First Time With Dad's Friend

I have known I am bisexual since I was a teenager. I have masturbated to the idea of men, to gay porn, I've crossdressed at different stages, but I had never done anything about it.

Sure, I'd toyed with the idea. I flirted with a friend for a while, I have chatted with men online, I've had phone and cam sex with dozens of men. But I could never work up the courage to do the final thing.

On New Year's Eve, I told myself that would be my resolution. I love my wife and I love women, but I need to do this.

Last weekend, I got my chance. One of the men who I first realised I was attracted to was my dad's friend V. He is early 60s, divorced tall, tanned and muscular and he is largely the prototype for what I like in a guy. I have wanted for so long to touch him, to suck him. I've had chances to throw myself at him but always bottled it.

But last weekend, there was a chance to be bold and I finally took it. My aunt was turning 70 and having a party. When my wife and I arrived, I realised he was there. Given my resolution and the timing, I thought it was a sign and got excited and scared.

When I said hello, I made sure to give him a hug that lingered, with my hands low on his back. I then managed to manoeuvre into a conversation with him and my uncle, waiting til my uncle went to the toilet to lightly flirt and joke with V. I figured it was good cover. If he said anything, I could play it off as joking, but he didn't. He seemed to reciprocate, so I kept it going and as the night went on it got my brazen. Jokes about him sleeping alone, jokes about me being good with my mouth, touching, his hand on my leg under the table. At one point he looked at my wife and told me I was a lucky man. When I joked I'd ask her could he come home with us, he told me he wouldn't want to share, to which I replied "share me or her?"

Near the end of the night, he went to the bathroom and I waited and followed. It was just us at the urinals as someone left. I looked at his hardening cock in his hand and reached over and began stroking it.

"You wouldn't have to share me." I said.

A noise at the door made us stop and when I went out my wife was ready to leave. As I was saying my goodbyes, he quietly asked me, nearly begging, to go to his house on the Monday after.

Sunday was torture and I didn't get much sleep, but on Monday as my wife went to work and I told her I was working from home, I was bouncing with excitement. I showered and shaved more closely than I had in years and drove the 20 minutes to his house. Outside, I thought I could leave without anything else but the pull was too strong. I nervously walked to the door and pressed the bell.

He answered in a bathrobe and I couldn't wait to see what was underneath. He led me by the hand up the stairs to his bedroom, where he told me to get naked, which I did, already rock hard. He directed me to lie on the bed and then took off his robe, revealing a really lovely body from years of gym work and climbed on top of me, kissing me. I wasn't sure he'd want to, but was glad he did. He was passionate and his rough skin felt different but incredible. I had my hands all over him but could not resist going for his cock.

It was frenzied but it was our first time and we kissed and stroked each other for some time before he asked if I wanted to suck his dick. I let the cat out of the bag at this point and told him I'd wanted it for 20 years. This seemed to turn him on and as I was beginning to lick and kiss his cock, he urged me to "show him how much I wanted it" which flicked a switch in me. I went at his cock like a madman, sucking and licking and eventually letting him fuck my mouth until he eventually flooded my throat, causing me to cough most of it out onto the sheets.

I've been thinking about it ever since. We're meeting again on Monday.

Comments

Anonymous

by Anonymous on Jan 24, 2025 at 5:01 PM

Your first time is never your last.

(2)  (0)
Anonymous

by Anonymous on Jan 24, 2025 at 6:46 PM

I've been gay and kinda sissy since like forever. One of my parents good friend's Jason has always been really nice to me and not looking at me like I was a freak because I date boy's. When I got into my teens I asked my mom why Jason isn't married and knowing my sensitivity she was reluctant to say anything. I just came out and asked him when I saw him next and explained that I'd asked mom and she wouldn't say. Jason always seemed to know that I loved boy's and he said "I like men, men how are like you."
I realized that he meant "sissy panty wearing bottoms?"
I was 15 and all of a sudden I knew why Jason always looked at me so lovingly and developed a huge crush on him. No matter what I did to try to get him to make some sort of pass at me it was like he was a rock dense and clueless. Flash forward to last June when I graduated and turned 18 Jason gave me a private g*ft leaving it in my car with a note in the card with a money g*ft taped to the g*ft box. Inside was condoms to be safe "luxurious panties to attract the boy's" and an "assortment of lubricants for every occasion." He wrote that I was gorgeous and if he was younger he'd be definitely chasing me, my sweet face and perfect boipussy and that now that I was legally an adult to be extra careful.
I took his advice thoughtfully...I got all fixed up in one of my g*ft panty's and called him saying that I was going to pick up a pizza to just hang out.

(1)  (0)
Anonymous

by Anonymous on Jan 24, 2025 at 6:51 PM

My first time was with mom's friend, actually her hairstylist that I was gaga over. I was 15 and mom figured out that I'd been promiscuous with other boy's and wanted me to get the facts about safe sex. There's no easier way to learn than hands-on experiences.

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Anonymous

by Anonymous on Jan 25, 2025 at 1:46 AM

To the second, it's good, too, that you learned from an older man. It was cool of your mom to recognize and acknowledge your sexuality, and try to give you the best opportunity at pleasure. It's just too bad that you had to wait so long.

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Anonymous

by Anonymous on Jan 28, 2025 at 2:42 PM

I never told anyone that the guy living next door to us was giving me money to suck him off and I had to swallow to get the cash. He had a home gym set up in his garage plus some other equipment in his basement, I wanted to learn how to lift and he said he would show me. My mom was like go have fun and he was always super nice to me, one day I am in the basement with him he knew my mom was still at work and he asked if I wanted to make ten bucks. I was laughed and asked if I had to mow his lawn and he literally pulled his shorts down and said no just suck my dick and swallow my load. I did it the first time because I was so stunned by it all but at the same time was turned on for some reason and a few times he had me lay back on a bench and he would suck mine too. Crazy times for me for sure.

(3)  (0)

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