My First Anal Virginity

Once upon a time.....

My ex wife and i were swingers. We didn't call it that, but looking back, there's no denying it. We would frequently use the phone flirt lines that were so popular in the early nineties. They were normally free for women, so we would get the number she would leave the greeting message, and then we would suck and fondle each other as we spoke with guy after guy after guy, and occasionally a girl.

You see.... even though i was still in denial about being a sissy, she kinda knew it... perhaps it was the way i liked her to peg me with candles, or the ass-play that i didn't mind... idk. *giggles* She was quite the little repressed bi-sexual herself as well. While i'll prolly never know the truth (she was a g'damned dirty liar - but that's another rant for another day) when i met her, she had had a couple of mild lesbian experiences, but loads of fantasies - fantasies that i actively cultivated as we screwed each other like 20 year old rabbits tend to do. She was also fascinated with watching two men, as many girls are i guess, and she saw her chances to fulfill both our fantasies.

The phone lines were a good way to meet like minded individuals and arrange for casual meetings... the 'Craigslist' of its day. To my dismay (not really i guess, cause i went along...) the lines were dominated by guys (surprise!) but we found, many times, the guys had / knew of girls , or were just fronting for the ladies... and couples were always looking for other couples.

i guess, at that - at that time - i was prolly closer to hetero with bi leanings (for comparison, i would say today, i am gay with bi leanings, hehehe). So, i didn't mind the guys. i tended to be slicker with the ladies too, understanding them better. Many times, i was tasked with keeping the other guy to keep calm and relax, let the ladies get acquainted, wait for the right time. More than one idiot ruined the whole thing by being too eager. But once the action started, it would be girl on girl, boy on girl, swap partners, etc. Sometimes a guy would be adventurous and reach for my dick. Sometimes i would 'help' my wife by guiding his cock inside. If there was enough alcohol... eventually i'd be licking and tasting... sucking his dick... satisfying urges deep within that i still couldn't admit to myself, much less anyone else... but at that moment... i didn't care.. i would find myself lost in lust.....

~wheww~ excuse me.... *giggles and blushes*

So..... fast forward a bit. We were good at the game. We now had numerous regulars. A constant stream of girls wanting my wife, a few who would fuck me as well (wife loved watching me fuck... actively encouraged it and thoroughly enjoyed it). There were at least twice as many regular guys though, a a couple of couples. This whole deal went on for, idk, 3-4 years? All of the guys were at least somewhat bi, to varying degrees. That was key for her. One time we met a friend of a friend... who actively admitted he preferred guys, but didn't mind playing with girls too. And he brought a video camera.

This guy kinda intimidated me.. even though i was a bit heavier, hairier, and overall more manly than he. His openness about loving dick, his constant efforts to get me instead of my wife, idk why it scared me, but it did. Drink drink drink. Camera comes out.. not without many promises of total privacy... but it also was a turn on to think that he would play the video for our mutual fuck friends too. Smoke, Drink, Smoke, Drink...

Thankkies Jack :) You're a great friend!

So there i am. Missionary on top of my wife. Fucking away on the living room floor. The camera is on, recording every thrust and grind. Its a slow fuck, her legs around my hips, as i grind into her mons, kiss her face roughly, not moving very much. you see... guys tongue was working us over at the same time. I would feel him bury into my asshole, lick around my balls, then id see her smile and wiggle, he must have been giving her the same.... i remember her spreading my cheeks as he started on my hole exclusively.... fucker ate my ass for like 45 mins straight.... at least it seemed like that. It felt good, but strange. I was hung up on the fact that a guy was worshiping my ass. idk... i was young.... i didn't wanna stop... but at the same time... i wished he was a girl too....idk.

It wasn't until we stopped fucking, when i kneeled up, she kinda led me over to the sofa, pushing my shoulders onto the cushion, as he approached from behind that i realized.... he had been lubing me up!

i was mortified. i started to protest. He was calming and soothing, promising to go slow, to not hurt me, just try it, see if you like it. She was on my other side, stroking me, telling me how much she wanted to see it.. how hot it would make her, to do it for her, stop being a pussy..... and be a pussy.

Trembling, i went down. On my knees, face in the seat cushion, i expected the worst. Probably because of that, he had a bit of a difficult time getting in. It did hurt a little.... but not much. i know i exaggerated the fact, mainly to save my pride, but also to get him to back off before it hurt more. Before i knew it.... i was being rightly fucked.

Ummmm... not sure about this......

NNNNNN!!!!! More Lube!

Oh fuck... i.. uuuuhhhhhh... i.....never... knew.... oh yeshhhhhh!!!!

A man was inside my asshole, using it to get off in. He took my virginity, and was masturbating his load out with my virgin ass. omg. omg. omg. i heard myself moan like a sissy, embarrassing me further. Wife was right next to me, oooohing and ahhhing. She would stroke my dick a bit, but not enough. Stroking... in and out of my ass. Eventually, she got down and under me to suckle my limp dick. idk if she wanted a closer look at my subjugation, or if she was legitimately trying to please me, but at the time, my head wasn't accepting. i didn't know what i had, i didn't know what i was getting. God how i wish i could have that moment back....

Looking back... it was all about her desires....

Thats right you bitch! At least make me feel good too!

OMG...she's sucking me! I'm being fucked!

OMG! She's watchin me get breed! omg, my dickie is so small... i wish he would just cum and be done now!

And then..... he came. He came inside my cunt like a dirty rag. He didn't ask. He didn't use a condom (although... all of our playtime was condom free). He just used my hole. *BLUSH* it was sooooo embarrassing. He pulled out, she wanted to examine me... but i was having none of it. Running to the head, with my fingers over my hole... i sat and let his semen dribble from me. I was sooo humiliated. Of course, i didn't come out until i knew he was gone.

OMG i think he came in me!

A fucking MAN CAME INSIDE ME!

Get it out! Get it out!

Wot does this mean? Am i a faggot now? Am i truly gay forever? A: Yes.

Today.... i would have wiped then sucked out his last dribbles, and eaten his faggot fuck hole as i wanked all over myself in thankfulness for his attentions. The difference age makes...

That was my first time. i haven't been properly fucked in many years since....many years. While my dildo has loosened me... i feel like a virgin again in my mind? Do you think that's okay to say? Can i call myself a virgin again nows?