[M]y [F]WB ‘opened’ me up I guess

This is a tale about a woman I met during the Pride festival in my town over the summer. If you’ve read my previous stories, you know that I had luck meeting an adventurous woman who turned me onto kinky sex. I also found during our time together that I enjoyed being with guys too. Since then, I’ve been more comfortable in my bisexual skin but I was still intimated by men so I’ve mostly stayed with women.

I met Gil at a cafe during the festival. Gil is not normally my type although she is very beautiful in her own way. I figured her for 10 years my senior so early forties. Very short and very curvy – she described herself later as pleasantly plump.

Siting at the cafe watching the parade go by, Gil opened up the conversation. Her friends had helped to build some of the floats so she came to support. Although Gil wasn’t gay or bi herself, she related to the LGBT crowd. I mentioned that I was bisexual and that I was looking to meet more people in the community. I laughed when she asked me if I had come down to the parade looking for cock. She said it with a devilish grin which captivated me in the moment.

The parade was finishing up so we exchanged phone numbers with the chance we may catch up later. Turns out she texted me around midnight asking if I wanted to meet some of her guy friends. Before I could respond, she texted that she was hosting her annual Pride weekend gangbang. I was taken a back from this. Definitely didn’t think Gil was the type to host gang bangs. I was extremely turned on by the idea but way too nervous and chicken shit to go through with her invite. I replied by text that I’d love to be in the mix one day but way too nervous at this point with people I didn’t know. I got a text from her in the morning asking to go out for coffee later in the week which I agreed to.

When we met up later in the week she told me that she was disappointed I didn’t go but understood as group sex was intimidating for a lot of people. Gil then asked if I would be open to letting her help out and bring me into the fold. I was a little puzzled but she went on to describe what she was about. Gil thought I was handsome but she wasn’t into traditional sexual relationships. Her favourite fantasy was watching men have sex together, especially very kinky and perverted sex. A lot of her guy friends were into the kink scene and were gay so she had lots of opportunities to watch her friends fuck their brains out. Sometimes she got into directing the scene like she was last weekend at her place. There was something really erotic about this older woman who was into some pretty kinky fetishes that I got excited about.

I admitted to her that I had been with a few guys but mostly in threesomes and that I was still nervous being open and sexual with other men. Gil asked me to come by her place after we finished up with our coffee.

Sitting down in her apartment, Gil sat across from me and laid it out. If I was serious, she would help me open up and embrace my sexuality. Sensual domination is how she put it. I was going to be her little pet for the next three months. If I didn’t want to continue, then we’d keep our relationship platonic. Her last request was that I try everything at least twice before I made a decision about weather it suited me.

I told that I thought this was crazy and hot and that I would be into it. I was told to take off my pants, which showed my had cock once my pants hit the floor. Without any hesitation, Gil began sucking my cock. This was the most aggressive blow job I had ever gotten. I wanted to ask her to slow down and take her time. Before I knew it, her finger was slipping into my ass. Everything was moving so fast but I let it just happen. I started to spread my legs a little as her finger dug deeper into my ass, her mouth labouring all over my cock. I think I came after a minute and it was intense.

After I came, I fell back on the couch in bliss. Gil got up and gave me a kiss on the forehead before she went into the bathroom to wash up. When she came back, she had a little bag with her and a TV remote. Gil sat next to me and turned on the TV and played a movie for me to watch. It looked like an amateur porn movie. An amateur gay porn movie to be precise. There was one young white guy bent over a chair while he was taken from behind from a bigger Latin man while also sucking off another white dude. What striked me was that the chair the guy was bent over was in the same room as I was. Gil said this was filmed at the gangbang last weekend. The one I could have come to see. The man in the middle of the threeway was another friend / pet of hers. She asked me which one of the guys would I like to be in that scene. The guy getting his cocked sucked, the guy fucking or the guy getting it from both ways. I was embarrassed to admit but I told her I fantasize about the guy in the middle often. This made her smile.

The bag she had brought into the room was thrown in my lap. Gil told me to put it on and see her twice a week for the next three months. If I made it to the end, she’d arrange a little party to celebrate. I think I knew what type of party she was talking about.

I opened the bag to find a chastity belt. I had seen these before in porn shops but never first hand. Gil picked up the plastic cage and lined it up. I watched her as she squeezed my balls and cock into the device. Lastly she put a lock around the base. Before she closed the lock, she asked me if I was willing to go the whole way. I said yes and then she glossed the padlock.

It felt strange having my cock locked up. It actually made me hornier knowing I couldn’t get hard. Gil said a lot of her guy friends commented on this. Makes men more eager and complacent. She gave me one last errand for the day. Gil slid down her skirt revealing her chubby little body. Gil laid back and spread her legs while I slipped my face past her thighs.

I leave it at this point for now. I’ll write more if people are interested how the next three months went.

Source: reddit.com/r/gonewildstories/comments/754vyp/my_fwb_opened_me_up_i_guess