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My Mom's Boss and I

Posted by: SoloTouchArchive Author: Thomas Age: 44, 42 then Posted on: 27 Jun 2022 2 comments
8 likes 933 views Category: Masturbation Male-Female Tags:

This is my first submission and one of my favorite real life occurrences.
I've been surfing Solo Touch for years and it has served me well. The stories opened my eyes to how much people really enjoy watching each other and has led me to some fun over the years. Recently, after an all-day edging session while reading many stories, I figured it was time to start submitting some of my own. I know a lot of these are fiction but mine are going to be based on true stories and this is one of my favorites. As everyone on this site enjoys masturbating and/or showing off, so do I. This story involves a friend, who happens to be my mother's boss, and me exchanging some 'dirty' pics via phone and sexual chat thru texts and instant messaging. Now this woman, I'll call May, is closer to my age than my mother's so this doesn't involve an older woman fantasy, but I have those stories to tell another time. We are both very sexual people so our stories were quite arousing for both of us and would generally lead to us masturbating on our own. I loved being able to look at the pictures of her tits while stroking (which I still do) and imagining shooting my cum all over them as she has incredible breasts, which I was sure to tell her. She also loved the site of my cock commenting on how big and nice it was, which kinda makes a guy feel good. Our conversation would range from sex, to masturbation and into the realm of sex toys. She would talk about her secret locked toy chest in her room that she would dip into after some of our chats. I made comment to her about how women have so many toys compared to what's offered to men. During one of our conversations she asked me if I have ever used a cock ring, something she had used with past boyfriends. I told her I didn't have any experience with those. One day May informed me she was going shopping for some new sex toys and she was going to get me a gift: cock rings! I told her she would have to deliver it in person and give me some instructions on how to use them properly. So the stage was set! I knew she enjoyed seeing my cock so it wasn't going to be a problem of showing off to her and that was extremely exciting. I could hardly contain myself, like a kid at Christmas! She sent me a text telling me she was done shopping and she would be over in about 1 hour. I was psyched but nervous. I could feel my heart pounding so I chugged a beer to calm my nerves. It seemed to help. So in preparation I lay on my couch, which is situated right by my front door, so when May walked in she would see me laying there stroking my cock. I lay down and started surfing Solo Touch and some favorite porn as I 'got ready'. My favorite stories are about being caught or just being watched..hell, all the stories are good, but those have developed into my favorites. It's actually challenging to try to get hard when you are so nervous but I managed to work myself up to a full blown hard on. I got another text saying 'about 5 minutes out' and my heart started pounding and I thought I was going to cum right there. I returned her text saying, 'just come on in when you get here, I'll be ready'. The adrenaline rush was so incredible I had to stop touching myself. As I got control of the rush, I was able to caress my cock a little bit so I could stay nice and hard for her arrival. A few minutes later I hear her footsteps on my front porch and my heart is pounding again. My cock is hard but not full as she knocks and walks in. I'm lying there in gym shorts pulled down and a t shirt with my cock in my hand, 'hello' I say, 'well hello back', she says and immediately fixes her eyes on my hard dick, which now starts to get harder with her seeing me. (this story has me rock hard again as I type so I'm stroking as I tell it). We joke around a little bit and she sits on a chair across from me in my living room, watching. As she is watching I said, ok, show me how to use these cock rings. She opens the package of 3 different sizes and says, 'you're going to need the big one'. Now I'm no porn star but I guess I'm doing pretty well. I'm 7.5 inches long and thick...about 6 inches around the thickest part. She brings it over to me and even with all my 'begging' to have her put it on she says she can't. If she touches my cock, she'll be all done and won't be able to control herself. I respect that based on some previous conversations we had. She instructs me to put it under my balls and tuck my cock into it. I comply and resume stroking. Now my adrenaline is under control so I start stroking again and I have to say, WOW! As I get harder and harder the veins start pulsing out of my hardening cock and the head starts growing to its fullest size. I look over at May and her eyes are fixed on my growing hard on which makes me even harder. As she shifts in her seat I know she is getting wet. I ask her again if she will help but she again says she can't and just wants to watch. I continue stroking while she watches and makes a few comments about how good my cock looks in the cock ring. As I watch her she still continues to shift in her seat and had to excuse herself to the bathroom for a moment. Now she wasn't gone long enough to get herself off but later I found out she was soaking her panties and had to dry herself off a bit. As she sits back down and watches some more I keep playing with my filling balls and throbbing cock. I alternate between long slow strokes and short quick ones. Precum is flowing from the tip so I smear it around my swollen head and use it as a lube to stroke. This seems to be enjoyable to her as the slick wet sound of my cock is being handled by me. At this point my adrenaline is under control and I'm basically holding back now as long as I can but could cum at any time. After a bit May says she has to get going to run errands. As she stands up and comes over to give me a kiss on the cheek (which I didn't realize that was her intention) and say goodbye, probably also probably to get a closer look, I turned my head and our lips meet and we kiss. Nothing overly passionate but her soft lips on mine definitely pushed me to the next level and apparently her also, as I found out later. As she's walking to the door, I said, 'don't you want to see me cum?' She said 'of course I do' and with that I let it fly... 4 or 5 ropes of hot cum shooting up all over my chest, chin and stomach with intense spasms pulsing thru my body. It was HOT! It was an incredible feeling with the cock ring on and of course with her watching me with wide eyes..did I mention she has big beautiful eyes also? May says, 'very nice!' and we thanked each other as she left. I got a text about 20 minutes later. She had pulled in to the shopping center to go grocery shopping and masturbated herself to an extremely intense orgasm right in the parking lot in a matter of seconds!! HOT! How I wished she would have done it right there for me or told me she was in the parking lot..I would have risked a speeding ticket to get there to watch! We texted some more and of course I told her she should have masturbated with me. Again she said she couldn't have because she wouldn't have been able to control herself and we would have ended up having sex, which she knew couldn't happen. Again, I respect that and was pretty psyched I was able to give her a show that I know she enjoyed just as much as I. I only wish she had at least shown me those beautiful tits and maybe let me cum on them. I'm sure it would have been an added bonus for her masturbating to have my cum all over her tits, but she didn't seem to have an issue getting off without it. Happy masturbating!