[M] The first time I had a cock in my mouth to satisfy some bi-curiousity

A few months after my separation, I was starting to pull my head out of the sand so to say. I found myself ready to move on, and after the lockdown forced me to spend months not getting any, I was hot to trot and ready to put myself back on the market, at least for the attention and maybe some action.

I had moved in with my ex-boss, which after we parted ways professionally, she became my best friend. We could talk about anything, she was always super insightful in the ways of life, navigating feelings, sorting out priorities, and was super supportive on the weeks I had my kids and was figuring out the “single parent” thing. As the months went on, we found

Well call her Sherry, she lived in a big ol’ house with her husband Gary, their 3 year old daughter, and a lot of empty space. When I made the decision to separate, she was an extremely supportive friend and also offered to rent me her 3br basement suite for a deal, since I hadn’t figured out what to do with myself. Since our work together ended, I really found she was the friend I felt most comfortable talking to about anything, to be open with, and who had the best understanding of who I was (even when I didn’t know).

Sidenote: she’s incredible sexy, beautiful face, big breasts, curvy in the best possible ways, though asides from a few innuendos and jokes we had never really formed any sexual connection through all of this. I can’t say I didn’t imagine her “writing me up” as her employee, but that’s just me and my corrupted mind hahahah

So a few months into living downstairs, we had found a great groove, we ate together 3-4 nights a week, our kids played together on “dads weeks”, I got to know Gary in a way I hadn’t before. We would hot tub on Fridays after the kids went to bed, go to the beach and river on hot summer days, shared Christmas together. Things were very agreeable and I felt comfortable and secure in a way I hadn’t for years.

I finally got myself out there and tried going out on a few dates. It was great having feedback from both of them, they gave good tips, and helped me shake the nervousness I wasn’t accustomed to feeling. In the end nothing really worked out, more than some enjoyable and memorable hook ups. (Stories for another day)

That takes me to about two months ago. We were fresh out of the hot tub, and feeling the gummies we had all shared earlier in the night. We don’t drink much collectively, but a bottle of wine had been consumed, and none of us were feeling any pain so to say.

We got into the subject of bisexuality, with Sherry recounting a story of college exploration with her female roommate at the time. She’s very unabashed and holds nothing back when speaking, one of the things that makes her such a good friend. Gary had heard the story before, but I hadn’t and I honestly struggled to not pop my towel off my waist as she went through all the details.

She asked if I had ever explored, to which I really had nothing to chime in on. I recalled how I had done some threesomes foursomes, a full orgy, and some partner swapping, but those were the closest I had personally been to a cock. I also stated that while I wasn’t opposed to it, the right opportunity hadn’t presented itself.

She confirmed also that Gary hadn’t had any experiences either, but then giggled and mention that was “despite her efforts trying over the years”. Intrigued, I asked more about “her efforts”.

Turns out on a trip to Vegas a few years past, they had been sitting at a bar on the evening of their last night, and made a bet. They both started with $100 and whoever had won the most by 6am won.

The stakes: a sexual situation defined by the other with seemingly no limits. These were agreed to.

Gary stated he was confident he thought he was going to win. He had plans to cash in and win that prize, but by about 6:45pm he was broke and knew he’d lost. Sherry went on to hit time after time on the craps table and walked away the next morning with $1,380 on TOP of the $100 she started with.

The winner was declared.

Sherry stated that her “prize” she claimed was that she wanted to watch Gary suck another guy off.

At this point, she got into how whenever she watched porn she always started (and finished) with gay porn, as she loved watching two guys together. This was going to be the way she could make a sexual fantasy of hers come true, but it hasn’t worked out then in Vegas or the intervening times.

I didn’t realize that this story would be a segway to exploring this myself. Nothing happened that night, asides from more conversations about sexual escapades, and me having to hear them going to town after we went to bed.

Sidenote: that was seriously fucking hot to hear them after we parted ways. They went at it for an hour and a half, she came loudly at least 6 times and him twice at least. She later acknowledged that she may have been a bit louder than normal on purpose.

A few weeks later, I was at a coffee shop and ran into a guy I know from the gym a few years back. He was the most attractive guy at the gym for sure: half Asian, tall, fair, toned yet lean, long limbed, and a soft voice. Never having been attracted to him at the time, I found with my newfound sexual freedom that I actually felt nervous saying hi to him, and became aware my body language was aligned to more of what I would put out when flirting. Well that was new.

Holy shit did he just smile back at me, then touch my arm?

I asked what gym he was going to, which he now has a gym in his condo. I asked if he had a workout partner, and if he would show me a few things, and seconds later his phone number was in my phone.

I practically skipped home.

Telling Sherry about my meeting, her eyes lit up. She was digging my story, my energy, and was genuinely excited for me.

It was later that evening when the nervousness hit.

Doubts, questions, nervousness! I text Sherry and asked if she was up. She was and was willing to talk. We had a hot tub and chatted more, with her being very supportive. We talked about opening up like this, and she was very encouraging for me to do what I felt comfortable with. I said that I was nervous I wouldn’t be comfortable if things went well, as I didn’t want to initiate something I wouldn’t know I could comfortably do. I thought specifically of putting his cock in my mouth, it turned me on, but made me SO nervous. I asked what it was like.

Sherry has always been very descriptive, and like I said holds nothing back. I felt like she told me about every dick she had blown over the next 60 minutes. She described shapes, textures, tastes, technique. She went over what worked, she shared some embarassing mishaps, and last but not least described the biggest cock she had in her mouth (13 fucking inches long, 2 inches around!! Holy fucking shit)

After we towelled off and were about to part ways, I said I felt better, mostly and genuinely thanked her.

She added before parting that she was glad, and that if I really wanted to feel comfortable and “Mr Attractive” made me nervous, I could always try with someone else first. If I was going to gag, not like the taste, or find it wasn’t for me after all, I’d be better to do it with someone less imposing.

Good advice, as always

I spent a week surfing Reddit, local classifieds, and putting myself out there for maybe a guy looking for just JO buds or bi curiousity. Getting attention on that is like shooting fish in a barrel, but for some reason, nothing clicked.

Friday in the hot tub, Sherry blurted out that she was sorry but she had told Gary about our chat. I was totally fine with that and actually relieved I could talk openly in the hottub with him present. It would have sucked to skirt around that all night.

I shared my experiences from the week, navigating the feelings I had of not feeling safe with this one, feeling another was a phishing scam, and another the guys cock looked like an ugly troll Doll.

Sherry was like: “that’s not the cock you want to put in your mouth the first time”.

Another week went by where the kids were with me so no attempts were made. By the following weekend, I needed to let loose a little so Sherry and Gary send their kid to the grandparents for the weekend and we made plans to go to the casino for the night. Sherry was giddy on the drive over at the prospects of finding me a suitable cock to try out, though I didn’t really believe that was going to be the outcome of the evening. We had a lot of fun, and I joked about how we should try their $100 gamble challenge for who had to do all the hottub prep, cleanup, and towel/robe laundry when we got home….. definitely lower stakes than Vegas.

I tried my hand at roulette that evening and hit on 23 twice, 00 once, and a bunch of outside bets. I easily walked away with about $700 and won the bet handily (Gary got $240 on a slot machine).

We headed home and I got to roll one up while Gary and Sherry did all the work.

When we were relaxing in the tub later, the topic came up about the Vegas bet again. Sherry asked Gary and I both if we had been on the Vegas stakes, what our prize selection would be. Gary said he hadn’t had to declare before, and was hesitant to show his hand, which got him a big razzing from Sherry and I for not sharing. Sherry said I better make my answer good, and after thinking about it, I blurted out how I would have picked watching her suck Gary’s dick, with at least 3 “lessons” along the way. I believe the term I used was that I “wanted to go to blow job school”

A moment of silence followed that made me EXTREMELY nervous that I had just crossed a line.

Did I?

Did I make it awkward?

Did I just ruin my entire “situation” with an offhanded comment?

Oh fuck

Then my heart leapt as she just casually said “oh yeah, we could have done that” like it was nothing, then stated how since Gary had welched on the Vegas stakes it would now escalate to him getting fucked by her with a strap on.

Holy shit did his eyes go wide.

We eventually let the evening wind down, towelled off, said goodnight and headed to our respective rooms.

I was slightly excited at the prospect of hearing them in the room above again, but nothing happened. 20ish minutes later as I was starting to doze off I head a light rapping at the door to upstairs. I let Kara in and she had a look about her. She went straight to it and asked if I wanted to come upstairs to get my cock sucking demonstration. She and Gary had chatted about it, and felt comfortable inviting me into their room, where I could watch her give Gary a blowjob, would work with angles so I could watch up close, and would answer any questions I had along the way. That certainly woke me up. After clarifying comfort and implications I eagerly accepted.

Having been in the hot tub weekly, living in the same house for months, it was nerve wracking to walk into their bedroom knowing what was going down, but I was also surprisingly calm and content. They had a comfortable chair in the corner that was always covered in clothes. It had been turned, uncovered and pulled closer to the side of the bed. Gary was lying under the covers, with only his bare chest showing. He looked good, better than I was used to or hadn’t noticed before, and she poured me a glass of wine and set me up in the chair.

Asking again if I was good, comfortable and still ok to proceed, I smiled and nodded eagerly like a college kid being seduced by the hot girl at school. She smiled and moved herself into the bed on all 4’s and crawled sexily towards Gary. She pulled back the covers, showing his bare body underneath with a solid 7″ hard on raging between his legs. It was a nice looking cock, shaped pleasingly, bush trimmed, thought the dark hairs against his white skin gave so much contrast. He looked at me, we both smiled, then nodded.

She worked her way up his legs and licked her way to the tip, flipping her hair over to the opposite side and locking eyes on my as she ran her hand up, pulling his head into just the tip of her mouth. She didn’t stop eye contact for the first minute and I realized I was looking more at her eyes than his cock. She worked her way up and down the shaft with her tongue and lips, pulling the cock into her mouth from time to time for some long sucks before moving back to work his balls and shaft more. She would stop every few minutes to narrate, ask Gary questions, ask me questions and demonstrate her grip or mouthing and tongue work.

I was floored. It was sexy. It was informative. But more than that, the interaction and stating of feelings and sensations aroused my mind as much as the visual explicitness. Gary was enjoying himself immensely. He challenged her a few minutes in that normally by this point, she would have started fingering herself.

Sherry looked up, and pointedly stated that turning him on and sucking his cock are the HUGEST turn on for her. She gets off on it. But tonight was about me, not her, and that particular line hadn’t been discussed prior and wasn’t open to being crossed.

But she did state “I am fucking wet. Like so wet my panties are soaked, I feel like they would fall to the floor if I stood up. Plus I feel like Gary is going to fuck my brains out after this is all done”

I had pitched a huge tent in my boxers, and wasn’t wearing anything else in the chair. I become achingly aware of my hard on, and desperately wanted to touch myself, but didn’t want to stop the proceedings to clarify, considering Sherry’s statement about herself. So I watched with rapt attention as she continued to work his pole.

When she picked up the pace, I recognized the look on Gary’s face and heard a familiar moan that wasn’t muffled by any floorboards this time, he was close.

She picked up on it and stated she was going to finish him off now, describing the adjustments she was making to grip, suction, and speed, before employing them. I asked if I could move to the side of the bed and he smiled and said yes. I was a foot and a half away as I watched her speed up, bear down and he started writhing and moaning louder. She stopped and reminded him there was no kids and to be as loud as he wanted, he suddenly clued in and got very vocal, explicit and intense in his instructions. He said he was going to come, and she pulled back, opened her mouth and looked straight into my eyes as he shot load after load after load across her face and into her mouth. She fucking drained him, then sucked the last of it out. She looked up at me with her glistening face and smiled.

It was so hot.

After cleaning Sherry up, we all sat on the bed talking about her technique, his experience, my experience and were laughing and joking while we downed the rest of the wine. I commented that I hoped the first cock I put in my mouth was as nice as his, and I swear as soon as I said that, his cock twitched and stood back up.

Sherry noticed too, and pointedly said “I guess his cock things so too”.

Within a few minutes, the discussion quickly changed and after some agreements, Gary was sitting in the chair, with his now-solid-again cock standing straight up.

With much encouragement, and tips, I found myself on all fours at his feet looking down the angle of a dick I hadn’t seen before. It was different from this angle, glistening, with a soft musk and the scent of cum and saliva already on it. I thought of her tips as I worked my tongue to the tip, looked over and said “here goes nothing” before slurping his rod into my mouth.

I think the rest of that night is better served for another story. What do you think?

Source: reddit.com/r/gonewildstories/comments/u9q4rx/m_the_first_time_i_had_a_cock_in_my_mouth_to