[MMF] My ass is no longer a virgin.

*I’ve posted quite a bit on the Chastity subreddit and just the other day I came across this sub and I figured my story was worth sharing here.*

I’m a male who’s kept in chastity 24/7. If you’re not familiar with the practice this goes a long way towards explaining it:

*(edited slightly from Wikipedia) Chastity belts may be used as part of a practice of orgasm control, to prevent the wearer from engaging principally in sexual intercourse without the permission of the dominant, who acts as “keyholder”. A chastity belt will also prevent other sexual activity such as masturbation and oral sex involving the wearer’s genitals.*

*The putting on of a chastity belt, by a partner, is an indication of the dominance by the “keyholder” over the wearer’s sexual activities. By accepting the chastity belt the wearer accepts surrender of control over their sexual behavior to a partner, who may grant permission to the wearer to engage in sexual activity by removing the belt. The dominant may decide when, where, how, how often, and even if, the submissive is allowed sexual release.*

In the first half of last year when asked about my fantasies, I confessed to my SO and keyholder that I might be up for servicing men. Shortly after that an opportunity presented itself with a friend who is gay. My keyholder instigated things and it took on a life of it’s own.

Nothing more than oral service has happened because I’m always locked and my FWB, Paul (who’s name has been changed for obvious reasons) isn’t allowed to play with my ass. My keyholder is always present to supervise, but not to participate. In late November she informed me that she had set a date between the holidays and her gift to Paul was that he could top me. The Friday before and after Christmas Paul was invited over, not to top me, but because my keyholder wanted to see me rim him. Just like when I started sucking Paul, the first time rimming him wasn’t great, the second time was wonderful.

On the second Friday after Paul left my keyholder told me that his gift was that he could have me any way he desired, as many times as he wanted between whenever he came over on NYE and noon on New Years. My cock would be locked the whole time, but if I could orgasm from penetration then I should enjoy myself.

Sunday morning was time for prep— a little concerned that I was too horny to be left unrestrained my keyholder tied my hands behind my back before she removed my cage to shave my perineum, balls and the shaft of my cock. She trimmed up my landing strip and instead of stopping with just the beard trimmer like she usually does (to prevent in-grown hair) she broke out the razor—“I want everything on you baby bottom smooth.” Then she caged me, untied me, and flipped me over and shaved my asshole and ass. Then, against my feeble protest she shaved my armpits. Strange.

Paul came over early just before 5:00. I was wearing a pair of lace panties and a T-shirt and Paul greeted me pretty aggressively by grabbing my ass, flipping my shirt up and pushing his hand down the back of my panties. I felt a finger slide between my cheeks and find my asshole.

“You don’t have him plugged? Well, let’s fix that.”

We walked into the bedroom and I slid off my panties. Paul grabbed the lube off of the night stand and squirted some on to his left hand. Once behind me, his right hand guided me down in a bent position at the waist, hands on the top of the bed. I expected a finger but the next thing I felt was a quick brush of stubble on my ass and a tongue lapping at my hole. My keyholder walked in with a plug.

“You boys don’t waste any time do you?”

After a quick, teasing lick Paul pushed a bunch of lube into me. One finger. Then two. Then three. Then the plug. I slid the panties back over my hips and my caged, dripping cock and took a step to head out of the bedroom.

“So, I think it’s going to be better—I mean I’ll last longer if you blow me first.”

I didn’t need a second invitation. It had been nearly a month since I had tasted Paul—the two times I rimed him he came outside of my mouth. I got on my knees and serviced his cock until his tasty load was sliding down my throat.

We had drinks for about 45 minutes and then Paul, just a few sips into his second martini looked at me and said, “You ready to get fucked?” I reached over and grabbed his hand and led him into the bedroom, my keyholder just a step behind us. Paul stopped me at the end of the bed and turned me around to face him. He looked into my eyes as he hooked his fingers in the waistband of my panties and slipped them down. He then dropped to his knees in front of me and sucked on my balls while he wrapped a hand around behind and started wiggling the plug inside me. Fuuuck, I was hard. After a few minutes he pulled the plug out and stood up. He commanded me to get on the bed and lie on my back with a pillow under my hips.

I started to freak a little—I always imagined that he would fuck me from behind, doggy, and when he spread my legs and crawled up between them to fuck me missionary, my dick turtled in record fashion. It was a strange shift—one that’s probably hard to wrap your head around unless you’re experienced it yourself—suddenly instead of having a dick in my ass I was going to have sex with a man. Somehow watching Paul take time to leisurely lube himself up, hand lightly stroking his cock, taking great care to spread the lube evenly—all with a wry smile on his face, snapped me out of my anxiety. And when Paul deftly pulled back his foreskin, wiped lube on his glans and then rolled his foreskin back over I was so ready to be fucked.

Paul entered me fairly easily only coaxing a small grunt from between my lips and asked with a smirk, “You sure you’re a virgin?” I didn’t bother to answer him because I knew the look on my face told the whole story. A real cock—warm, swelling and contracting, attached to a body that instinctively knew how to thrust, was amazing. I tilted my head back and let myself moan. I looked over at my keyholder sitting where she does when she watches us and she wasn’t just rubbing her crotch through her clothes but she had her jeans opened up and her hand shoved down the front, moving side to side in a quick fashion.

I’ve never been able to come from pegging or toying my ass. I’ve got a small prostate and my keyholder really doesn’t take my ass often enough to be good enough with the wand no matter the size. And even though I was experiencing wonderful sensations with Paul, after about 10 minutes I was starting to have serious doubts about being able to come. Then Paul flipped me over and instructed me to “stay on all fours no matter what”. He mounted me from behind and immediately my prostate was in the game. After a few minutes he shifted from behind me to above me and my prostate was getting punched with every thrust—AND I CAME. Fuuuuck! It was beautiful! All kinds of noises were coming from me and when I stopped Paul stopped and lowered himself down so he was behind me again. “Don’t move.”

Whenever I’ve come with something in my ass I feel like I want to take it out right then—but this was different. Paul wasn’t finished with my ass yet—he still needed to use it to get off. And realizing that pressed my submissive buttons in so many ways. After about a minute pause Paul started moving and he hammered my asshole, occasionally reaching out to feel my smooth armpits (I guess it’s a thing with him) until he collapsed over my back in orgasm.

After a few minutes on top of me, Paul pushed himself up, slowly pulled out, slapped my ass and walked into the bathroom. He showered and then cooked dinner while my keyholder reclaimed me by unlocking my cock and fucking me cowgirl until I orgasmed—my first with her since May 28th. Just to put a fine point on things, before she climbed off she scooped a wad of cum out of her pussy and fed it to me. My cock was locked back up before I even stepped into the shower.

My night wasn’t over though. After we wrapped up a long leisurely dinner Paul went out downtown to meet a few friends. We heard him come in the front door shortly after 1 am. Minutes later my phone chimed. It was Paul making a booty call. I looked over at my keyholder and said, “He wants me.” “You better go then.”

Paul was lying on his back on the bed with his hands tucked behind his head. The only thing he was wearing was his signature smirk. He had me suck his cock for a few minutes before I was instructed to lube him up and mount his cock, cowboy. “Take it slow. You’re not used to riding. Don’t break my dick.”

I rode him for a long time—long enough to work up a good sweat and when he got horny enough Paul couldn’t help himself. He told me to get off, flipped me over and shoved his cock into my ass. Things were different without my keyholder present. Paul wasn’t forceful but things were more intense. This was about him using me, not giving me an orgasm. He came within minutes. I stopped off in the guest bath to wipe my ass before I went back to bed but as soon as I hit the mattress I could feel the cum running out. “Did you come?” “Not this time.” “Good.” It was the first time my keyholder didn’t reclaim me.

The next morning Paul wanted to fuck in the shower. We have a big walk-in shower but everything is hard surfaced so we started standing up. Eventually we ended up on the floor with Paul above me punching my prostate. I didn’t come and Paul had a hard time himself. We stopped completely twice, but each time I found myself soaping up his drooping cock and bringing him back to life. I got him pretty wound up—to the point where he was goal oriented—it reminded me of the days when I would (and could) jack off 3 or 4 times in a day and the last time was often more about finishing what I started than it was a desire, much less a need to come. Finally after at least a half hour of fucking he came with a long moan in my sore, well-used ass.

Before he pulled out he slapped me on each cheek. “Happy fucking New Year.”

Source: reddit.com/r/gonewildstories/comments/7pgwyq/mmf_my_ass_is_no_longer_a_virgin