This happened in March of 2018
Over many years I’ve had a recurring fantasy about being with men and/or trans women. I would push this away, since “I’m a straight male – not interested in that, and married with a child…” and all the reasons I wasn’t gay. While at the same time, 95% of all my male friends were gay.
Over the last few years, these fantasies happened more often, and stronger. A couple weeks ago, my lovely wife and I had a conversation that changed my life. In that conversation, she helped me come to the realization that I like men and women (and at least trans women, if not all trans probably). She had known for years, but never wanted to push. She told me that while she would support me in exploring this, and I could talk to her about it, she wasn’t interested in exploring it with me. So, I was free to explore outside our marriage.
From this conversation, I felt at ease in a way I haven’t in a very long time. I started watching the things I’d been avoiding for years. I kept checking my reaction to different videos, pictures and writings. Come to find out, a lot of it turned me on.
So I began to want to ‘confirm’ this new me. I felt a mixture of ‘excited at finding a new toy’ and wanting to ‘make up for lost time’. But what if it was *just* fantasy? What if the reality was way different? Well, I decided to so something about that.
I posted an ad on Craigslist looking for a couple that had a bi/gay/curious male for me to learn how to give a blow job. It was my hope to find a couple where the woman had been wanting to watch another man give her man fellatio and was willing to provide some tips and tricks. That had to exist out there, right?
A few days later (after getting many bot responses to my ad) I received a real response. It was from a couple. She had been wanting to introduce another man into their bedroom for 3 years, and her boyfriend felt like he was ready now. I could instantly feel the adrenaline, and my hands got shaky. I replied, feeling both hopeful and scared. We chatted back and forth a bit, and they asked for a picture. I snapped a quick picture of myself waving in the bathroom mirror and smiling – fully clothed. No response for 45 minutes or so after that. I figured they didn’t like the look of me, and decided to move on.
At the hour mark, I messaged them, and asked that if they didn’t want to get together after seeing me, would they be kind enough to send me a dick pic? I at least wanted to see what I’d be missing out on. I mainly did this to see how I felt about receiving one of the most prevalent, and villainized, male pictures in the world since I’d never received one, nor even sent one, before.
She got back to me about 20 minutes later with 3 dick pics, stating that they were still very interested, and this was the dick she wanted to see me suck later that night. I felt the bottom fall out of my world. That sort of freefall feeling you get at the top of a roller coaster right when it speeds down the track. It was hard to believe this was happening.
I found an a alone place (I was at work) and gingerly opened the dick pics. Wow! His cock looked so good, I actually felt like I was salivating! He had a pretty one! I let them know I found his dick “nice looking” then spent a little time with the the pics. A few minutes later they messaged me back, wanting one from me. So, I went to the bathroom stall, dropped my pants, and took my very first dick pic. Ok, I took about 20… I wanted it to look good, and taking them for yourself is a bit difficult, I found out. So, kudos to those that can!
I sent one dick pic, again – my first time doing that (it was a night of firsts). I didn’t hear back from them for about 45 minutes after that. So, my brain goes back to thinking it’s off, and well, at least I got 3 pics out of it.
They message back with face pics of them, saying how excited they are to do this and for me to let them know as soon as I get off work and we’ll chat on the phone to figure things out. My stomach went topsy-turvy again. I was very distracted at work, and am amazed I didn’t make any mistakes. It just took me longer to perform my tasks, because I kept getting lost in my fantasy.
I got off work, called them and we discussed what each side wanted out of the evening:
* I wanted to give a blowjob
* He wanted to give a blowjob and receive one from a guy
* She wanted to see her bf give, and get a blowjob
She wanted to participate as well, including playing with me in addition to her bf, and I told them I was fine with that. So that was all negotiated, they gave me the address. I told my wife what was going on, she said have fun and be safe, and was out the door to their place. We were initially going to meet up at a bar nearby, but due to the weather, and their car trouble, they wanted me to come to their place. I looked their address up on Google Maps, and looked at the street view.
The address was to a Dental office across the street from a gas station. My brain started serving up stories of people being lured to places and killed. I messaged them back that I was uncomfortable meeting them at a dental office, and would be fine meeting them inside the gas station. They explained that if I saw the dental office on Google, they lived in the apartments that are part of the same building, and they were fine meeting in the gas station.
The horror stories my brain served up didn’t go away completely, but I felt safe enough to make the journey. This was the longest 30 minutes of my life. Part of me wanted to turn around, another part of my was still serving up horror stories, and another part was so excited, “I couldn’t stand it”.
I arrived at the gas station a few minutes early, parked, went inside. I thought I should buy something with my debit card, to “leave a trail” in case the authorities needed to look for my body. The bell tied to the door rings, I look over and see the two people form the pics they sent. She walks up, introduces herself and gives me a hug. I feel very relieved, as they seem genuine, and not like serial killers. He and I awkwardly shake hands/half-hug as we’re both nervous as hell. She chuckles a bit, says she can tell how nervous we are, and and leads us back to their place, across the street (“follow me boys”).
She is a whirlwind of excitement. She’s been wanting this for so long, and isn’t nervous at all. She thanks me for not being a serial killer (so it’s not just me) and appreciates that I was totally honest in my CL ad and with them. She got us all sitting down, beer in hand, and we get to know each other for about 30 minutes. Around that time, she starts things, gets us all going, and we have a lot of fun!
She was the powerhouse in the interaction and got everything running. She initially started making out with her bf, and invited me to do whatever I was comfortable doing to her. So, I stroked and caressed her ass and tits, and worked my way around to fingering her. I got her off while she was making out with her bf, and then she started making out with me.
Meanwhile, her bf was going down on her. She worked her way down to start giving me a bj, and invited her bf to join her. She instructed him on what to do, by showing him how to lick me, suck me and play with my balls. He joined in, and for a bit, they were blowing me together. I was concentrating on not coming too quick and enjoying myself. Then he took over, while she licked my balls. This is where his mouth turned into a meat grinder. He was all teeth. We didn’t last long before I had to say something, as the pain was beyond my ability to suppress it.
We took a break. Grabbed a beer, and chilled out for a bit. After that, it was his turn to lie back, and my turn to learn from her.
She took me through the same steps as she did him. The difference was that she said I was a natural. We blew him together for a bit, but then she started working his balls and I was on my own with his shaft.
After a bit, we switched places, kissing along the way, and I began licking his balls. He was moaning and enjoying himself, but then he wanted her to make out with him, which left his dick to me.
I went to town. Licking and taking all of him into my mouth. When his dick hit the back of my throat, it made me very hard. I spent some time with his dick at the back of my throat, enjoying the feeling, and wishing he was another inch or two longer. I would have liked feeling him in my throat.
He got close to cumming, and told me to stop. He wanted to cum in her mouth. So, she went down on him, and I started fingering her again. I brought her off at the same time he came in her mouth. She swallowed his load, then turned around and gave me a wet sloppy kiss. I didn’t get to swallow his load, but I did get to taste him on her tongue.
After that, he fell asleep. She apologized and asked of there was anyway she could make it up to me. So, I asked her to blow me. She got in the 69 position, and I fingered her and licked her clit while she blew me. She came 3 times before I came in her mouth. This time, she didn’t swallow the load, and she kissed me with my cum still in her mouth. We made out for a bit, and then got cleaned up and dressed.
She invited me to come back anytime I wanted, whether her bf was around or not. I told her I’d keep that in mind and that I’d had fun.
I never saw them again, but think of that night fondly.
Source: reddit.com/r/gonewildstories/comments/c12w31/the_first_time_i_m_sucked_dick_mf
Thats a lovely sweet as well as hot story of the evening of firsts. Did that kick off for you more exploration?