Hello,
My bf (32) and I (32) finally did a cuckold/hotwife/threesome/voyeur night! I know I know, sounds like a lot. Let me explain...
For some time now, my bf has wanted to watch me have sex with another guy. I was very hesitant at first but started to open up. We would describe scenarios during sex. We would sext during the day with me using a toy of mine. I'd text him dirty thoughts. I was still nervous though. I asked him if he would be willing to start small at first. He graciously said he was fine going at my pace! So, we both discussed having sex with a guy watching. We discussed me making out with a guy I found online or somewhere other than our hometown. We discussed having sex at a swingers club with no swapping. Many things were talked about, both while horny and with level heads.
After some time, I began to get more turned on by the thought of another guy. I started to flirt while out with my girlfriends. I even danced one night with a guy when I was out with them! I wanted to try the next step. My bf and I sat down and discussed opening up options in case an opportunity ever presented itself. He told me that he was fine with anything as long as I told him the truth and didn't bring home STDs.
I had a work event in Connecticut. It was a conference for continuing education. I didn't need the continuing education myself, but I had other reasons to be there for work. Can't give everything away! I had two coworkers join me, both men. The three of us had most of our meals together. Two nights in, they invited a few other men and women to join us from another state. I became engaged with "Rich" (not his real name). Rich was quiet but stoic. He was funny but didn't need to be the center of attention. He was confident yet easy going. After dinner, we all grabbed drinks. Rich and I chatted about life, our jobs and personal things, even.
I haven't brought up "David" (not my bf's real name) yet in my story. He ended up flying up so we could spend the remainder of the week into the weekend together. Sightsee after the conference. I introduced David to Rich the day he flew in. We ended up having dinner together, the whole group. I noticed that David and Rich really started getting into talking with one another. Both were like old best friends by the end of the night. David and I went back to our room later, and he told me that he thought Rich was a great guy. Before I knew it, David found Rich on Facebook and messaged him to watch sports in our room. Yes, he did ask first, and I said yes.
Rich came up. We all were drinking and Rich blurted out that he found me attractive. The stoic guy slipped up after a few drinks! David said he agreed and I was half blushing half embarrassed. However, before we knew it, the game was over and it was late. Rich left and David and I had the most intense sex! David kept telling me to pretend that he was Rich. I orgasmed a few times.
The next day was the last night of the conference, although we were planning on staying for 4 more nights. I went to the conference, while David went around town. He texted me later in the day asking if I would want to "experience" Rich. I was nervous but actually said yes!
I found out much later that the two of them talked that afternoon.
That night, David told me that the three of us would grab drinks at a local but out of the way restaurant. While there, Rich was stoic but smitten towards me. I was hella nervous!! After some random and needless type of conversation, we went back to the hotel. David invited him back to our room. David, not the best at being discreet, played a porn video on his laptop in the room.
We all were sitting there somewhat nervous. I decided to get alcohol to ease the nervousness. David had liquor so we began to drink. Before I knew it, he and I were kissing with Rich just watching. In fact, David's clothes were off pretty fast. He took off my clothes and I could tell Rich was feeling excited. I gave David a blowjob while starring at Rich. After more foreplay, David entered me from behind.
I was actually having sex with another man watching! After he came, I told David to sit down. I went over to Rich and kissed him. He took control and carried me to my bed. He went down on me like I've never experienced before. I came repeatedly.
Then, we started to have sex while David watched. Admittedly, it was awkward at first but I let my emotions carry over and it became very sexual. After about 30 minutes of David watching, he then joined in. I can't tell you how many positions we tried, but I felt empowered leading everything. It was so amazing. At the end of the night, they both cuddled me.
So that's my story of my first time. Sorry for the length!
Ruth (not my real name :D)
