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Taking the plunge...how did you do it?

funkeymonkeylove said:
I think this is the dilemma for too many of us looking to expand their horizons and needing sexual release. Many of us married men in a non sexual marriage looking elsewhere with so much on the line to loose if found out. So many trolls and not enough looking for a genuine hook up.
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I agree.
 
NCWSLvr said:
So my story is in my 20s I learned about gloryholes and eventually I need to know what it was like. The nice thing is you can leave anytime - even in the middle if you wanted. My first time was exciting and not great. My next time going was awesome, and so I would visit every few weeks, for years. I had the blessing of my girlfriend who thought it was hot. We broke up, but my next girlfriend (now wife) I had told her about it before we even started dating. Must have sucked a hundred cocks over the years. Sometimes its hot, sometimes its not. Eventually I just stopped going. Still fun, but Im doing other things now.
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Lucky to have such a wife!
 
Curiousforcock24 said:
Here are the details for those interested.

Gave my first blowjob to completion and loved it. He was very patient, I was so nervous but he didn't push. We talked about various things not sex related and also my long time desire to do this and how he came to realize he was bi. He started off giving me a foot rub, then we eventually stripped down and started of jacking each other. First cock i've touched other than my own, he is cut, i'm not so it was very different. Then he asked if I wanted to suck him, I hesitated a few seconds then got down between his legs and started lightly sucking his balls eventually licking up to the head. I licked and nibbled on the head then took the head in my mouth and started sucking it. He was not too big, 5.5 and thin, just right for me to start with. I took him all the way to the base over and over and he commented that I was very good. The practice had paid off. I asked if he came alot and he said yes. I always imagined myself swallowing but wasn't sure about it this first time. But I wanted the whole experience and when he came I kept sucking and swallowing. Honestly, it had little flavor and there wasn't as much as I expected. All in all it was great.
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Sounds very similar to my first time.I was very nervous but he had experience and was very patient
 
I’m married bi completely discreet. I first acted on my gay fantasies when I was 23. I had one experience in Adult Theater when I was 22 and that made me fantasize more but as I did I found I was drawn to being the sucker and the one being fucked. I met with guys online and one day just decided to go for it. First real guy I met I sucked for a while and he fucked me twice before I came jerking off as he fucked me. I was hooked. I’m still a discreet bi bottom, although I’m pretty sure if my marriage was to end I would become gay. Gay sex for me has been the most fulfilling sex ever, I still enjoy sex with women but really get off on taking cock more. Sex with guys for me is just hotter than with women, and as a modestly endowed bottom, I feel there is a lot less pressure. Even if I come fast or can’t get it up for a long time I can still enjoy sex physically and mentally with men more than with women.
 
When I decided to act on my desires to bottom for a trans woman, I actually chickened out the first time and didn't go through with it. The next time, I basically forced myself to go even though I was super nervous.

As soon as I felt her cock penetrating my hole, all my nerves and fears vanished completely. I was thrilled when she pumped her first load of cum up my ass and took my anal virginity.
 
I was coxed or groomed by a 50s coworker in my 20s. I slowly converted and trained me to his sissy faggot. It ended with having body totally shaved, makeup, wig clothes and heels. He hired an Asian nail salon lady to come to his place to shave me and make me over. This sessions were so hot as I built anticipation for my dom to use me.
 
I guess others knew long before I did because I had been hit on several times by men I knew, and strangers both. It set up a deep homophobia within me that should never have been. I had a gay friend that I defended a lot in school, but I had to say no every time he asked me to try it. It is scary to admit this here, even now in this type of forum, but it is a huge part of my story. The truth was I really just wanted him to take me, and introduce me to bisexualism without asking, but he never did. I understand why, but wish he had.

Decades later I moved to a new home where just down the road from me was an openly gay man. Driving by one day he saw our house was on fire and called the fire department who got there just in time. In thanking him for his awareness, nothing began that night, but a friendship was started.

A few visits later we were discussing life and some history and an offer was made. He was very patient with me as I gave my first-ever blowjob. I had given a few more after that, when one day, knowing what I admitted about my friend, he never asked and just urged me off my knees and onto his bed. Again, he was patient as he took me there. It was not forced, I could have said no, but in the end I am glad he did. It was just what I needed because had he asked I would have said no. I still feel guilty about it sometimes, but also really enjoy it.
 
Curiousforcock24 said:
I want to explore my fantasies of giving head and getting anal. I have had these desires for a very long time. However, I need to be very discrete due to my family and work. I also don't want just some random meet in public, I want to be comfortable and take my time without looking over my shoulder worried about being discovered. Any advice?
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Online meetups on Sniffies.com. You don't have to commit to anything. Meet some guys with similar interests.
 
First time for me was a slow ordeal. I mean, meeting the man under non-sexual circumstances, getting to know him, accepting his advances and enjoying a full-on homosexual relationship (all in secret, of course). Just take your time and get a feel for the man's personality. You want to feel safe and trust him to a large degree. Once that is established you can explore the depths of depravity if you choose - and know you're in good company
 
Swuchrow said:
I was coxed or groomed by a 50s coworker in my 20s. I slowly converted and trained me to his sissy faggot. It ended with having body totally shaved, makeup, wig clothes and heels. He hired an Asian nail salon lady to come to his place to shave me and make me over. This sessions were so hot as I built anticipation for my dom to use me.
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I can’t help but think how different my life would be if I had had a friend like yours. I hope he has photos of the little flower he created that night, both before and after.
 
AOL and being a horny, curious 21 year old made me brave enough to invite a chatroom stranger (not that strange, he turned out to be living 5 blocks away) to my house and just let myself do what I've been dying to try and turned out came naturally
 
saintcero said:
I can’t help but think how different my life would be if I had had a friend like yours. I hope he has photos of the little flower he created that night, both before and after.
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Many years ago and he has since passed. He did have pictures and videos of us that his son’s probably inherited as part of his estate.

He gave me a gift of being a sissy faggot which I needed to balance my daily alpha side.
 
Terrylipstick said:
I got my start in an old fashioned Adult Bookstore video booth, before the internet was a thing. I kept driving by the place and just stopped in one day. I checked out the magazines and vhs tapes. They also sold toys and lingerie (which I loved to wear). After a couple of visits I bought some tokens and went into the back, I found a booth and dropped them in. This place only had two videos available per booth, all booths were different. When I started seeing the gay porn, I ducked into another booth. That’s when I found the ‘shemale’ videos. It wasn’t too long (maybe one or two trips) that I saw my first cock come through one of the holes in the wall. I freaked out and bolted….. but I returned. The next time I went in, i knew what I was looking for and when a cock came through the hole I dropped to my knees and gave him what we both wanted. When I walked out, I felt like the guy at the counter knew that I’d sucked my first cock. He smiled at me every time I went back, several times a week, for years. I miss that place. It is definitely where I took my “plunge” into cock, that led to sooooo much more. Good luck to you :)
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My story is so much like yours. I had sucked cock when younger but it was in a small town in what I call a horny neighborhood. Thenmet girls, married and had a child. Sex at home slowed down and I h ad recently taken a job in a big city. I would drive by an ABS everyday and finally stopped and went in. Like you glory holes were unknown to me but I learned fast and began a long relationship with book stores and there probably nothing I haven't experienced there. I've met a few men that we that we took our relationship beyond the book store.
 
I crossdressed since my youth. I was divorced and early 30's, living alone. It was before the internet so buying clothes and toys, everything was much more difficult. But I had fallen deep into it with a nice wardrobe, staying smooth and exploring with my own set of dildos. A friend's father in-law had come out as gay later in life. One day while I was watching my friends house there was damage from a storm and his father in-law called me to meet him at the house. By chance while I was bending over my sweatshirt pulled up and my pink thong peaked out. I didn't realize it but when we went to sit down to talk about what to do next with the damage he mentioned what he saw. He was very forward, but he made me feel comfortable enough to share my, until then, solo interests. Over time we met and he encouraged me to explore my cross dressing to the point that most people probably thought I was a woman. He was ruggedly handsome and in great shape. One thing led to another. And it was about as natural as it could be for me to do all the things. I lived mostly at his house for a while, which was awkward for my friend. One night he insisted that I wear a sundress and high heel wedges, makeup, the whole thing for dinner with him, my friend and his daughter. By that time I had pierced my ears, my long hair was cut and styled like a woman, my nails were done at a salon. After they left we were sitting on the patio and he took me bent over the chaise lounge. I remember squealing and begging for his cock. That was a unique time in my life.
 
I experienced my first cock(s) by visiting a Denver bathhouse in 2019, and I've visited other bathhouses in Dallas and Atlanta since then.

My favorite, though, was when I stayed at a gay resort in Palm Springs. The only problem was that I ran out of time and could only stay one night. I'm trying to figure out how to arrange a return trip.
 
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