Note : I had posted the first part earlier but included it in this too so that you can read the whole thing here.
This happened 7 years back. I was a 19 year old engineering undergrad and so was my boy friend (let’s call him Arvind) and his best friend (let’s call him Gaurav). It was a residential college but there was no rampant sex in college as you might imagine because of strict if not regressive rules by the college. Still, I and Gaurav had our fair share of time with each other in lecture rooms at night and rooms in local hotels at times. However, those are stories for some later day. At the end of our first year, in the excitement of getting done with the exam we decided to plan a trip to Alibaug, a coastal place with some friends. Citing a variety of reasons, all of those interested dropped off from the plan one by one and all those that remained where me, Gaurav and Arvind. We decided to still go through with the plan.
To keep the budget in check, we just decided to get a single room. We both were pretty comfortable with Gaurav so didn’t think much of it. Now, I would be lying if I said I had not caught Gaurav staring at me a number of times before that. But we always had a flirty playful relation so we didnt think much of it.
Now, the hotel that we were staying at was connected to a small but pretty empty beach. We reached the hotel by evening. We decided to dump our backs and get to the beach. I had brought along a two-piece swimsuit but wasn’t sure if I was going to wear it because of the crowd. However, seeing the empty beach, I decided to wear it anyways. At the beach, as we got ready to get into the water, I took off my shirt and jeans while the boys also undressed a little. Gaurav was visibly surprised seeing my attire. I am pretty sure I saw something twitch in his pants at that moment. Arvind smiled smugly looking at him.
We got into the water, jumping ino the waves, splashing water onto each other, running around, etc – you get the picture. All this while, Gaurav seemed to have discovered a newfound interest in me for all this time he kept focusing on me : teasing me, splashing water onto me. He kept trying to push the limits to see what all he could get away with. At one point he jumped on me from behind to make me fall into the water. At this Arvind seemed a little tense but he saw me laughing and chilled off. After getting away with it once, Gaurav kept doing it again. Hugging me in different places as he jumped on me. A number of times, his dick brushed against me. To be honest, I was kinda enjoying the attention and kinda encouraging him to go on. By the time the sun was half down the horizon and it was getting dark, we decided to get back to the hotel. Arvind pulled me in for a kiss. Owing to all the tension, as Arvind kissed me, I kinda reached back and gave Gaurav’s dick a tug through his pants, Smiling at him as I kissed Arvind. As we walked back to the hotel, he seemed at a loss of words and rightly so.
Back at the hotel, we showered, had dinner and went back to the room. Not really interested in sleeping early, we decided to play truth and dare which makes for pretty good intimate conversations. We had some drinks and I also wanted to continue what I had started off at the beach…
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So, there we were in the room, spinning a plastic bottle between us. At first, it was the plain non sexual questions for some time, no one choosing dares. But with creeping boredom due to the vanilla questions, the game slowly veered into the 18+ territory
Guarav chose a dare and Arvind told him to go out on the balcony and moan loudly for a minute. He complied. Next, I chose truth and Gaurav asked me my favourite position. Doggy, I said. It’s fast, rough and effective. Arvind smiled smugly knowing how much we like the position. Again Gaurav, he chose truth. I asked if he found me attractive and what was my best feature. He nodded. Boobs, he replied. Arvind was taken aback but then decided to play along, I guess. What do you like about her boobs, he asked. Well, he started, they aren’t too big and from what I can gather they are pretty perky and well shaped. I smiled. Arvind was sitting cross-legged and adjusted his sitting position, which I have gathered with time, is a move to hide a boner.
Next, Arvind chose truth. Gaurav asked if he had sex with anyone other than me. Arvind shaked his head, smiling at me. Next, I chose dare. Gaurav told me to dance on an item song. He put on some cheesy song and I complied. As I danced sluttily, both Gaurav and Arvind were clearly turned on.
After a few more rounds, Gaurav asked me to take off my bra as a dare. I guess he meant for me to take off my top and my bra. But I just reached into my t-shirt and took off my bra, winking at both of them. I handed my bra to Gaurav. Here, enjoy, I said. He laughed and kept it beside him. I’m taking this with me, he said jokingly.
Next, the bottle again stopped at me. Gaurav asked whether there was anything Arvind sexually lacked at. I said that it would be cool to try out a longer penis someday even though Arvind makes up for it with his performance. Gaurav jokingly said well, I definitely have a longer one. I wondered how was he so sure of it…
Gaurav chose dare and I told him to get naked and show me the dick that he was talking about. Arvind seemed surprised but Gaurav quickly complied. With the context of what happened at the beach, Gaurav must have expected that something like this would happen.
As he took off his trousers and underpants, it was clear that he had a bigger tool and his excitement couldn’t be hidden behind a cloth now. His fully erect penis was bobbing in the air throbbing with excitement.
I chose dare. Gaurav gave a funny smile. Give me a blowjob, he said, taking his legs apart and slapping his thighs. I looked at Arvind. He shrugged as if to say, “You’re gonna do this irrespective of whether I agree or not.”
So, I tied my hair in a bun and put my lips around his dick, slowly kissing the head. He had his hands around my hair as he slowly pushed my head down. I compiled and started going up and down on his dick. His hands were now making their way through my top, caressing my back. Just as I felt he was about to come, I took my lips off his dick and told him to come on my face and so he did. Gaurav seemed overjoyed. It was his first blowjob, he said. With a thick load on my face, I again spinned the bottle, resuming the game.
Arvind stopped the bottle with his hand, pointing it at me. Jealous that Gaurav had gotten a blowjob by his girlfriend, he told me to fuck him. Sure, I said, laughing. Arvind took off his pants and mounted me doggystyle. Holding my hair in one hand, he slowly increased his pace. I started moaning. Arvind took off my top and continued plowing me doggystyle. I was now completely naked. Arvind took off his shirt and hugged me from behind, biting my neck, continuing his thrusts. Gaurav seemed to be hypnotized by my boobs which were bouncing forward and behind as Arvind thrusted.
Seeing all this, Gaurav who had just recently orgasmed, got hard again. He stroked his dick watching us. Liking the show? Arvind asked him. Gaurav just nodded. You can touch me if you want, I added.
Gaurav lost no time and started pulling and pressing and playing with my boobs. The bottle was now kept aside. The truth and dare game was clearly over.
I also wanna fuck you, Gaurav said after some time and for some reason, Arvind agreed. Arvind got aside and started stroking himself. Gaurav made me lie on the bed as he lied on top of me. We started playing, hugging and kissing. At points, he was just hugging me tightly or moving his tongue all over my body, kissing me everywhere, flicking my nipples with my tongue, pressing my boobs. It was as if he wanted to try out everything with me. Gaurav said it was his first time. With all his excitement, even I was getting wetter and wetter. He finally penetrated and he surely was big. I let out a squeal.
After some time, laid him on his back and started going cowgirl on him. He was lasting pretty long considering it was his first time. Arvind came watching us.
Finally, Gaurav told me he was about to come. I got off and took his dick in my mouth and in a moment, he unloaded his dick in my mouth. I laid between the boys on the bed, tired and happy. This was my first threesome.
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Next morning, I got up to see that Arvind was still sleeping while Gaurav had got up and was jerking off looking at me. I decided to give him a handjob. While I stroked his penis, he asked if could have anal with me. I hadn’t had anal with Arvind even. But I said whatever and agreed. And so, he applied a very generous amount of coconut oil on my backside and entered me taking my anal virginity. He couldn’t finish since I was pretty tight in my backside as it was new for me too. It hurt since it was my first time but was pleasurable nonetheless. After some time, he just went back to having fun with my pussy and climaxed on my boobs. As Arvind got up, Gaurav proudly told him that he had taken my anal virginity.
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Author’s note : Hi! I’m Padma. I found out about this side of reddit very recently and have decided to share some incidents from my life. I wanted to post this story completely at once but then decided to take my time in writing it correctly in an episodic manner. The first part of story was already posted but decided to include it in this one so that the whole story could be read at one place. I plan on uploading more stories soon. Criticism on scope for improvement is welcome and DMs are open!
Source: reddit.com/r/gonewildstories/comments/na00fs/how_i_f_19_had_sex_with_my_bf_m_19_and_his_best
Truth and dare has always been one of the most popular foreplay for sure?. The entire story was very well written. The build up was certainly the best part✌️ we love reading your content.