I (25) had impregnated my female boss (32) who is married. [MF]

My boss and I had been fucking over the last year. It started of with light flirting and went to a full bedroom affair. And so did my promotions stuff. Her husband was a busy man and she kinda felt lonely.

We clicked a lot and soon enough I was working on her personal team. Sometimes we’d stay back after office and fuck- having been into swinging for the last 7 years, I loved trying out new things on her. She reciprocated by allowing me to have all the fun we could.

However, by now, I’d become her go to lover and she loved rewarding me for my services, both in office and by letting me fuck her raw. However, one day she had a rather very odd question- since she was trying to conceive with her husband and couldn’t happen, and wanted me to help her out. She essentially wanted me to breed her.

We loved our sexual relation a lot. We were really good fuck buddies. So I decided- why not. We spent an entire week humping each other raw, me dropping every last drop deep in that cunt.

[M]y first webcam show with a hotwife.

In college, all I could think of was sex. I had started webcam shows and enjoyed the attention from cuckold couples and the wives. However, one fine day, one of the regular watchers, a couple, let’s call them John& Jane made an offer- I could fuck Jane on my webcam show.

John&Jane were open swingers. John was in his 50’s and Jane in her early 40’s and loved watching Jane fuck. They had lots of swinger friends as I was introduced to many later on. We decided to do one live webcam show- Jane & I would have a session.

We met in their hotel room where Jane and I decided how to proceed about it. Jane was comfortable showing her face, and I wasn’t, so we decided I’d wear a mask and glasses. We set up our cameras and lights. Jane had let her friends know about our fun so I did expect lots of people to be watching.

It finally came down to the day as I put on the mask and Jane her favourite dress as we teased the camera. We shared an erotic time as she teased a lot. We sat down as we started fucking in front of the camera, and I was suprised by the hits we got.

When I was 18 [M], I had an online hookup to lose my virginity.

This was about 7 years ago, when I just turned 18. Being an adult, all I could think of was sex. So I decided to go to an adult dating and chat site to see if I could get lucky. I uploaded my pictures of myself and my dick and soon enough, it was getting likes from couples and other women. I hit off chat with a few single women, but it was this beautiful ebony that caught my attention.

She was 23 at that time, and I loved her pictures. I have a fetish for women in short dresses and seeing her glossy dark legs in a skirt was a turn on. We chatted casually until we exchanged phone numbers. One day I get a text asking me I’d like to come over to a hotel room to fuck her.

I couldn’t help but say yes. We kept on sending naughty texts to each other, as she talked about the things she’d let me try. On the day of the meet, I make my way to the hotel bar. After a while, I watch this tall ebony make her way to me, exactly like the pictures were and we greet each other.