This story contains over the top sexual experiences, and cuckold/humiliation themes. If either bothers you this probably isn't for you. Everyone is 18+ years old.
I still couldn't believe my luck. As I thrusted inside of my beautiful girlfriend Amanda she was smiling with delight, and a little wickedness, on her expression. She was teasing me about some Instagram photos she had helped some friends take of each other, the benefits of sleeping with one of the photographers was I got the behind the scenes look.
Not just her telling me about her sexy friends, but she even shared some of the outtake photos. Photos discarded for a variety of reasons. But the ones she shared with me were not fit for social media because they showed just a tad too much cleavage, a nip slip, a flash of bra or panty.
This particular session she was turning me on talking about Jessica. Jessica is in her early twenties like Amanda and the rest of her friends. While they all rate as at least cute, Jessica was a stunner. Not an overly revealing dresser, but her undeniable beauty shone through regardless. Brown slightly curly hair, lightly tanned skin that seem to glow. At 5'5 with slim figure and what my girlfriend had confirmed were 34 D's it was hard to believe she was real. If I hadn't spend a few dozen afternoons in her presence, I might not have either.
Amanda was flexing her hips while describing some of the revealing photos of Jessica and taking delight in making me struggle to hold back my load. She knows by openly discussing my fantasies of threesomes or even solo encounters with her friends she can supercharge my libido.
She also knows how much pride I take in being a good lover. I make certain to engage in foreplay, I try and pay attention during sex to every signal my partner is sending. Most important to me I am determined to make my lover cum before I do. Every. Single. Time.
Once we became familiar with each other sexually and comfortable talking about it in detail Amanda and I have discussed basically everything at length. She took it upon herself as a challenge to make me bust before she did. So fuck after fuck she tried new things. She tried positions, lengthy oral, costumes, and even some roleplay ideas.
After hitting all the classics like nurse, schoolgirl, calling me 'master', talking dirty about how much she loved my 'huge cock' (an exaggeration for sure I am 5.5 inches long) she still hadn't accomplished the feat. A few of my suggestions were rejected, for instance she wasn't willing to try calling me 'daddy', rimming me, or letting me give her the first cum facial of her life.
Saying those things were degrading and strong women didn't do them. But one of my favorite suggestions she had taken to with enthusiasm is she always always always announces her orgasms. It is my favorite little addition to our sex life.
Where she found success was when talking about threesomes during sex one night she was describing how hot it would be to see me with another woman, how they would both be sucking me off or even her just watching me, going on and on. But I was going steady, thrusting into Amanda with steady stamina and strumming her clit. Looking between her eyes and her large chest, so big that they nearly hit her chin if I thrust my hardest during missionary, that she hit gold.
She asked me if I would prefer it be a stranger or maybe one of her friends. She mentioned Kayla, a pale very thin redhead she worked with who was known to be a bit promiscuous and bragged about how skilled she was in bed. And my excitement must have shown on my face because she grinned knowing she had me figured out.
Now Kayla is not the first girl id pick to sleep with that wasn't my dear Amanda, but she was certainly hot and her being extra off limits as my girlfriends friend added something extra. This got to me and I pulled out of Amanda to hold off my orgasm.
Sensing weakness she pounced on me, pushing me back, wrapping her huge tits around my cock. Completely enveloping me and continued describing how great it would be if Kayla were licking my balls while I was getting this fantastic tit job. I came spectacularly and it was so good it almost covered the ding my male pride took by finishing before Amanda.
After that she knew my kink and she played on it. We continued talking about it together in bed and we found my ultimate fantasy, being so good in bed that I could please Amanda and a friend of hers at the same time. Making them cum multiple times each before I did.
This was part spawned from my sex life with Amanda, where she confessed that my cock was the best she had experienced and before me orgasms were not a guarantee each session. I was the first man to make her realize she could cum a second time during a fuck.
It didn't happen often, but when she was extra worked up or I was in the zone holding off my orgasm for an extra few minutes she could get there. And the shock on her face when I accomplished it the first time and the way she looked at me like a god was intoxicating. The idea of having that from two women at once was jet fuel to my cock.
Back in the present she was showering me with information about Jessica, how she was newly single for the first time since we had met her and she had gotten in even better shape and was dressing and acting a bit more sexy, as expected post breakup.
Previously good girl Jessica had been a rare participant in the Instagram photo taking of each other that the other girls in Amanda's friend group loved. But the newly single Jessica was now stepping outside of her comfort zone. Showing some tummy and small amounts of cleavage, nothing crazy. But from her it was plenty to make my eyes glaze over with lust.
The beauty of my sweet Amanda despite being an 8.5 to Jessica's 10 on the hotness scale was that she was dedicated to pleasing me and despite all these fantasies and roleplays never doubted my devotion to her. She knew I would never sleep around or be inappropriate with her friends and she never seemed self-conscious about my desires or me leaving her over them.
Truly I had a great thing going. And it only seemed to be getting better because of what Amanda said to me next while I was balls deep inside of her. That a real opportunity for me to sleep with Jessica had arrived.
Now Amanda is such a great girlfriend that she had even floated casually the idea of a threesome to Jessica and a few of her friends before. Even her sweet virginal friend Lisa (22 and still a virgin almost unbelievably these days) had been pitched on the idea that I was a gentle and patient lover and would be a great choice for her to lose her virginity. Unfortunately, none of these had worked out.
Either they were too embarrassed by the idea like Lisa the virgin or were dating other people like Jessica the perfect girl next door and Kayla the serial dating redhead. But the idea had stuck in Jessica's head and now that her long time engagement was over and she was dating again something must have changed.
Amanda explained the situation while toying with my orgasm. She knew that she had my complete focus and that even if this ended up being a lie she could use the pitch of a chance at Jessica to make me cum furiously. But the fact that she was holding off making me cum, she wasn't fucking herself on my cock or moaning like a porn star made be believe this was real and not a tactic. She had saved it for the bedroom for maximum impact.
Jessica had slept with only 1 man until recently, her ex-fiancΓ© had been her first. Her rebound guy, who I had only heard about and not met, was a guy named Ben she met at the gym. Amanda repeated how Jessica was simply gushing about how Ben had opened her eyes in the bedroom and she wanted to keep exploring.
Apparently, this stud, Amanda said stud making air quotes with her fingers, had told Jessica that as hot as she was, he wasn't a one-woman man or interested in settling down and he was ready to spice it up or move along. Which led to us.
Jessica was proposing a foursome. She knew we wanted a threesome with her, and Big Ben (air quotes again) wanted variety. Apparently, he had done them before and said they were always fantastic. I was completely stunned.
On the one hand this was a real offer to sleep with Jessica. I had lusted after for as long as I had known her and who had been the subject of months of fantasies (many egged on by my girlfriend). But I had never considered sharing Amanda or that anyone other than another girl would touch her.
I told her the truth, that I honestly wasn't sure how I felt about that part, but while talking I realized how dumb and selfish that was. I wanted to bang Amanda's friends and she was willing to let me. And I might be so selfish that I would say no because she would touch someone else too?
Unsurprising Amanda is so perfect that she reassured me. She told me that she loved me, and she would put up with having sex with the womanizing dick Ben to see my fantasy come true. As a bonus she said when she made Ben cum quick while I was making Jessica realize what a stud I am, Jessica might want to do true threesomes in the future with us.
Amanda hyping me up and telling me we should do this was all I could handle; I came inside her filling up the condom and realizing it had maybe been 5 minutes since I entered her, and she was nowhere near orgasm. But the look of pride on her face at how happy she had made me outshone any orgasm I had seen her have. How could I not say yes?
Which brings me to today. Amanda and I are standing in front of our couch nervously waiting for Ben and Jessica to arrive at the house we rented together. Amanda all 5'9 of her with her pale skin and dyed purple hair was in a halter top and skirt. A going out to dinner outfit that showed a medium amount of cleavage and a little of her nice legs.
But when Jessica walked in, even with an overcoat on she was glorious. Makeup touched up, hair curled a little extra, and having the face of an angel I couldn't see anything below her neck with the large coat on other than her black heels. I was already growing uncomfortable in my shorts.
Jessica smiled at Amanda, hugged her and whispered in her ear for a moment before stepping in front of me and extending her hand back to the door as if to introduce Ben to us as he came in.
He didn't wait for the introduction, he came in wearing gym shorts and a t-shirt, walked right past Amanda and extended his hand to me. The man was big, just big. I stand an inch or so taller than Amanda at around 5'11, but i was looking straight ahead at his chin, I would guess 6'4. He was a little bulky but clearly not a body builder. Somehow who can move weight around but not some steroid junky.
Ben was smiling big and seemed genuinely happy to be extending a handshake to me. When I gripped it he pulled me in for a one armed hug, "bro" style pulling me in firmly and bumping me off his considerable chest. Ben expressed his gratitude for me hosting explaining that couples new to group sex usually don't host so they can bail easily if they get nervous.
I hadn't thought of that. He also thanked me for bringing the goods and smirked before turning away from me to Amanda. She extended her hand clearly expected a shake, which he grabbed around the wrist, put behind her back, and stepped up to her pushing her against the front door closing it pushing her off balance against it.
Despite her surprise, she was quickly quieted by him putting their lips together and using his remaining hand to push one side of her halter top around her large breast and pop it out. Groping her breast and making out hard her gasp of surprise became silence for some time before some quiet moaning started.
I couldn't look away. The woman I loved, who I shared a home with, who was still perfect and beautiful and 22 years old was making out with the most aggressive and confident man I had ever met. Her eyes wide at first then closing to enjoy the attention.