[M] girl[f]riend and her best [f]riend [MFF]

Obligatory apologies for the long backstory. This all happened about 4 years ago when I [20m] was still in college with my first real girlfriend, Tanya [20f] (names changed for privacy). I was her first everything, and while I had technically had sex in high school, it was unmemorable and for all intents and purposes I considered Tanya my first everything as well. Tanya was extremely petite, 5′ tall, slim with a tight body, A cup boobs that looked great on her small frame.

Tanya and her best friend Penny [20f] were absolutely inseparable. I realized super early on that dating Tanya necessarily involved seeing Penny almost as often. They took all the same classes together, told each other every intimate detail of their lives, even slept in the same bed together (Tanya hated her roommates and Penny had a single room to herself. Nothing sexual…yet). This was all fine with me – – Penny and I got along very well and ended up becoming friends on our own. Penny was also fairly short, around 5’2″, and had a more athletic muscular build than Tanya. She had a long term boyfriend all through high school and the first year of college, but they ended up breaking up around the same time I started dating Tanya. She hooked up with a couple people in the first few months I knew her, and I’d always know immediately because she would immediately call Tanya and I over and tell us every little detail. For the most part, she was always dissatisfied and complained a lot about feeling lonely.

Fast forward to about 10 months into my relationship with Tanya. The three of us were hanging out at my apartment, watching a horror (and very darkly lit) show on my monitor. My roommate happened to be out of town that night, so Penny sat on his chair next to the bed that Tanya and I were cuddled on. The show itself was getting very dark and hard to see, and Tanya suggested switching over to my laptop screen and bringing it closer to us. This meant Penny got into bed with us so she could watch too. As the show got more intense, the three of us naturally ended up huddled closer and closer together. By the end of the first episode we all watched on the bed, the three of us were all completely tangled and cuddled together. We ended up falling asleep with Tanya sandwiched in between Penny and I, my leg over Tanya’s, Penny’s leg over mine, and my arm draped over all three of us.

We didn’t really acknowledge the positioning we woke up in, and I dropped the two of them off at their dorm. Tanya kissed me goodbye, and then gave me a look for a second, almost an amused look. She whispered something into Penny’s ear and stepped out of the car. Penny turned red in the backseat and sat there for a second. Then she reached forward, kissed me, and turned back towards Tanya and shouted “There, I did it, happy?” Again, this was never discussed or brought up between Tanya and I in our conversations for the next few days.

The next time the three of us hung out, we were on my apartment building’s balcony with some wine. It was about 1am, but very pleasant out, not chilly at all. I was wearing a tank top and sweats, but the girls were both in spaghetti strap tops and loose fitting shorts (like I said, they were inseparable, even in clothing choices). At some point, Tanya and I started a wine-fueled makeout while Penny sat two feet away from us and looked out over the balcony. That’s when it started.

Tanya: “Hey, you want to try something?”
Me: “Hm?”
Tanya reaches over to Penny and pulls her towards us: “Penny, join ussss”
Me and Penny sorta sit there in a shocked silence for a few seconds.
Penny: “Um, how would this work?”
I snap out of my shocked daze and gently push their faces closer together until they took the hint and start kissing.
Tanya is clearly enjoying the makeout, and takes Penny’s hand and guides it towards my dick.
I was somehow still at around half mast by this point, but the moment I felt Penny’s hand on me, I was rock hard, fully visible through my sweats.
Penny reaches her hand in, takes my fully erect dick in her hand, and breaks out of her kiss with Tanya to do a quick double take (I’m about 7.5″ and fairly thick, and i had a feeling the two of them had discussed my size at some point prior).
Tanya smirked: “Told you”
At that point, Penny and I started kissing while I reached into Tanya’s shorts and started fingering her. Their kissing styles were so different, Tanya was always more gentle and soft but Penny was forward and aggressive. It was turning me on like crazy. I could feel Tanya’s tight pussy tensing up around my fingers and heard her moan. Penny heard it too, because she looked over and saw what was happening with a hungry look.
I had Tanya lie down and pulled off her shorts and panties. She was dripping wet, and i was all too happy to encourage that by teasing her pussy with the tip of my cock.
Penny sat next to her and made out with me while I reached down her shorts and felt her pussy for the first time.

Holy shit. I’d never felt a pussy so wet in my life, and still haven’t since. She was absolutely drenched, and was extremely sensitive on top of that. The moment my fingers touched her, she started writhing and squirming in pleasure, absolutely soaking my hand. I was so turned on my cock was dripping with precum, and I slipped into Tanya’s pussy without even realizing it. I hiked up Penny’s top and started kissing and licking her nipples, which were apparently just as sensitive. She started moaning loudly, right into the open air, unable to control herself. Between Tanya’s tight pussy around me, both girls moaning loudly into the night, and just how hot and porno-esque this whole situation was, I was amazed I didn’t burst immediately. Tanya had birth control but Penny didn’t, and we didn’t have condoms at the time, so I kept fucking Tanya while fingering Penny for maybe ten minutes, during which Penny later told me she came three times. We switched positions a couple times, the first time to Penny with her back against the rail of the balcony, me facing her with Tanya sandwiched between us, my cock in her pussy, hand in Penny’s pussy, and the two of them making out. The second time was back on the bench with Tanya bent over doggy style and Penny lying on her side next to her, in position to both rub Tanya’s clit while I fucked her and to get fingered by me. The two of us made Tanya cum, when Tanya turns around and says “You know what Penny tells me she’s reeeally good at?”

Penny turns red again, but doesn’t say a word. She gets on all fours takes my raging hard dick in her mouth with no hands, and proceeds to give me the best blowjob I’d ever gotten, and the best I’d have for years to come. I kneeled there in ecstasy while Penny sucked me off and Tanya got close to me and kissed my face and nibbled my ear and neck. Not long after I could feel myself about to cum and I tried to warn Penny so she could avoid taking it in her mouth (Tanya didn’t like swallowing so I assumed most girls didn’t). Penny gives me a mischievous look and proceeds to deepthroat me completely balls deep. That was the final straw for me and I came harder than I’d ever cum before all into her mouth. And she loved it. She stayed there with my cock and cum in her mouth, now using her hands to stroke me and get every last drop, right up until I went soft.

We all just kinda collapsed at that point. It was nearly 2am, we just had a loud threesome outside on a public balcony, and we were all too exhausted to even put our clothes back on. We all cuddle together again, and Tanya says out loud what we’re all thinking: “Next time, we bring condoms.”

Source: reddit.com/r/gonewildstories/comments/ffgzlj/m_girlfriend_and_her_best_friend_mff