said “yes please” so I grabbed a harnessed dick & fucked him. I top lots of ways, & a strap is never my go-to, but I was so horned up I needed to put his feet on my shoulders & plunge into him. In just a few strokes he asked to cum, I said yes, & the sight of him cumming & the extra pressure against my dick from his hole squeezing the piece inside him made me cum, which I don’t always do with a harnessed dick. We both came together a few more times until we were both spent. Sunday’s sex was hot, connected, & urgent. Fuckin amazing.
Halloween, being the last day before NNN, I wanted to get my sub to cum as much as possible, but I was also tired. I managed to freshen up his crew cut (I’m an amateur barber with a crew cut fetish, so ofc I have my sub in a crew cut) & after he’d showered, I gave him a magic wand & told him to masturbate. I held him & poured a low growl of filthy things into his ear as he whimpered & got off over & over. I don’t know how or why he is multi orgasmic, but I know that I wasn’t until my 20s, when I was submissive. My dom, at the time, would tell me to cum over & over, & since he said to do it, I made it happen. He’s a fuckin asshole, but he unlocked that capacity in me, as well as the understanding of how powerful Dominant suggestion can be. As my bitch got off, I said something I’d been saving for a while: “that’s not even your dick. That’s my dick. That’s my bitch dick & I want it to cum.” When I tell you he did, I mean like I’d never seen him cum before. Over & over louder & louder as I said things like “Give me what’s mine. That’s my cum,” until I suddenly told him to stop, stood up on the bed, & shoved my dick in his mouth. I fucked his face & shot down his throat until my knees were shaky. Then I laid back next to him & told him to give me more cum. Which he absolutely did.
We went on a little walk hoping to see some Halloween costumes. We’ve been in this dynamic for over a year & stepping outside after such amazing sex felt very much like new relationship energy. Our walk led us to the park where we first met in person. He was so extremely shy & awkward I had to remind myself that this was the same guy I’d been messaging. Now he was bubbling over with conversation. I had to stop him, I wasn’t listening. I’ve been in love with my sub for a while, but it felt like I fell through a trap door & found so much depth. I love him in my guts & I’m amazed that it just keeps getting better. I told him so right then.
Today was the last day of our weekend together, which meant I had to assign my sub’s jerking off for the next few days. I told him to buy a Satisfyer One Night Stand, which is a very cheap, non rechargeable suction toy that comes with about an hour’s worth of power before it is useless. I said besides hygiene, he is not to touch my bitch dick until the toy arrives, & when it does, he can only jerk off with that & use it as much as possible until it dies, hopefully mid-wank. Suction toys tend to be excellent for quick, powerful, orgasms & today being the start of No Nut November, he’ll soon be having some 1 minute roller-coaster sessions, rocketing toward orgasm only to suddenly have to stop.
We spent most of the day in bed just cuddling, but he did suck my dick again. Our usual is me laying back & us going back & forth between him bobbing on my dick & me fucking his face. At some point maybe 20 minutes in I said “show me what you can do” & his body language changed. He locked into cocksucker mode. I let him do all the work & tbh, he’s always literally amazing, but sometimes he’s purely sublime. Like, the ultimate capability my body has for pleasure, 100% max, for like at least an hour. I came so much I may have actually finished, (which isn’t really a thing for me) but then he kept going & I may have cum more? I growled. I laughed like a madman because it was so overwhelmingly beautiful. I’ve seen visions a few times in my life while feeling so much delirious pleasure, so I was excited to get to that today. The visions are always round, succulent, & full of life. I could feel this forever. Infinite, infinite. Until it wasn’t. Until I remembered I had to get going soon & he had plans. He was content, but I was a mess. I took a nap right after, but I’m still a mess & really not over such a wonderful weekend.
Source: reddit.com/r/gonewildstories/comments/yjxxjo/tm_4230_trans_man_ds_hot_fuckin_weekend