by John

Gender: Male
Age: 58
Race/ethnicity: Caucasian
Current location: Texas
Highest education received: College degree (eg., BA, BS)
Occupation: Retired
Relationship status: Married
Religious affiliation: RC
How religious are you? Very
Sexual orientation: Gay/Lesbian
How many sexual partners have you had in your life (including oral sex)? 1,000+
How many hookup stories have you here posted before? 0

First Anal Receptive Sex

How long ago did this hookup happen? Six months

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He is tall, and pretty heavy, having lost a lot of weight in prior year.  He’s in his mid-60’s, about seven or eight years older than me.  We met through a gay hook-up site.  We hooked up at his home.   He is part of a long-term gay relationship, and seemed like a nice guy from the emails we exchanged.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had exchanged some emails after connecting through a gay hookup site.  I got an email from him one morning asking if I could come over.  I just happened to be out and it was pretty easy to sneak away, so I rushed over to the city that he lives in, about a thirty minute drive, and met him at his house.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He met me at the door wearing only a towel.  As soon as I came in the door, we started making out, which felt really good.  Then we went to the bedroom, and he laid on his back on the bed naked.  I took my clothes off as quick as I could, and set my bottle of lube and condoms in my shoe so they would be handy.  I got naked and joined him in the bed, sucking his cock.  Very nice.  After a while, I asked him to fuck me.  He is a big guy,  with bad knees, so he asked me to get on top as he lay on the bed. He had lube beside his bed, and lubed up.  I thought about the condoms in my shoe, but was too hot to bother with them.  I thought that it would hurt going in as it was my first time, but he slid right into me.  I had been stretching my ass for several weeks before this, which often hurt, but it was smooth as silk when his cock slid into me, and it hit all the right nerve endings because it was incredibly pleasurable.  I felt like I was in heaven, like this was what I had been meant to be doing all my life, and felt some regret that I had wasted my life trying to be straight when this was like all the lights of the heavens opening up, and every fiber in my body exploding in pleasure and joy. I stayed on top like that for a long time fucking, and kissing. We fucked for a long while like that, then he fucked me doggy for a while until I came.  Then he got on his back again, and I sucked him for about another 45 minutes.  He was enjoying it, but couldn’t cum and I had to get back home before it got too late (before my wife wondered where I was).  So we showered together, got dressed, and promised to meet again.  He saw me to the door, and I gave him a passionate kiss before leaving.

Did you have an orgasm? Did your partner(s)? Yes, I had an orgasm while being fucked.  He didn’t cum.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No, no precautions.  I was tested six months later, and am negative.

What were your REASONS for having this hookup? I have been gay my whole life, but was in incredible denial until about five years ago when I finally figured out that the reason I kept sucking cocks was that I’m attracted to men.  I fought against it my whole life, and lost the fight on a regular basis.  My wife never had much interest in sex, and I always had to use gay fantasy to perform with her, usually vocally, until we finally just gave up on it and stopped having sex a couple years ago.  Once we stopped having sex, I felt free to do more than just blow jobs.  Those are risky enough, but I never wanted to do anything more because of the risk of passing something on.  But now I felt free to explore.  Wish I had figured this out a long time ago though, before marriage and kids.

Were alcohol or drugs involved? If so, how much? No, neither.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt great about it.  He was a nice guy to be with and the sex was wonderful.  I felt incredible happy and joyful for several days, kind of on cloud nine.  I felt a bit of a nostalgic regret that I had not acted on my same sex attraction as a teenager and come out of the closet 40 years ago, and in some ways felt I had wasted my life.  Everything came together, and I understood why I have had problems with depression throughout my life.  But I feel trapped and can’t come out, so there is a joy that I will never have.  We have been in touch periodically, and if I can get away again, I will have sex with him again, and maybe with his partner too.  I am a bit jealous that there are men in long-term relationships while I am married to a woman that I don’t have feelings for.

To whom did you talk about the hookup? How did they react? I spoke to a Catholic priest about it.  He told me to stop pretending to be someone I am not and to come out.  He said that I will never fully become the person God has meant me to be unless I fully accept who I am and stop living a lie.  He told me that I can’t have it both ways, and need to tell my wife.  I was very close to telling her, but it just seemed that it would hurt her too much, and so I have tried to live without any sex, accepting that I am gay but not having sex.  It isn’t really working, and I want to have sex with a man really bad.  I have had sex with another five guys since then, but would really like to be in a relationship.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and VERY much a wanted experience for both me and my partner.  OMG, it was the fulfillment of everything I wanted all my life.

Do you regret this hookup? If so, why? No regrets.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hookup was the feeling that this was what I was made for, that this is what a gay man is supposed to do, that my sexuality was a gift from God, the intense pleasure and joy.  The worst?  Regret that I have spent my entire life trying to will myself to be straight, and have created a prison for myself worse than any jail cell.  It has so solidly reaffirmed my understanding of my sexuality as a gay man, and made me grateful for both being gay and for finally understanding that important part of myself.  It did make me appreciate the human contact and experience very much, something that wasn’t present in the hundreds of oral sex encounters over the years, and that made me long for a male partner, a long term relationship, that I don’t suppose will ever be a part of my life.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? This was probably the first time I really had a connection with a human being during sex.  Heterosexual sex was always difficult, mechanical, and a performance.  Previous gay sex was hot and lustful, but never with emotions or such positive feelings.  This was the first time that I had ever been fucked in my ass, and I felt so bonded with him and a lot of regret that it was just that, and I had to go back to my false life.

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