Today I was reminiscing about the first time I woke up squeezed, pressed between two hotties. I couldn’t believe that had actually happened to me. I know there are plenty of players who sleep with two, three, or even more girls in one go. But me? Two girls in my bed on the same night?! Heh.
I’m not the "player" type; I’m a total homebody. I’d much rather binge-watch a series and sleep than hit the clubs in South Beach. And when I do go out, I usually don’t pull anyone—it’s sad, but something happened back in mid-2019. All names in this story have been changed, and many details were left out to protect those involved.
It all started when my friend Rick introduced me to Jessica, his girlfriend at the time, at a house party a few months prior. She’s a blue-eyed blonde, average breasts and ass, about 5'3". I don’t believe in that love-at-first-sight thing, but it was as if we’d known each other for decades. She and I hit it off immediately, and she even confessed to me that if she weren't with my friend, she might even date me. From then on, we became very close, which sparked a lot of jealousy in Rick. Their relationship didn’t last long; they were always fighting, and when it ended, Jessica said she didn’t want anything to do with dating anymore (that she was traumatized and all). Except Jessica is a very "proper" girl, or at least that’s who she wants to be. She only has sex with someone she has a serious commitment with. No casual sex with her. At least, that’s how she wants to be seen. She’s a closeted freak, to be honest.
Meanwhile, while Jessica and Rick were trying to figure things out, Diana showed up at my place. Diana was the girl my other friend, Tyler, was into. Tyler and I share an apartment in Brickell and are university students. He was fascinated by Diana, but she wasn’t that into him. It was only through a lot of persistence that he convinced her to stay over at our place. She’s light-skinned, has a slightly larger butt than Jessica, brown eyes, 5'7", and is super bubbly. She liked me right away, but it took me a while to get used to her high-energy personality. It’s funny, but today I love that about her.
A few days later, she grabbed me in the living room while my friend wasn’t looking. And soon after, we started to… and that’s the thing: she already has a boyfriend. Her boyfriend is a "sweet" chubby guy she says she loves very much. I don’t know him personally, only through photos. Let’s just say if Diana is a 9, he must be… I don’t know… a 6.5. She told me he’s a very nice guy and they’ve been together for a long time, but in bed, it seems he leaves a lot to be desired.
The first time Diana and I had sex was thrilling. She was, so to speak, very "deprived," poor thing. It was a show! We had sex for over an hour; by the end, I was exhausted. I’m the kind of guy who takes fooorever to finish. But after the sex, she got all weird and said she couldn’t believe she had cheated on her partner. It seemed like it would be our first and last time, but by the next day, she had already forgotten all about it.
Diana and I started meeting almost every day of the week. We only didn’t see each other on weekends, which is when she stayed with her beloved chubby boyfriend. And it was rare for a day to go by without us having sex. You know, I always worried about becoming a cuckold one day; I always thought it could happen, but I never imagined I’d be the son of a bitch sleeping with the next man's woman. It happened! Though he wasn't close to me. Is it still a sin?
One fine day, Diana and I were coming back from campus towards my building and ran into Jessica on the way. It’s worth noting that Jessica had already split from Rick, who was a close friend. After a brief chat, we invited her to come over for a few drinks and some small talk. Diana and I made a margarita that turned out a bit strong, and then Tyler showed up with a joint that looked more like a Cuban cigar. We talked and laughed a lot. Soon everyone was high and buzzed, as you can imagine.
That’s when Tyler decided to head out to meet a girl he was into. We were rooting for him to get lucky. Well, at least Diana and Jessica were. It turns out he likes to brag about being a player when the girls aren't looking, and that used to make me very envious when I wasn't having the same luck. So much so that it’s still hard to root for him today.
But what made me happy was that it was just the three of us left in the apartment, and when you’re high, you know?, some ideas suddenly pop into your head. Jessica is very afraid of driving home at night, so she decided to sleep over. That’s when I started craving a threesome. But there was a problem, two, actually. First problem: how to convince Diana? Second: how to convince Jessica?
As it happens, Diana was already a little jealous of my friendship with Jessica, and I was afraid she would fight with me over the "indecent proposal." Can you imagine? I could have ended up sleeping alone that night if everything went wrong.
Before fear could paralyze me, I pulled Diana aside and asked what she thought of a threesome. Her eyes widened, and she shot back with a smirk.
"And you think you can handle both of us?"
"Of course, why not?"
"Hahahahh!"
It was easy. She only accepted so she could mock me if I couldn't keep up. Oh, what a girl!
But now I had to convince the "proper" Jessica. I thought she would blow up with indignation when she heard the proposal, but the weed helped, I think. Her eyes widened, her jaw dropped, and she shook her head as if to say, "I can't believe you guys are proposing this to me, you perverts!"
"You don't mind sharing your crush with me, girl? Lol!"
"No, girl, you don’t understand—we want to share you, hahaha!"
"Oh, my God!"
That’s when I remembered Diana had already confessed to me that she was curious about what it would be like to have sex with a woman.
"Oh, guys, I don’t know, I’ve never been with another girl before," Jessica said, already backing off a bit.
"But you liked that kiss I gave you at that party, remember?"
Ah, the party! In fact, they kissed right in front of me. It started with a timid little kiss but then progressed to a more intense French kiss, complete with little moans. But then Jessica went back to being the "proper girl" and didn't want anything else for the rest of the night.
Jessica kept staring at us for a while, thinking about whether or not to accept the indecent proposal. From the expression she made, it seemed like a war was raging in her head between modesty and libido. And the more fluid accumulated down there, and the harder her nipples became, the harder it was to keep the "good girl" under control. The way she pressed her legs together seemed like a last attempt to stop the hungry beast from escaping from between her beautiful soft thighs and swallowing the first cock it found in front of it. It was like those movies where the man fights not to turn into a werewolf, but in this case, it was the proper girl fighting not to turn into the slut. The final straw, which gave the slut the decisive advantage, was when something caught her eye on my pants—it was a bulge that was also growing uncontrollably. Feeling that the war was lost, the saint gave one last sigh and, pleading, asked:
"You have to promise me you'll never tell anyone, okay?!"
After we replied "yes," the war was over!! The good girl raised the white flag. That’s when Diana looked at me as if to ask, "What do we do now?"
"Why don't you two kiss?" I said.
You know that kind of tension you have the first time? That was what you could see in their eyes at that moment. If I asked them to kiss me or even suck my dick, it would be much more natural than kissing another girl's mouth. Finally, Diana took the lead and courageously grabbed Jessica by the head with both hands and kissed her mouth with immense hunger! Immediately Jessica let out a sharp little moan, almost like a little startle, raised her arms in an instinct to defend herself and held onto Diana’s arms for a moment, but then accepted the kiss and began to relax.
I’ve always had a thing for lesbian videos on the internet and could hardly believe I was seeing a scene like this live. As the kiss became more natural, Jessica’s hands migrated to Diana’s breasts and Diana’s grabbed Jessica’s ass.
Then the two lay down on the sofa with Diana on top. She took off Jessica’s top and then her bra. While she kissed her beautiful breasts, one hand invaded the shorts, generating delicious little moans. Jessica’s nipples couldn’t have been more erect—in fact, I’ve never seen nipples like that before; they must have grown an inch, and Diana delighted in sucking those hard nips. Then the brunette went lower and lower until she was face-to-face with the zipper of the shorts, which flew off in seconds. It was the first oral for both of them. Lots of moans and convulsions. While receiving oral from Diana, Jessica didn't stop looking at me. I had already taken off all my clothes and was exposing my 8 inches. Jess’s eyes seemed hypnotized by my genitals for a while, but then they closed in a beautiful moan. Then Diana stood up to take off her own top, bra, pants, and panties and went back on top of Jessica. The two kissed and masturbated each other reciprocally.
It was so beautiful to see the two of them getting it on that I didn't want to interfere. So I sat on the other sofa and stayed there admiring the scene. From where I was, I could see both wonderful asses and fingers massaging both pussies. The whiter fingers massaged the darker pussy, and the pinker pussy was massaged by the darker fingers. The little moans were so wonderful that I actually thought I might be capable of having a premature ejaculation, which made me remember Diana's naughty question "do you think you can handle it? Hahaha!". Oh my God!!
It didn't take long, however, for the sluts to end up looking at me and my succulent dick. They got up from the sofa and knelt one on each side of my legs and started licking my cock as if it were an ice cream. While Diana licked it from top to bottom, Jessica just kissed it with all her love and care. Both exchanged glances with me in that naughty-girl expression and then looked at each other and burst out laughing.
"What are you laughing at?"
"Nothing, lol!" Jessica said while masturbating my dick.
Soon after, she mouthed it and tucked in as much as she could. Meanwhile, Diana came licking my skin from down low up to my nipples. The naughty girl bit my nipple just to pull a contained howl of pain out of me.
"Aaaaiii"
She looked at me and gave that naughty-girl smile. Slut! Not content with that, she came to bite my lips too. I got mad and gave that soft ass a good hard smack!
"Ow, baby!" she said, pouting and wiggling a little. "Give me another one, come on!"
I don’t know, but to me, a smack has to be spontaneous; if someone asks me to hit them, it’s not the same. Suddenly Jessica lifts her head, looks at me and asks:
"Tyler isn't coming back today, is he?"
"I don't know, maybe, why?" I replied.
"Worse, let's go to the bedroom!!" Diana replied, already getting up and grabbing our clothes. They went ahead down the hall to my room. They were laughing about I don't know what; Jessica slapped Diana’s butt on the way... and I followed right behind, fully armed and trying not to pay too much attention to those asses.
Arriving in the room, Jessica lay on the bed face up and legs open for me, displaying her pussy. Diana stayed on all fours next to Jessica, twerking a bit.
"Oh, God, why don't I have two dicks!?"
Jessica didn't waste time and grabbed my dick with both feet making a kind of sandwich, or rather, a hot dog, where her feet were the buns and my cock the sausage. The slut looked at me with a look of desire that almost made me have a premature ejaculation again! From her pussy dripped that viscous liquid that was already smearing her ass and my mattress. She opened her legs and her pussy with her fingers in front of me. I had no choice but to push in.
Meanwhile, Diana sat on Jessica’s mouth with her back to me. The white girl gave a little moan muffled by Diana’s pussy. It was also a moan that expressed a startle; she didn’t expect Diana to do that. I can only imagine the face Jessica made between Diana’s thighs!
As for me, that was paradise! Jessica’s beautiful breasts with their erect nipples combined with Diana’s wonderful ass, all in the same scene! Jessica’s pussy felt virgin, it was so tight. That’s when I started pounding as fast as possible, generating many of those muffled moans from my friend. My beloved friend!!
Diana looked at me with a look of reproach. She didn't say anything, but I understood the message. Her look reminded me once again of that moment when she asked me if I could handle the two of them and also reminded me that there was another pussy waiting for me. It wasn't easy, but I had to slow down the pace.
Jessica was moaning in a way that seemed like she was suffocating between Diana’s thighs.
"Diana, you're going to kill her!!"
"Hahahahaha!" the slut replied! She stood up and turned around. As she turned, I looked at Jessica’s face. She was all red and with an expression that mixed pain with pleasure. Her eyes seemed to beg for mercy, her brow furrowed and sweaty looked like someone suffering, but she didn't seem to want to give up, quite the opposite. Then Diana went back to sitting over Jessica's mouth, only this time she was facing me. We kissed for a while; you could see Jessica's tongue was working on Diana's pussy and this was driving her wild. She came shortly after in one of the most beautiful moans I’ve ever heard.
After coming, she lay down next to Jessica on her stomach, showing all the beauty of that soft ass, those toned legs, and that smooth back. Jessica continued with that enigmatic expression and now dug her nails into my chest. She came next, writhing and moaning so loud she must have woken up the whole neighborhood.
But I wasn't finished yet. While Jessica relaxed her whole body like someone who had just finished running a marathon, I went to mount Diana. The first slut had already succumbed to the power of my cock, now the other one was left.
Diana did little, just lifted her butt a bit so I could fit. With both hands, I separated her cheeks and saw her asshole and her pussy a bit lower down; I positioned the head of my dick at the entrance of her slit and pushed in. She moaned beautifully, her hands gripped the pillow hard and her breathing quickened with every thrust of my dick. Lying on top of her, I grabbed her hair, making the naughty girl moan even more.
Suddenly I felt Jessica smack my butt. I didn't even notice her getting up to do it. That's when:
"Hey! What are you doing!!???"
The slut stuck her finger in my ass without even warning me or asking if she could! I had never felt anything inside my tail like that before. I don't know how to describe the sensation, but I know it drove me almost crazy.
"It’s good, right?" Jessica said.
"Holy shit!" I replied!
That finger in the ass was a low blow in every sense. I was winning against the two of them, I was handling it, I was the only one who hadn't come yet and I had the breath to fuck much more, but that damn finger had the effect of making me come almost instantly. I was a bit mad for being invaded like that, but on the other hand, a finger in the ass is like a rock of crack—once you try it once…
Afterward, we went to the kitchen to eat something and soon after we went back to the bedroom to enjoy some more. The girls were very excited, laughing at anything and very cuddly too. Soon we were all kissing again and rubbing our bodies. This time Diana was the first to take the cock in her pussy. She was on all fours taking slaps on the ass from both me and Jessica. Then it was time to switch. When I was already positioned behind the blonde, she said:
"Hey honey, don't you want to eat my little ass?" Jessica said, almost purring.
Diana, on the other hand, looked surprised and couldn't help but ask:
"You like giving your ass, girl? Are you serious?!"
"You don't? Oh, it’s a delight!!"
I couldn't see my own face, but I’m sure many hearts came out of my eyes seeing Jessica say these things!! It was further proof that behind that "proper girl" facade was a monster freak. Diana made an "ooh!" face, the kind that says "it hurts just thinking about it!!"
While Diana spread Jessica’s cheeks with her hands leaving the asshole exposed and looked at me with a naughty face, Jessica said, purring:
"Slow!"
You can't imagine how hard it was to push in slowly! God, give me strength!! First the head went in, obviously, and then she gave a little wiggle. Good Lord!
"Oh, slow!!" she said looking back with a poor-thing face. I thought she was messing with me, so I pushed a bit faster. She threw her body forward to escape.
"CALM DOWN, MAN!!"
At this point, Diana was right there sitting on her own feet watching us with wide eyes.
"Okay, okay, my bad, sorry! It’s just hard!" I replied anxiously. That tight little hole felt like, hmmm. That felt like an eternity! Half was already in and the naughty girl was teasing.
"Put it in with care, Marc!"
What agony!! Only 1/4 of the cock was left out.
"Can I put it all in now?"
"CALM DOWN. After it's all inside then... AHH! HMMMM! Delight!"
"Then what?" I said almost insane!
Ready, my whole dick vanished inside that butt. Now?
She started laughing and then said:
"Go deep, you sexy thing!"
So I started the back and forth.
"Faster!"
I grabbed her waist and released all the wrath in that little ass.
"FA... AA... ST.. EER.. R... OOO....UUUUU... AH!"
She grabbed the pillow, hugged it, bit it, and moaned like never before. She didn't remind me of that Jessica from the beginning in the slightest. Then she came, lifted her head and:
"AAAAAHHHH, AAAAHHHH, AAAAAHHHHH, MY GOOOOOOOD!"
Diana ran to cover the other one’s mouth; it was already 3 in the morning! I don’t even know how the condom didn't explode! It was pure cum. After that, we slept until they knocked on the door to see if we hadn't died.
