First Time 2026

Standard disclaimers of everybody being over 18 etc

Back when I was 25 or so and living in Santa Cruz I was involved with a woman who was a "late" bloomer in the sense that she gave me her virginity after she graduated college.

She was tall (5'9") small breasted with pink pearls for nipples.She could have been androgynous if she ever choose to emphasize that. Lets call her J

I was 6'2" about 240 lbs. Think blue collar construction.

A year later she is sharing a house, and a bed, with me and another woman. They used to joke about writing newspaper advice columnist's to ask proper convention as to choose which of the others to go to bed with at night. As she said once. it was a busy year.

I always felt some sort of guilt to her for taking her virginity, teaching her to suck my cock, and her learning to eat pussy in my presence.

One evening when she was apt. sitting for a friend whose neighbor was a gay/bi man of same age group, who was not "flaming" just another guy who was out, neater and better attired then I this was the early 70's. I enjoyed his company as he was part of a greater circle of friends. He was androgynous before that term was widely used or acknowledged.

So one evening the three of us were sitting around with some good pakalolo and wine. The conversation continued to bump up. Somehow the subject of the sensitivity of mens nipples came up. I admired that I had sensitive nipples and enjoyed women sucking on them during foreplay. The gay man expressed a certain skepticism and my lady decided to show him by running her hand under my shirt and over my nipples while kissing me. Next thing I am aware of is my shirt is open and they are both sucking on my nipples. Needless to say i was expressing pleasure with some slow moans and pressing their heads against my chest. At this point the gates opened and clothing vanished.

At the time I thought that surrendering my oral and anal virginity to cock with her participation would help balance the sexual/ karmic balance. Plus it was feeling real good.

First with J's encouragement I slid down and started too going into 69 with the man and I sucked my first and only cock as J mounted his face in reverse cowgirl. I remember looking up and see a look of carnal voyeurism on her face that was almost scary.

Then I pivoted to 69 with him using his cock in my mouth as the pivot point.. Shortly she joined me in bathing his cock with our tongues and mouths. she kept going back and forth between our two mouths and two cocks sucking eagerly.

She made a point of repeating what I had told her when I taught her to suck my cock, in my ear. Pay attention to the head, careful with teeth, keep tongue moving, don't forget the balls and finally just use your mouth not your hands.

Not to mention she kept repeating an adage I had told her that it seems I was a natural cocksucker and was more attractive with a cock in my mouth.

She was a good woman who I deeply cared about but she did have a streak of malicious humor.

He was generating a fair amount of pre-cum that she paid a point of ensuring that I licked with my whole tongue and swallowed, since I taught her that. When a large drop appeared on the end of his cock she made a point to back off and lightly push my mouth down on it.

Soon he said he was at risk of erupting under our oral treatment. This was true even as be played, and penetrated my anus with his fingers as he sucked me in 69. He was subtly signaling that he wanted to fuck my ass.

My girlfriend was equally subtly signaling she would like to see that. I felt that since I had taken her maidenhead (actually it was gone from physical activities - but God she was tight) that it would only be fair for her to watch/ participate in me losing my last cherry. So with me on my elbows and knees him behind me on his knees holding my cheeks open and her under my torso she reached backhand helped line his penis up with my anus held me to her breast and ensured that I kept my eyes open and looking at her as I was penetrated.After it cleared the tight ring there was not so much pain I winced and I took it like a man while staring into her eyes while seeking comfort in her bosom and sucking her nipples as he fucked my ass, She kept asking how it felt. I could not answer i would answer with my mouth and tongue an her nipples and eventually in her pussy.

Slowly I slid down her body, or she slid up, and started eating her pussy as he sawed in and out of my previously virgin hole. I looked up and saw her looking over me at him while he was fucking my ass as her legs came up and wrapped around my head pushing me further into her vagina. Some time later with interment moans from the from us all and before I could decide on whether I enjoyed this activity he thrust hard while pulling my hips back against his groin and filled my ass with his cum. I admit I was pushing back and and lower back were wiggling on his cock in my ass Then with a few strokes of her hand I too came and she rubbed her handful of my cum to my mouth and face.

Another first and only. I found out that among her girlfriends, number of which I had slept with, that she was not discrete but her version bordered on bragging, emphasizing her role in losing my gay cherry's by getting my ass fucked and blowing a man, she did say she pushed my face down on the cock, fair enough.

Afterwards when I thought about it and looked at other men, or had them make a pass at me, I when I asked her if she enjoyed herself she told me watching me be used by another man would feature in her future mastrubatory activities. During extended dry periods I often thought of it to break up my involuntary chastity. I never repeated it because I just do not find men to be sexually appealing. Even when I was going insane from frustration. In fact I do not understand why women do but thank Eros that they do.

And in retrospect thank god for intoxicants that lowered my inhibitions.

I hope she remembers that moment fondly.