You are here

[M]y first time and I got to sample both sides: The Plan. | 2016

I know, I know. Reddit hates multiple part stories. Well sadly I did not want to overwhelm you with text so I had to split this up into 3 parts. I will post them throughout the week. This is my first time posting and I hope you all enjoy it as much as I did doing it. This story does invlove group sex, and will have some homoerotic moments as well. Also I was fairly drunk when it happened so please forgive if I skip some details. Names have been changed to protect the not so innocent.

I never was an adventurous guy… I would never really go out and party or anything like that so it should not be a surprise that I never really had a girlfriend and kept my virginity for awhile. It really was not until I left high school and started working at an animal shelter that I met the three people who would bring me out of my shell. Their names are Jenny, Joy, and Blaine.

Jenny was a fit, tall, blonde girl, with an amazing ass and about C cup’s. Joy was a short but still fit girl with long fire red hair, and about B cup’s. Blaine was not a large guy, roughly my size at 5’11 and 150lbs of muscle (I’m more of just a skinny kind of in shape physique), the only difference between the two of us though is I have medium brown hair, whereas he had a shaved head.

These three had been friends for quite a while before I came into the picture so they knew each other quite well… turned out they knew each other much better than I thought. It would appear to the naked eye that Blaine and Jenny were an item, but it turns out the three of them were involved in a FWB sort of deal. Never have I been so happy to be apart of a group of friends though.

It was a night after closing the shelter that three of them decided to go out for drinks. I put up a list of excuses as to why I couldn’t go, but they systematically tore every one of them down. I tried to think up more, but the next thing I knew we were already across the street at the local pub and Joy was bringing us shots of god only knows what. We got to talking about general stuff, what was going on in the world and everything, we even dove into some sports topics (not a topic I am terribly knowledgeable at); several shots later it led to us discussing our personal lives. This is where I learnt of their sex triangle. Eventually, it led to Blaine spilling his secret of how he always wanted to be with a man just to try it out.

“Oh! Well, you know Ted is not only a boy but also pretty attractive one at that!” Joy yelled in her typically oblivious fashion.

I was worried that they were trying to set something up, I had no idea if I even liked men considering I had not even been with a woman yet.

“Well… I don’t quite know if I would really be the best option for that.” I said awkwardly.

“Why not?” Joy asked, tilting her head like a dog trying to understand why master hadn’t thrown the ball.

“Because I am… well… I am still a virgin.”

Everyone let out a gasp as if this was the biggest shock of their lives.

“No way! How are you still a virgin? I thought the girls would have been all over you in highschool.” Jenny yelled; her volume control going completely out the window when she drinks.

“I wish.” I replied sheepishly, my brain screaming at me to get out of this situation now.

There was a bit of silence after that. I could see the three of them eyeing each other as if they could read the other minds. Finally, Blaine got up and strolled up to the bar to get more shots.

“You know Ted, we have a bit of a crush on you.” Joy says as she pulls me closer into the table. “And by we I do not just mean Jenny and I. Blaine does too.”

“Oh.” I replied a little too loudly. I had always thought of being with a man, but I wanted to be with a woman first.

“Yeah, we do. Why don’t you come back with us and not only can you lose your V-card, but you can sample both sides of the spectrum?” Joy whispered seductively in my ear… well as seductively as someone with her blood alcohol level can be.

‘I don’t know… I have never really…” Jenny had cut me off with a glare of determination.

“I’ve seen how you look at us. You have no choice but to come back with us.” Jenny yelled louder than she needed to.

I was in a bit of a shock so my words lost me, and the alcohol took control so I just nodded my head and blushed. Blaine showed back up with some drop shots for us.

“Cheers! To a very eventful night.” Blaine lifted his drink and we all clinked and took the shots.

It did not take long to get a taxi, and seeing how we ended at Blaine’s house he payed for it. We all got settled in his living room, he had a dimmer switch so it was quite… well ambient to say the least. Blaine pulled out a bottle of rum and we all sat on the ground taking shots. The three of them regaled me with stories of what they had done together, and I could feel myself getting quite horny.

“Oh look, we aren’t even half down the bottle and you are already ready to go.” Joy laughed as she crawled over to me. She slowly peeled off my shirt and started undoing my pants. I could see Jenny and Blaine stripping each other in front of us, both of their eyes fixated on me.

“I’ll give you one chance to back out of this. If you do not want to then just push me away, ok?” Joy said in the first serious voice of the night.

I just nodded again, words had escaped my melting brain. Joy proceeded to strip my pants and boxers off. My heart was racing, I had no idea if I was ready, but I knew I wanted it.

“Oh, you're a lot bigger than I thought you were. This is going to be fun.”

Joy began to slowly lick my cock, her fiery red hair somehow staying flawlessly out of the way. Jenny had dropped to her knees and was well into blowing Blaine.

“Mmmm now I’ll let you cum once before we get started. That way you will last longer with the rest of us.” Joy said as she took a quick break.

It was amazing, this was the greatest thing I had ever felt. I felt like my heart was going to explode from my chest… and well I felt something else going to explode as well.

“Oh Joy! I’m going to cum!” I yelled as well as my slurred words would let me.

She just continued sucking, her eyes making direct contact with mine until finally my dick exploded and cum shot out into her mouth. I thought this is where she would finish but no… she just kept sucking until I was completely dry. Then finally she pulled off and swallowed.

“Mmmm, and you taste good. I like you.”

“That was incredible…” I was out of breath and was having a hard enough time already squeezing out words.

“If you think that was great, well just wait until you try pussy for the first time.” Joy looked sheepishly at Jenny who had just finished Blaine. Rather than swallowing, she let him spurt cum all over her tits.

“Hehe, I cant wait to try you on sweety.” Jenny said as she rolled her hand down and started stroking her pussy. “And I think you are going to like what we all have to offer you.” She licked her lips and gave Blaine a quick glance.