I know I haven’t posted a Sunday Session in a while, so this one’s extra special: the time I cucked Nathan with a virgin.
Normally I only choose bulls my age or older, but there was something so endearing about Jay’s PM to me I couldn’t help but respond with interest. He was 19, never had a girlfriend and intrigued by the idea of Nathan letting other men have sex with his girlfriend. I get messages like this quite often, usually it’s someone yelling down from their moral high horse, but this was the first time the disbelief genuinely came from someone who couldn’t understand why he couldn’t even get a woman yet here was another man who was happy to share his girlfriend around.
After a bit of back and forth, Jay very awkwardly asked if I would consider fucking him. If he wasn’t a virgin he was playing the part very convincingly, so even though he was at the time 8 years younger, part of me loved the thought of taking someone’s virginity. I also imagined the level of humiliation for Nathan, for me to cuckold him with a boy who had even less sexual experience than him. Plus I peeked at the pictures in Jay’s gallery and he was cute with a huge dick, which is all I ever ask for.
That night, Nathan begged to go down on me while I described all the things I was going to do to Jay and let him do to me. I was so very tempted, but felt like saving myself for Jay… Well for 3 days anyway. Instead I gave my cuck a handjob, tugging away at his little penis and when his breathing quickened and he started the usual moans before he came, I let go. His eyes opened in shock as his penis swelled a little, dribbled a pathetically small amount of cum before collapsing completely into a ruined orgasm. I kissed him on the forehead and went to sleep while he cleaned himself up.
I normally dress extremely slutty for my bulls, but for Jay I felt like he needed a level of normalcy that wouldn’t make him think he’d just hired a prostitute. So I wore a summery blue cotton dress with little white flowers all over and underneath I wore a white lace corset that was completely see through over my breasts and a white g-string that had a big pink bow on the back. When Jay arrived he brought a bottle of red wine and some flowers. I thought it was adorable but I could see my little cuck’s face growing uncomfortable, as Jay openly flirted as if he was courting me to be his girlfriend.
I quickly moved us to the bedroom and Jay sat on the bed looking extremely nervous. I sat next to him and kissed him slowly, while cuck sat in his usual corner. “I’ve been watching some cuckold porn since you told me this is what you’re into, did you want me to say stuff to embarrass Nathan and stuff?” I laughed and told him to just ignore my little cuckold and pretend he wasn’t even there. I looked over and my little cuck was pulling on his penis furiously at what I’d just said or maybe it was because I laughed or maybe because I was about to fuck someone who’d only ever seen pussy in porn.
Jay and I made out for a while before he shyly put his hand up my dress and slipped a couple of fingers inside me. I moaned, which spurred him on even more as he pushed me back on the bed and climbed on top whilst still maintaining speed. I stopped him when I felt I was getting close and told him to take his clothes off. He kneeled back on the bed, unzipped his pants and revealed a deliciously thick 8 – 9 inch cock that I immediately started sucking on, my ass sticking out with its pretty bow in Nathan’s direction. Jay couldn’t contain himself any longer and came in my mouth after about 5 seconds of oral. Little cuck came over to kiss me but I’d already swallowed it all.
Jay went red and apologized profusely for cumming so quickly, promising I’d only have to wait another 10 minutes and he’d be ready to go again. I forgot that was the benefit with fucking younger guys, some of them have the stamina to cum more than once in an hour. I let Jay give me his first ever attempt at head and it was amazing. I could feel his tongue and fingers pressing and feeling in me, half trying to get me off and half testing to see what would happen if he flicked his tongue a particular way or increased/decreased speed.
In my haze I looked over at Nathan who was mouthing, ‘take off your dress!’ I winked at him and turned my attention back to Jay. I lifted his head up from my pussy and told him to lie on his back. I sat on his semi-soft cock, and rocked back and forth a bit as I lifted my dress up over my head to reveal my white lace corset. Jay reached up immediately to feel my breasts and I could feel him growing hard instantly. I continued to tease him, grinding on to his cock and sitting completely upright so he could only run his hands over my body. I then took his now hard cock in my hand and directed it into me, lowering myself slowly onto it before I started to quicken my motion. I paused momentarily to turn around and ride him in reverse as I faced Nathan who had already cum and was watching me with intensity, biting his lip. All of a sudden I felt Jay’s hands lift me up off his cock and he pulled me forward so that he could eat my ass. I was on all fours and moaning as his tongue moved in and out of me. He then stopped and sat up, “I want to try doggy, is that ok?” I nodded and told him to do whatever he wanted to me. Jay however, didn’t quite know that doggy and anal aren’t synonymous and proceeded to force all thick, 8 unlubricated inches into me. Anyone who’s experienced that before knows it’s not the nicest surprise but little cuck sprung into action and as Jay pulled out a bit, squeezed a big amount of lube on his cock so it started to slide in with a bit more ease. Cuck then lay on his back underneath me so that he could lick my pussy while occasionally glancing at the massive cock penetrating my ass.
It didn’t take long before Jay started breathing heavily and grunting. I let him cum in my ass and told Nathan to remain in position so that when Jay pulled out, his cum would dribble on my little cuck’s face which he gratefully lapped up. As we got dressed, Jay thanked me profusely and said it’s definitely something he’d never forget. I gave him a quick debrief on what doggy ACTUALLY is and he went on his way. My naughty cuck then revealed while I was getting my ass pounded on all fours and he was lying underneath me, he took some photos and a short video on his phone. We spent the rest of the night in bed (seeing as I couldn’t sit properly) flicking through the photos and watching the video. I probably wouldn’t fuck another virgin but I’ve since opened up my age range to younger guys because like I tell my cuck, they just have the stamina to keep me satisfied in ways he never could.