Jay went 26 years with his straight virginity intact. Ava helps Jay surrender to an urge he never acted on outside of the occasional straight porn video.

Jay Surrenders His Straight Virginity

Road To Vaginal Penetration

On our 5th three way, Jay decided he is ready to fuck me. We began by all fooling around as normal, I delight in viewing my men making out, we take turns sucking Jay and Vance. Vance fucks me while Jay watched and worked up the nerve to enter me.

Seeing how much enjoyment I have from Vance’s cock inside me, Jay is ready to go after Vance came. We pull out a condom, as I am only fluid bonded with Vance, and slide it onto Jay’s cock. Jay gets on top of me missionary style.

Jay Penetrates Ava

I reach down and help guide Jay’s virgin cock into me. Vance is watching and holding his breath as Jay enters me. There goes Jay’s gold star gay status, however we have no regrets. Jay kisses me, Vance watches wide eyed and moans. I can feel that Jay is nervous so I try to help him relax. I pull Jay closer, kissing again, and gently moan in the heat of the moment.

We continue for a few minutes, and Jay lets us know he wants to stop. Jay was unable to cum or keep his full erection, he was semi-hard for our first time together. I did not take that personally, I think the first time I’m with Lenore I’ll be thankful I don’t have an erection to maintain.

We paused for a few minutes, then continued with our pleasure having successfully taking Jay’s straight virginity. Ultimately we did all cum at least once that night. Jay and Vance pleasured me with a toy while lying on each side of me. I flailed in pleasure, moaning loudly as I came, but I didn’t ask them to stop the continued stimulation spurred my orgasm to continue into rapid multiples.

Following Sessions

Jay, Vance, and I have met up an additional two times, our 6th and 7th three ways. Each time Jay has fucked me, and each time he has cum inside me with the condom on. I think two out of three times cumming by penetrating me is wonderful for a gay man! The 7th time, Jay and I hit a very pleasurable rhythm, I began building to orgasm, but then plateaued. So while I didn’t cum during penetration, we both experienced a lot of pleasure.