[FM] I (25f) slept with my ex’s best friend (25m) while his friends were passed out in a hotel room LONG STORY

This is my first post so any feedback would be welcome. This happened years ago when I was in my 20’s. I’ve been reminded about how many fun stories I have to share and should post some on here. This kind of long but wanted to give some background.

***Background*** My ex and I met on MySpace (what’s that?) after we both graduated college in a true Millennial tale. Social media was fairly new and MySpace was one of the first sites you actually could search people by distance and interests. My ex lived in Milwaukee while I lived in Chicago. While this wasn’t ideal, it was a great relationship, fell in young love, and spent weekends driving back and forth from WI to IL. This was hardly any time to meet any friends that weren’t usually couples since we would be doing couple things all weekend…except for Steve.

Steve was so gorgeous: shaved head, 6’4″, handsome, muscular frame. He wasn’t the typical midwestern farm boy most people assume. He looked a lot like Chris Pine with shaved head and piercing blue eyes. He moved back home to complete his teaching certificate, but he was miserable living at home after graduation. He would go to my ex’s apartment any time he could to get away from the his parents and seeing his students in public.

I always teased Steve that his students definitely were trying to flirt with him because I would have done the same thing. He would say how he would teach me a lesson or two because clearly I’m a troublemaker. This was all very harmless flirting, but there was sexual tension as you’d expect. It was obvious to everyone, even my ex. Steve and I would get along so well we would spend some nights talking all night while my ex went to bed. My ex wasn’t as trusting about the situation and constantly would ask me if we had done anything or hooked up. However, most of the conversation would be Steve telling me how much my ex loved me and how happy my ex is, etc. etc. It was a harmless situation. Steve was a gentleman and I knew I couldn’t cheat on my ex at this point.

Flash forward 4 years…. Steve was living in LA now and single, and my ex and I were completely done at this point (Long distance is difficult kids. Don’t do it, save it for real adults). I needed out of the situation, so I moved out west to begin/restart my single life. Steve and I met for coffee and lunch a few times when I first moved out there, strictly as friends. He knew the whole situation so we barely brought up my ex, other than to say we shouldn’t tell him we saw each other. He agreed and we left it that. We continued to text every so often, but nothing other than “How are you? Hope all is well” texts.

****Crossing the line. (to start)****,,.. I don’t know how it started, but one night Steve and I were texting after a few months catching up. We hadn’t seen each other in a year or so by this point. I found out he had not only one girl, but three different girls he was trying to juggle. He looked so innocent, it was hot to hear he actually was very sexual. The conversation turned sexual, but in the way friends are talking about sex. I didn’t expect to start to get turned on talking to Steve, but I felt myself getting hornier.

“What are you doing this weekend? Hanging out with your ladies,” I teased

“I just got another tattoo, so I’m just going to go home and relax tonight. I can’t have anyone ruining my new tattoo for sex!” he responded

When he got home, he sent me a definite thirst trap pic: him in his underwear shirtless showing his tattoo off. His body was as toned and tanned as I remembered. His six pack and Vline were amazing but he was flexing his arms he was a lot more muscular than I ever noticed. I looked down at the happy trail leading to his waistband, and there was a definite bulge down there. He could say he wasn’t hard, but he definitely was not soft. Fuck he was so sexy, and I would definitely fuck him right now if he offered.

“I know what you’re doing, and I enjoy the view,” I texted him back.

“Your turn :),” he coyly responded.

I wasn’t shy and sent him a picture of me topless in my underwear.

“OMG you’re so sexy. The most beautiful girl I have ever seen,”

“I doubt that, but now its your turn…”

Steve then texted me a pic of his hands down his underwear showing just the red tip dripping with a little precum. I was instantly turned on. I asked him if he was going to show me the whole thing and he did. It was definitely hard and throbbing. I was so shocked he sent it so willingly and fast. Things had escalated from 0-100 in less than 5 minutes.

“This is not how I expected us to catch up, but its been a great surprise,” I said, “Maybe we have to meet up in person soon.” I just wanted to make sure it was clear, I was open to having sex.

“Definitely soon, I enjoyed myself a little too much and going to pass out,” he finished himself off didn’t even realizing I was interested. It was for the best, he was still good friends with my ex, but we crossed a line tonight we probably cant undo. I went to bed, it was a fun story, but didn’t think much of it as we drifted asleep that night.

Steve and I stopped texting mostly after that. I think it was a little regret, but also he started to get serious with one of the girls and didn’t want to mess things up. I was sick of the LA scene and decided to move to Las Vegas to live with my grandparents and brother to get away from LA. I had only been there for 2 weeks, when I got a facebook message from Steve.

“Hey, I saw you were in vegas now?! are you living with your brother? I’m going to be there this weekend with my friends. We’re going to this club on Saturday if you want to meet up!”

I basically had forgotten about the last time we texted, so I was just excited to see Steve. I got ready to meet up with him and his friends that night. I had a fairly conservative dress for vegas clubbing, but I wasn’t expecting much more than to meet up, say hi, have a few drinks, and go home.

I got to the club and immediately started having a blast. Steve and I always had fun because we were just such good friends, and his guy friends were very cool. I was more than happy to play wingman at the club. His friends were getting girls numbers left and right. Steve recently broke up with his last girl, so he even got a girls number. I was getting a fun night out with an old friend. It was just what we all needed.

We were all tired so we went upstairs to their room to order some room service and relax. My brothers condo was on the strip so I had to only walk a few blocks to get home. The two friends passed out on one bed & snoring before food came. Steve looked so tired and I told him I was going to let him sleep.

“No way you’re walking home alone. Its not safe. Have you seen the hangover?!”

“That’s sweet, but its not far and you wouldn’t make it back here alone!”

He conceded that was probably true then his drunk mumbling became apparent when he brought up the ex.

“He would be upset if I let you walk back alone and something happened to you.”

I knew exactly what he meant when he said “HE”, He didnt even have to say his name.

“Haha, he doesn’t care anymore. Its not fair to say that stuff now to him or me”

“You know he got married a few months ago?”

“Yea, of course. People have told me for months. Its life…,” I tried to change the subject, “I heard you were the only single groomsman there. I bet you were popular”

“Everyone was either married to a friend or was a literal child. I was miserable. I thought there would be one single bridesmaid, but she picked old cousins and married friends. She’s not as hot or as fun as you. We tolerate her. No one really likes her”

“How unthoughtful she didn’t think of who you could sleep with in her bridal party on her wedding day. She sounds horrible,” I joked back.

“You two would’ve made sure of that I got laid. That’s why we love you more.”

By this time, Steve is dozing on the bed. And there’s nothing better than hearing your ex’s new woman is ugly and boring. We all love to be that petty. I was quietly getting up to walk back, but I must’ve woken him up as I got up to go.

“10 min, Let me nap and we can walk back. I just need my second wind”

“Fine, I’m just going to lay down too.” I realized how tired I really was after being out all night. It felt nice just to lay down, and I felt myself dozing off slowly.

I wake up a few minutes later realizing I had fallen asleep with my shoes on and jacket. Steve is passed out, I faintly try to wake him and he rolls away from me. I’m way too tired now so I take my shoes off and get into bed now. A few moments later, I hear Steve wake up.

“Are you asleep? I’m sorry I passed out. Do you want to walk back to you brothers?”

“Its fine, Its almost 5am anyways, I can nap here and we can walk back in a few hours,”

“Good, I was worried you’d make me get up im so tired,” he smiled and rolled back over to bed.

Awhile later, I felt him roll back over and place his hand near my shoulder and his head on my back. It wasn’t sexual, it was almost like I was a pillow he forgot next to him holding. It felt nice just to have someone. I moved closer to him so we actually were cuddling and he moved his hand to my waist. We were both sleeping. Innocent cuddling.

“What are we doing?” I heard him whisper to me.

“We’re just cuddling not a big deal is it?”

“We shouldn’t be cuddling.”

“Why? We’ve cuddled many times before as friends and your friends are right there its not like something will happen”

“Yeah, but I really want to touch your body.”

It caught me off guard for a second. Then I brought up our last text exchange.

“I wanted it pretty bad that night, and then nope.”

“Well I felt bad bc Your ex was still trying to get over you..”

I turned over and just looked at him in his blue eyes….and we just started kissing…deeply passionate kisses and holding our bodies close to each other. I could feel his cock grow in his jeans getting hard as he touched me all over my body. We didn’t say anything, until he pulled back and said again, “What are we doing?”

I realized what he was saying…what are we doing? Did we really intend for this to happen? Should we let it happen? I wasn’t sure, but I was willing.

“Do you think we should go somewhere else with your friends there? if we want we can go to the bathroom.” I wanted to clarify that I wanted this to happen and we can make it happen.

“Lets not try to cross that line, can we make out in bed instead.” he responded.

He was such a gentleman but at the same time too gentlemanly. I have basically spelled out two direct times we should have sex and he politely declined. Ugh, he was a great kisser and his hands felt great all over my body.

We made out as quietly as we could for 20 min. We couldn’t stop. He finally pulled back and started to unzip his jeans and he pulled his jeans off I could see his underwear with his huge tent. I was so turned on, but he didn’t want to cross the line, and I wanted to respect his intentions. He was still best friends with my ex, and he didn’t want to betray that friendship. I respected his decision. I still wanted to fuck Steve. I always wanted to. He was sweet and sexy…and he had a way with his hands and mouth…It felt amazing.

He put his hands all over me and flipped me so I was on top laying on him as we made out. I reached down to touch his cock and he flinched and rolled his eyes back. He came back to and started to kiss me again while I gently stroked him underneath his underwear tent.

I was so turned on by this whole situation I was dripping wet into my underwear. They were becoming so uncomfortabl and I had to take them off even if we weren’t going to have sex. I moved off of him for a second, so I could slide my thong off. I felt his hands wrap around my waist, down my stomach, and down my underwear where he slowly took them off for me. We both wanted it, it was only a matter of time

His finger started to slide inside me, Slow and deep he fingered me. We didn’t stop kissing. Our faces just pressed against each other as I was riding his finger. he slid his second finger in and I grabbed his face and kissed him even more. I could be fine with this. He was an amazing kisser, and his fingers were so deep inside me i could feel him rubbing my clit. It was as close to ecstasy as I could feel since we weren’t going to have sex.

I realized his friends were totally passed out. When he fingered me again, I moved my body up and against his tip of his cock sticking out of his waistband. I’m dripping all over him now and i can tell he wants slide inside me. i lift up my dress and he pulls himself out of his underwear and slides it against my body waiting to slide inside me.

“Are you sure we want to do this?” I asked knowing we both did

“Yes, I want to be inside you. Do you want me inside you?” he asked.

I grabbed back and positioned him right inbetween my lips.

“Mmhmm, I do,” as i kissed him again.

The excitement felt great. i slowly slid back on it as he pushed inside me. our collective moan felt loud as we got into motion and our bodies became one. I started to grind on him there while slowly riding. I felt him grab my ass, then my waist , my breasts. I started to feel him sit up. He was kissing my breasts and rubbing my back as I was riding him. His hands were all over my body followed by his lips and tongue. It was pleasure every where he kissed and touched me. I barely had a dress on. It was off my shoulders and basically covering my stomach at this point. If his friends wake up, they definitely will see us having sex, there is no denying we’re having sex at this point, but I’m not going to stop at this point.

“I want to cum inside you,” Steve said in a loud whisper because we were breathing so heavy. He looked up at me and we kissed again.

I was so turned on I wanted to feel it so bad.

“Please cum inside me Steve. I want that so bad,” I felt Steve’s body tense up as he came it felt so good. I kissed his neck and earlobes as he kept pumping into me. He nearly passed out from pleasure and laid there panting.

I fall on top of him and we begin to kiss some more once he catches his breath while he was still inside me.

Its starting to get closer to sunrise now, but his friends are still snoring in the bed. we’re both surprised at what we did, and we got away with it.

“Maybe I should take a shower before I head back. You should get some sleep before you drive back to LA.”

“How about I join you in the shower for round 2?” Steve smiled back.

Source: reddit.com/r/gonewildstories/comments/xdgkl3/fm_i_25f_slept_with_my_exs_best_friend_25m_while