This all just happened last weekend. I couldn’t wait to tell everyone here about it.
So my wife, Jen’s boyfriend was away last week. Last Friday night we were both off from work, so we decided to just hang out in our backyard and have a few drinks, then fool around.
So it was a pretty warm evening, and we’re drinking beer, just bullshitting. I’m rubbing Jens feet and we’re just playing around with each other enjoying being alone. So we’re getting buzzed and Jen tells me she wants to get me good and worked up for later and she wants me to put on my CB3000. Now I’ve mentioned in other posts that I can’t handle wearing it for long periods of time, usually only a few hours or so. But we were going to get naughty so I figured why not. So I go get it and go into the bathroom and put it on, with a padlock and come out to give her the key. When I come out of the bathroom, she is wearing a pair of sheer black stockings with a garter and patent leather pumps, black lacy panties and a lacy black bra. Out backyard is pretty big and surrounded by trees so it’s pretty private from neighbors prying eyes. She tells me to put my clothes back on (just shorts and a t shirt)
So we go back outside and continue drinking and playing around. A few hours later, Jen’s mom calls her, she’s gotten in an argument with her boyfriend and wants to spend the night at our house. Naturally I’m a little pissed. I was really looking forward to having some really hot sex with her, which I haven’t had the opportunity to do in a while. She tells me not to worry and that we still will.
Now Jens mom isn’t very attractive. She’s about 65 years old and a little overweight. Not absolutely terrible, but I’ve personally never thought of her in any sexual way. Jen and her mom have always been really close. Jens parents got divorced when she was really young and her father was never really in the picture. She’s very comfortable around her mom, and said that she’s not even going to change out of her lingerie., telling me that her mother will probably have a few beers then go to bed. So 20 minutes later her mother shows up. She comes into the backyard and sits down by us. Immediately seeing the way her daughter is dressed she starts saying how she feels bad that she is obviously interrupting, and that Jen should have told her and she wouldn’t have bothered us. We both tell her it’s ok and offer her a beer. She had already been drinking herself which let to the arguement she had with her boyfriend.
So one drink turns into 3 or 4, and we’re all pretty drunk now. It was a really warm night, so Jens mom suggests we all go swimming in our pool. Not thinking that this is a good idea because it’s pretty late, and we are all pretty drunk at this point, I say something like, “we don’t have bathing suits”. Jen comes back with, “let’s go skinny dipping! It’s dark out, no one will see anything”.
At this point I don’t know if she forgot that I was locked in chastity, or if she was just drunk, and didn’t care, but i remained completely aware that I had this large plastic chastity device around my penis.
Being pretty drunk myself, I say ok, fuck it why not. And with that, Jen takes of her heels and her stockings as her mom starts to undress as well. As I said her mom isn’t the sexiest woman ever, but she has large surprisingly perky breasts for her age, and I was also surprised to see that her pubic hair was neatly trimmed and waxed around her bikini line. Jen takes off her panties and bra and they both slip into the pool, as I am taking my time undressing on the deck. Now it was pretty dark, but there wasn’t a cloud in the sky so it wasn’t exactly pitch black out either. So Jen and her mother are in he pool up to their chests, both of their breasts clearly above the water. I bring over another beer for everyone, completely naked except for my cb3000.
I walk over to the pool and they are both looking at me, a naughty smirk on Jens face. As I step onto the ladder, without missing a beat Jens moms notices my cage. “What the hell is that?” She asks drunkenly. Jen laughs, “that’s his chastity cage, to make sure he can’t pleasure himself when he’s not allowed to!” Jen’s mom laughs, oh I’ve heard of these, you make him wear that Jen? Getting over it I reply, only when she’s trying to tease me, ending with a nervous laugh. I start to ease into the pool and as I do, Jen grabs the cage and says to her mother “see, he can’t touch himself when he’s wearing it”, her mother coming over to have a closer look. “Oh man”, I whisper as I start slugging down my beer. Her mother is now fully staring at my penis in this chastity cage, as if her seeing me naked isn’t bad enough. They’re both looking and giggling, and I get into the pool with them.
So now that we’ve gotten that out of the way, we go back to chatting and drinking. Jen and her mom drifting around the pool. Jens mom occasionally bumping a thigh against my cage, and giggling “sorry” when she does. So we have a few more beers and we are all now really drunk. The conversation turns back to my cage. “So you two are pretty kinky?” Jen’s mom asks. To which I reply, “ you have no idea!”
Oh really? She responds. “Yeah, Jen says, he even lets me have a boyfriend” Really? Her mom replies, yeah, but it’s ok, it’s just sex. “Oh, so you guys are swingers”, her mom says. I tell her, we used to swing from time to time, but now Jen just has her boyfriend Jim, and he is enough for her. You’re right, that is kinky! Jens mom says. You want to see him? Jen asks her mom. Sure, she replies. Jen tells me to get my phone. I have a bunch of pics I’ve taken of Jen and Jim together.
Some just R rated, like pics of them naked, or with Jen wearing various lingerie for him, and some xxx rated. I planned on just showing her mom the R rated pics, but being drunk as hell, I forgot that some of the really bad ones were in there as well. As I walk back to the pool with my phone, her mom says “why don’t you take that thing off of him”. Jen agrees, and gets they key, unlocks the padlock and takes this chunky plastic cage off of me. Much better! I say, the both of them laughing. Almost as soon as she takes it off I can feel my penis swelling at how bizarre and humiliating this all is. I quickly get back into the water before I’m at a full erection.
So I open up my phone and go to a folder I thought just had the “r rated” pics in it. Most of them were, pics of Jim and Jen clothed and kissing, some of Jim naked and Jen wearing lingerie and various hosiery for him, I’m holding the phone and swiping to show her mom, “he’s really hot!” She says, to which Jen replies, “and bigger than he is” motioning to me. So I swipe again to the next pic, which is of Jen on her knees deepthroating Jim all the way to his balls. Oh! I uh... stuttering as I swipe to the next one and the next and the next, which I had forgotten were pics of Jim making love to Jen in various positions. Even though our inhibitions were out the window, for some reason I felt she probably shouldn’t see her daughter like that. She played it off like she didn’t really see, but I’m pretty confident she did see enough.
At this point it was getting late, and We were all tired. So we got out of the pool, dried off and went inside. Jens mom to the spare bedroom, and us to our bedroom. We did have sex, but since we were both drunk and tired, it wasn’t as wild as I would have liked it to be. Jen basically just let me get off, and then we went to bed. Her mom had left before I got up, and Jen was already awake as well. Was that weird I asked her, Nah, Jen said, I’m sure she’s seen and done worse.
I haven’t seen Jens mom since then, but hopefully it won’t be too awkward!