A story elaborating on my experiences with my Grandma Gwen of whom the first “ A Different Kind of Granny”, was written about. Helpful but not necessary to read “ A Different Kind of Granny”, first.
3:23 AM. The alarm clock on the nightstand seemed to visually shout at me. I’d been lying there wide awake for what seemed forever. In the midst of the moonlight our four naked bodies lay there so serenely, so in contrast to the lustful behavior we’d relished in a few hours before. Gwen, my grandma, Kylie and Drew, who were swingers my grandma knew, and myself in that king-sized bed fucked, sucked, and played with one another until we were too exhausted to play anymore. But lying there I’d come to the conclusion I’d had enough of living with Gwen. This evening’s activity had convinced me of that.
I couldn’t help but feel strange sleeping with my grandma. Gwen was not only the most sexual person I’d known but also the most uninhibited. She never seemed to have any sexual boundaries besides pain and almost seemed to delight in testing how far she could push mine. I certainly didn’t feel like her grandson. I felt more like her toy. She and I fucked about every other day and I also experienced a few of her friends. They told me Gwen referred to me as the best sex toy money couldn’t buy and I guess I tried to live up to that.
Sometimes it was amazing. When Gwen brought her best friend Dee over we’d take our clothes off. Dee was a chubby gal and a lot of fun and I’ll never forget standing in front of that big bed while Dee sucked my cock as Gwen fucked her from behind with a hot pink strap-on! Later on, in midst of all the action, I felt Gwen seem to make movements to insert the same dildo in my ass, of which I was not comfortable with and told her not to. She’d found one of my limits which she seemed happy to test.
Yes, some of Gwen’s friends were great and some not so much. Chloe, a sixty-something lady who looked every bit of eighty-something would come and Gwen would ask me to let her suck my dick. “Well of course!” I’d reply. I’d take my clothes off and sit back on a chair. Chloe would disrobe revealing a gaunt, emaciated figure with tits that looked like stockings hanging over a curtain rod! She always seemed somewhat miserable which was weird as she’d tell us she loved cum and giving blow jobs. She’d just kneel between my legs and suck away. No head movement, no tongue motion, just sucking and sucking until I came which sometimes took a while as I’d struggle to stay hard, finding Chloe so unattractive. Fortunately, Gwen would sit out of her view and play with herself to help me get off and satisfy Chloe. Also, Gwen’s friend Betsie would visit. Betsie only liked sex anally. She’d jerk off my cock until it got hard enough to put up her ass. Once inserted Betsie would contract her anus, squeezing my penis as though locking it in then yelling at me to fuck her hard. Obliging, I’d thrust my dong as far up her as I could and she’d laugh in joy until I ejaculated deep within her ass! Once satisfied I’d dismount her and she would then take my fresh from her ass cum covered cock in her mouth…strange but weirdly sexy.
That evening with Kylie, Drew, and Gwen thanks to a little pill I’d managed to fuck Gwen and Kylie several times. Gwen was always an animal in bed. Kylie was cute. A very petite 40-something with boob implants two sizes too big, she was very enjoyable. Gwen, being Gwen, told Drew I’d never had a cock in my mouth and she thought I should try it. I looked back at Gwen somewhat annoyed as I’d never really desired such and I knew she was just trying to press my limits once more.
Drew held his erection by the base and asked if I wanted a taste. Almost just to spite Gwen I wrapped my mouth around his 7-inch tool and copied all the action so many women had performed on me. In a few minutes I felt his cock almost pulse then pump globs of semen into the back of my mouth. I continued sucking until his dick started softening as Gwen and Kylie watched. I’d never tasted another man’s semen before that and it wasn’t as bad as I’d expected…not good, but not too bad either. “ Fuck him up the ass, Drew…see how he likes that!” Gwen requested. “I’m not doing that, Grandma!” I stated sternly as I’d experienced an incident that made me uncomfortable with that particular activity. “You know, for such a fun fuck you can be such a little bitch too!” Gwen replied. At first, that statement kind of glanced off of me as we continued with our evening. But as I lay there it offended and hurt me. My grandma, yea she was my grandma after all, saying something so cruel and cold. I’d been with her four weeks until that night and had three left to go until the semester started. I resigned myself at 3:23 AM I’d leave Gwen’s and sleep in my car waiting for the dorms to open. I pulled Kylie off of me gently, showered and left.
In time I’d visit Gwen but never in a sexual manner. She knew she’d injured me emotionally but I also told her I didn’t regret most of our experiences and in some ways I look back at them really fondly as an adventure I’d never dreamt of and probably jerked off to them a thousand times! She would just smile and joke she really wanted to put that strap-on up my ass. I just left it at that….she just always wanted to push those boundaries I guess. She was like no one I’d ever met or anyone I’ll ever meet, I think. She passed a few years ago.
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