[MFF] The Almost Threesome

I really enjoy this thread and for my first (possibly only) contribution I thought I might write about my craziest sexual experience ever: the closest I’ll ever get to a threesome. This is a long one, as I add a lot of semi-steamy backstory for context, if you want to skip right to the “almost threesome” story then head to the “—-“

A note about me, I grew up in a very religious home, so when I lost a bunch of weight in high school and girls started noticing me, I had a lot of repressed urges and I enjoyed dating around. I didn’t have sex in high school, but I fooled around plenty. One girl, let’s call her Olivia, her and I were friends with benefits. She was a couple years older than me and would give me rides around town. We’d hang out a ton. One day, we get to talking about sex while we are driving around and she’s asking what I have an haven’t done and she can tell I am getting hard just talking about all this. So, she asks to see it. Shocked, but also horny as hell, I resist for a bit but then whip it out. She compliments me for my size (I’m really just slightly bigger than average and a bit more girth, but she made me feel like a god). She reached over and started stroking me there in the car while she was driving and it wasn’t long before I shot all over myself and it was dripping down her hand. She giggled and said, “that was hot!” And thus began our “friends with benefits” stage. We were always there for each other between relationships, but we never really dated.

Olivia has an amazing body. She isn’t athletic, but as cute as could be. She has brown hair and striking green eyes and the most adorable ass. But her breasts were the stars of the show. She was a perfect C cup that bordered in Ds and were perfectly perky.

She went off to college, then I finished high school, and then several years after she finished college and I had gotten out of a bad relationship her and I connected again. It wasn’t long before we were falling back into our comfort zone. Making out, feeling each other up. She would go down on me every chance she got, I have so many stories (road head, dressing rooms, public, etc.)

One night I tell her I’m done with all this messing around, I wanted her. So she tells me to come over and bring condoms. We start to make out before she goes he her room and comes out in the most amazing red lingerie. I almost lose it then and there. Then she lays down and we make out more, our hands exploring each other’s bodies my face in her prefect breasts. She pulls down my boxers and puts the condom on for me, that is when I let her know this was my first time. She was shocked, but I thought she should know. I’d always been too nervous to take that step with any other girl, but I was completely comfortable with her.

She smiled and laid down on her back and guided me in. I am sure I lasted for all of 30 seconds, but even with the condom on it felt amazing. After I finished I went down on her and made her cum. Her little noises got me harder than ever again, when she noticed she sucked on it for a while, but I was so spent I couldn’t even cum again. We just laughed and held each other and fell asleep naked next to one another.

—-

It was a perfect night. But we had made no commitments to one another. Our lives on two different trajectories, we slowly faded apart again after that. Until one day when she called me up to go get drinks with her and a mutual friend, we’ll call her Katie.

Katie and I were friends in high school too. After high school she had put on some weight but was still gorgeous. She had short blonde hair and just massive tits. They were Ds for sure, the type you just wanted to bury your face in.

I was hesitant to meet up with Olivia again, I had been talking with a girl, who I really wanted to date (spoiler alert: this girl would eventually become my wife). But I agreed and they picked me up and we headed to a local bar. We had some drinks and were feeling loose but we were in no way drunk. Then Katie starts talking about how surprised she is about all these friends of ours from high school have been hooking up lately. Then, out of the blue, Olivia say, “you know we used to hook up.” (Pointing at me) I was stunned that she said that, but there was no takin it back now. Katie was just as floored.

“What? I knew you guys like made out and stuff in high school, but y’all hooked up since then?”

“Yeah!” Olivia said proudly as my heart started to pound.

“How’s his dick?” Katie asked

“I’m right here!” I exclaim.

“It’s nice! Not the biggest, but it is really nice. You’d like it!”

At this point I thought I was being pranked. Like this whole bit was planned to see how I would react. But no, Olivia sat there proud and Katie day there curious, both openly discussing my cock in a public bar.

“Did she give you head?” Katie asked me.

“Yeah.”

“And?”

“She’s incredible!”

“Incredible? Really?”

About this time I see the gears turning in Katie’s head. “I wonder if I’m better?” She said with a laugh.

“We’ll get under this table and I’ll let you know!” I said jokingly. Olivia rolled her eyes at me.

“What if we head back to my place and try this out?”

“What do you mean?” Olivia asked, she didn’t look proud of herself anymore, she looked nervous.

“I mean…hear me out…what if we went to my place and both gave him head. Then he can tell us who is better.”

“What?! That’s crazy!” I said.

“How would we do that?” Olivia asked…concern clearly turning into curiosity.

“I don’t know, but let’s figure it out when we get there! Are you in?”

Don’t get me wrong, I was turned on beyond belief. I couldn’t believe this was happening. This is where the comments come in crying “bullshit” which is fine, but this is my one crazy story.

Most of the trip back to Katie’s apartment is a blur. We awkwardly laughed, we joked about who was going to chicken out, my heart was beating violently.

We get to the apartment, we all do a shot of tequila and then head to the bedroom.

“How do we do this?” Olivia asked.

“Well he needs to lay on the bed and you and I need to go in here.” Katie lead Olivia to the walk in closet and closed the door. I heard giggling from them both as I laid there staring out the ceiling, my leg shaking nervously. A few minutes later they came out. Both of them wearing lingerie. Katie was a bit bigger than Olivia but lingerie doesn’t need to fit perfectly to be incredibly hot.

Katie was in a sheet blue lacy bra and panty set and Olivia in a black and white polka dotted teddy. I was immediately rock hard and they noticed.

They both climbed on the bed on either side of me. Olivia kissed me first while Katie rubbed my cock over my jeans. Olivia moves down my neck and Katie started kissing me, slipping in her tongue immediately and biting my lips. Soon I felt a second hand on my cock as now both girls were rubbing me over my jeans. Olivia moves back up to kiss me and Katie moved down and worked to remove my pants. She took everything down at once, boxers and all, my penis springing out.

“You didn’t tell me it was this nice!” She said. I’m sure she was just being kind, but at the time I could have just blown my load at the sound of those words.

Katie started licking my shaft up and down and teasing me, meanwhile Olivia grabbed my ass as we continued to make out. I let out little moans that seemed to incite Olivia to kiss me more passionately, then she pulled away, and said, “can I have a turn?”

“All yours!” Said Katie as she moved up to kiss me. Olivia wasn’t teasing anything, she immediately went to down on my cock and it was a welcome return. She had perfect form, her pace and use of tongue and suction were all amazing. I couldn’t help but moan into Katie’s lips as she kissed me.

Katie pulled away. “This is tough.” She said. “It’s hard to make out with him and know that he is enjoying you more than me.”

“I know right?” Said Olivia.

“How about we take solo turns with him. I’ll go out in the living room, the when you’re done with him, come out and I’ll head in with him.” Katie suggested.

Any nervousness I had was gone. These girls can enjoy me as much as they’d like. I’m just along for the ride! They agree and Katie kissed me and left the room.

Olivia and I were left in the room together, she kissed me and then immediately went back to work sucking my cock. It was the best she had ever done. Warm, perfect, caring, and passionate. I was lasting forever and I don’t know how. I just didn’t want it to end.

The she stopped.

“I think I’m done. Katie is going to have to finish you off. I don’t think I can keep going.”

“I understand, but I wish you didn’t have to leave.” I said as I reached up and grazed her between the legs.

She smiled and said, “I think Katie has waited long enough for her turn.”

She left and I waited in the dimly lit room for a few minutes. Then Katie entered. She stood at the edge of the bed and slowly removed her lingerie. Her massive breasts on full display and her pussy visibly puffy in her excitement.

“You’re cock is really nice you know. And it tastes wonderful.”

“Thank you!” I replied. She smiled and got to work. Her technique was much more aggressive than Olivia’s, but boy could she fit it in there. A few times shoving it to the back of her throat trying to fit it all in, and coming up gasping for air. She would grab my cock hard and stroke it furiously when she needed to rest her mouth a bit. It was becoming obvious to me that Katie liked things a little rougher. I had never been with a girl who like it rough, so I decided to go with it and try some things. I grabbed her hair and shoved her down on my cook and she moaned and whimpered with joy. Then she moved to my side, still sucking me, but shook her ass at me. She didn’t have to say a word. I slapped her ass…well I patted it. I was a bit timid.

“Harder!” She moaned as she pulled away from my cock. So I slapped her ass hard, a red mark appearing instantly. I smacked it a few more times and she sucked he harder each time, that was when I realized I was about to burst.

“I’m about to cum!” I grunted and she just kept going. Humming “mmmmm” on my cock as she went and I let loose the most massive load in her mouth. My cock throbbing with each burst. I spilled out her mouth and dripped down my shaft as she continued sucking. She swallowed hard and proceeded to lick up every drop.

“I’m sorry I didn’t give you a choice. I should have asked where you wanted to cum.”

“Are you kidding me? That was amazing!”

“If I had asked where would you have put it?”

“If I had my choice, probably in your pussy!” I shot back suggestively.

She smiled. “Maybe next time!” She said with a wink.

Katie tossed robe on and in went to clean up. When I came to the living room Olivia and Katie were sitting next to each other on the couch.

“Well?” Katie asked.

“You’re not really going to make me choose are you?” I said.

“That’s why we did this!!” Katie demanded

“Okay, well…Katie made me cum so I guess she wins?” I lied.

Both girls smiled and laughed. We all hugged and Olivia and I left. When we got to my house I confessed that she was really the best, I was just trying to the nice to Katie.

Then Olivia said, “I have to tell you…the reason I didn’t finish was because…I’m seeing someone…I know that makes all of this cheating and this is awful, but I was trying to hook you up with Katie because I knew she’d ‘take care of you’ like I always have…then things got out of control. I’m sorry.”

In that moment I realized…I loved Olivia…and all these years of fooling around and neither of us committing. I had missed my chance.

I told her it was okay. I apologized too. Another lie. I wasn’t okay and I wasn’t sorry. That was our last fling.

A week later I got a text message from Katie. “So I head you told Olivia that she was the real winner. I’d like another shot to prove you wrong.”

But those stories are for another time.

Source: reddit.com/r/gonewildstories/comments/gv2dqy/mff_the_almost_threesome