What's the Best Sex You Never Had?

Have you ever been in a situation where you had the chance to have sex with someone and you decided not to - for whatever reason. Then after the fact, you say to yourself, "why in the fuck did I do that?"

What are your stories?

 

Best Sex I Never Had #1

I was 15 years old and just starting to experiment with sex. Her name was Mary McCarty (not her real name) a gorgeous Irish girl who lived down the street from me. She was 16 and was a knock-out. My friend, who lived next door to her, introduced us. She was very promiscuous. She gave me great hand jobs, loved to french kiss me and let me feel her up (she had great looking breasts). She french-kissed with such a passion! It was definitely x-rated stuff. She had a long tongue and loved to stick it down my throat and then suck my tongue into her mouth. Where did she learn these things?

She would talk to me sometimes about, "going-all-the-way." She invited over to her house one July summer night. Her parents and little brother were gone to the beach for the weekend and she was home alone. It was one of those hot, humid nights in Boston; just perfect for sex.

She answered the front door wearing a creamed-colored, short, silk nightgown. Her sexuality exuded her body. I was mystified, entranced and excited. She invited me into her bedroom. The only light was from her little black and white tv which cast an eiree light over her bed. lThe white sheets on her bed were pulled back. A gentle breeze blew through the window rustling the curtains. I got completely naked and layed down beside her. She kept her nightgown on. We french-kissed and caressed each other. Then, she asks me, "do you want to go all the way?" A thousand thoughts rushed through my mind. Should I say yes? I was a virgin and knew nothing about a women's body or how to make love. Then I thought about my neighbor who got his girlfriend pregant at age 18 and had to marry her. I thought to myself, I don't want to get her pregant and have to marry her, so I choked out and said no.

She gave me a great hand job and that was that. Looking back, I kick myself for not doing it with her. I'm sure the sex would have been great. The best sex I never had!

Spud

 

For me, it was when I was about 21-22 years old. Me and my best friend were dating two very attractive twins. We had been dating them for a few years at that point and had known them since 8th. grade. Needless to say we went everywhere together and had great times. I had seen her sister in her panties and bra on numerous occasions and she had seen me naked when she walked in the bathroom on me during one of our trips to N.H. Although she was a twin, she had more meat on her ass and bigger titties. She looked freakin hot! Well, one night a bunch of us went out to a club in R.I. to see Motorhead and had a great time. My girlfriend wasn't with us because she was taking night classes at the Community College. They had just bought their first house near the beach in R.I. and that's where I was crashing for the night. We got back to the house and my best friend became sick and couldn't stay up, so he went to bed. So, she and I grabbed some hard cider and a joint and headed to the beach. We happily walked the beach, climbing over rocks with me helping her along until we finally reached the far end of the beach. We found a big rock in the sand to plop ourselves down against. We drank our cider and toked up. The sound of the waves crashing over the moonlit beach was very romantic. We sat there and talked about everything. She kept slipping in that she loved me every now and then. I wasn't sure if she meant it as a friend or something more. I do know we were close and I had my arm around her so my hand was basically touching her breast. I gave it a couple little tugs and squeezes and she didn't object. It wasn't as if I was trying to seduce her, but the setting was perfect and so was our jolly moods. She rose up and took her sweatpants off revealing a sexy little pair of white, silk panties. She left her top on. I couldn't believe it. My cock was as hard as a rock at this point. I told her how hot she looked and she just laughed and said "I feel more comfortable this way and besides, you've seen me like this before". She sat right down on my lap facing me, and we proceeded to finish the dube we had put out a few minutes earlier. We gave each other shotguns and she slowly began to rock back and forth over my cock. She said something like " oh, this doesn't look very good, does it?" The whole time this was happening, we didn't really have a care in the world. We were having fun and were pretty fucked up. Just enjoying the moment. I took both her titties in my hands and caressed them. She kept rocking away on me. I couldn't stand it anymore and slipped my hand underneath her and parted her panties to the side. The heat was incredible down there. She was already wet so I just slid my finger inside her and finger fucked her in a rapid "come hither' motion. I popped in another finger and continued on. It wasn't long before she released a gush of pussy juice all over my fingers and hand. It was amazing, but also terrifying. Terrifying because I realized things were getting out of control and I really had a great deal of respect for my best friend. I kept thinking of him and what he was actually doing. Was he still in bed sound asleep? Was he in the bathroom throwing up? Was he feeling better and wondering where the hell we were? She was hell bent on reciprocating to me. She said that she knew it was wrong but she always wanted to fool around with me. We even shared a few laughs about what just transpired. She asked me if she could blow me. I said no, let's call it a night. She asked me if I wanted to fuck her. I said no. She told me she felt bad that she was the only one who got off and just wanted to even things up. I told her I was glad to have gotten her off, but everything was cool. She even tried to convince me to relax, because my best friend was sound to sleep at home. I just couldn't. I felt we had gone far enough and it was time to go. I let her climb up on my shoulders and carried her all the way home. The wet heat from her pussy on my neck was incredible. We reached the house and there was my best friend. Waiting for us! He was still really drunk and wasn't in the best of moods. Our clothes were covered in sand. I'm pretty sure she had a pretty good sized wet spot on her sweatpants. He said things like, " where the fuck have you two been?", "did you fuck him?" He was none too happy. We both played it off by saying that we told him we were going to the beach and that's what we did. She insisted he was being irrational because he was drunk. He seemed to calm down and said "I was just getting ready to go find you two" Had we stayed longer, he would have probably seen his GF blowing his best friend or worse. :toetap05: He went back to bed and I got settled in on the couch. She went in the spare bedroom where they kept the laundry and changed. That's where my overnight bag was. I saw her bare ass leave the room and head for their bedroom. I went in to get my sleepwear and found she had tucker her soaked panties in my overnight. I actually lapped up her juices with my toungue, lol. I put them away and went to bed. The next morning, everything was back to normal. He only made mention of the previous night once more. I just want to end by saying we have never done that again. It's like our own little secret. She also isn't a slutty girl. Besides that night, as far as I know, she has only been with my best friend, now her husband. So, while there was some sex involved, it wasn't true intercourse sex. That's my best story of the best sex I never had.

 

When I was in college my older brother brought home one of his buddies with him one Thanksgiving holiday. We hit it off immediately, and spent most of the holiday together. The night before he left, after everyone else in the house was asleep, I tip-toed out to the living room where he was camped in his sleeping bag, and slipped into the bag with him.

We made out passionately for a long time, and I wanted him very badly. But before he actually entered me, we heard someone stirring in the house and we had to stop. We never got another chance.

He left for overseas not long after that, and was later killed in the Gulf War.

I wish I had been more aggressive inside that sleeping bag.

 

ok that sounds get, but it must have been horrible to hear about his death in the gulf war...

damn that's just such a sad story...i'm sorry

 

It is sad. I don't know if he a chance to be with a woman before he was killed, but I hope so. I wish it could have been me. I wish I had been more aggressive and pulled him inside me .. *sigh*

 

I try not to think it. When I was in my 20's I passed on some very nice tail for various reasons. I missed out on what I'm pretty sure would have been great sex many times over. One in particular was a "good church girl" whose parents I had great respect for, so when she asked me to bang her in her parents bed, I passed. Later I found out that her parents thought I wasn't good enough for their daughter and didn't want her around me because I was a bad influence. I shoulda beat the brakes off that ass when I had the chance. ahh well...so many regrets.

 

Best Sex I Never Had #2

It was in the Haight Ashbury, SF, 1969. I was living in a commune. I was hanging out with a bunch of the family in one the commune houses. We were sitting around in the living room smoking some weed and shooting the breeze. There were mostly couples - I was the only single guy.

Then she walked into the room - a nubian knockout. She was accompanied by another woman who looked like a man-hater. There were few places to sit so the Ethiopian Queen decided to sit on my lap; saying, "oh, I'll just sit here." I was speechless. Joints were being passed around. When it got to her, she put the lit end in her mouth and said, "open your mouth." I obeyed. She blew the smoke into my mouth (called a "shotgun"). I was mesmerized. All the while, I'm looking across the room at her girlfriend who was giving me the evil eye.

This nubian knockout was a fox. She had the most perfect body I had ever seen. She was tall, had long black hair, dark skin and a face like a goddess. I kept thinking to myself, "I want to fuck this woman so bad." I think she had the same thing in mind. We kept gettilng more stoned. I kept looking over at her girlfriend. Her girlfriend kept giving me the evil eye. Then I let paranoia get the best of me. I convinced myself that the chick giving me the evil eye was my goddess' girlfriend / partner and she was jealous. I thought things might get ugly if I fucked the goddess. So, I told her I had to go. She got off my lap, I stood up, walked out the door and that was that.

I look back on it and think that I probably passed up a great opportunity to have great sex. Who knows? We could have been soulmates.

 

does it count when you're so wasted that you cant get it up??

 

In the middle of junior year, already 17 years old and still not a virgin, I went to numerous parties fooling around with guys, but never going all the way. There was this one party an hour away from where I lived out in the country that I went to in the worse of moods. One of those, "I hate men" moods and so I dressed very laidback, told my girl friends that I wasn't going to get drunk and let a man touch me tonight, and that I was just going to enjoy the party and being with my friends. Why my friends didn't point out that the white shirt I was wearing was see through and you could see my polka dot bra underneath eludes me. Anyways, I get to the party and I do that quick scan that I always do to see which men are available and which I want to have. Immediately, I spot Brian playing beer pong. We instantly clicked, but I ignore the feeling and move in the opposite direction remembering the promise I made to myself earlier. I'm just hanging out, taking in the scene, talking to my friends I came with and he walks over and asks if I want to play beer pong. Never played the game before, so he goes over the rules with me and then I beat his drunk ass friend with much pride. The whole time I find myself stealing glances at Brian and catching him look at me. From then on, I'm trying to avoid him, look tough, not drink, exude some sort of "stay away" energy which only seems to be having the opposite effect. He challenges me to a game of pool, I try to refuse knowing that I suck at the game, but he insists I try telling me he'll show me how to play. I don't even know how to position my hands to hit the damn ball with the stick and so he winds up behind me helping me position correctly. This is probably when I start really downing the winecoolers thinking I can at least calm my nerves that way. Miraculously, after his help, I find myself playing pool decently. Feeling the attraction growing stronger between us after the game, I go upstairs to find the girls playing rock band and join them. But the girls suddenly have the bright idea of going for a swim in their 32 degree temperature pool. I have no swimsuit and so I have to borrow the skimpiest of all swimsuits which Brian from the look on his face when I come down the stairs has a feast with. Not having the courage just yet to go into freezing cold water, I stand by the pool drinking and talking to my friend. We start talking about how our breasts look in the bikinis we had to borrow. I say that mine are too small (a fear I've gotten over now) just when Brian walks by. He must have been drunk or really stupid to have the guts to do what he did just then. He said something like no I don't think so, let me see and felt me up right in front of everyone! Then he said they're great. I should have slapped him, but either I was too stunned or the booz had already hit me. I just dove into the ice cold water to avoid him after that. Knowing that he wouldn't come into the pool I taunted and dared him to come in. I was so wrong... he actually stripped to his boxers for me and jumped like a crazy man into the freezing water. Of course he jumped right out, but not before stealing a kiss from me. Now he's telling me to get out of the pool before I catch a cold which I stubbornly refuse to do even though my teeth are shattering like crazy. So that makes him jump back into the pool to pick me up and forcefully pull me out of there. Then he goes find some towels for me to wrap myself in while hugging me for extra warmth. I don't try to pull away, just thankful that he's there. We go back upstairs and play some guitar hero which I'm better at than he is. We drink some more, have some laughs, and I guess I've given in because the next thing I know he's leading me into his bedroom which I don't even try to object to. For the longest time, we just lay under the covers naked sharing body heat and listening to our hearts beat. We talk and he makes this extraordinary effort to listen to everything I have to say about myself and my life. I tell him I'm a virgin (which I was) and do the innocent act that I haven't done much with men before. I also tell him I'm still only 17 and that it would be illegal if he were to do anything with me since he's 22. I also tell him that I'm trying to stay faithful to my boyfriend (and I really did have a boyfriend at the time, but he lived in France). All of these things I tell him don't have any effect on him whatsoever. He starts kissing me sweetly all over my body and massaging my breasts and I start to shiver from pleasure. He moves on top of me as his hard dick slides across my stomach. For a second, I get the feeling he's about to enter me with his motion, so I get scared and pull away. He holds on to me though and gently whispers to relax and assures me he's not going to slide his dick in me. I relax and he continues to move down my body in between my legs to give me the most mind-blowing oral sex I have ever had. I'm panting from the pure ecstacy I'm in. Then he flips me over and we 69, both orgasming in perfect unison. I had decided to save myself for someone who I felt truly loved me (my boyfriend in France). Of course, my first time was not all that I had hoped for. Had I let myself have sex with Brian that night, I might have saved myself from a miserable first time. The good news is that I did find Brian after breaking up with my boyfriend 6 months later and I am now enjoying the bliss I always knew I could have with him.

 

That was a hot story risquebabe. Gave me a hard on Thanks for sharing it and I'm glad you found Brian again.

 

Glad you enjoyed it BostonBill.

 

I'm thinking of starting a new thread where everyone can write about the best sex of their life. I think we might find those stories a tad bit hotter. :drool5:

 

All thing.no kisses ,see vagina,see boobs,and any part of girl body
Help me!!!

 

Lsd sex is the shit. Intense and insane all at once. Once a month we take a trip by ourselves (no one in the appartment ) It can get pretty loud. G/f a screamer . Camping is always a Fun time . Bears ,deer all animals head for different hill. If you want to connect with some one sex up tripp'in.

 

years back I used to have sex with this girl I met at a punk rock bar in Long Beach. I spent the night at her house. She went to work and left me with her mom and then her mom and I fucked for the rest of the day. Her mom was an old school punk. Her daughter was only 15 years younger. She was 22 her mom was 37 and I was 29 at the time. they were both kind of freaky. This went on for about 3 years, unfortunately they were not into doing it with me at the same time. That would have been the ultimate dream come true for me. I was using H and speed at the time and they used to tweak on speed, so we were all pumped up on something. They both happened to get pregnant around the same time but both had miscarriages, probably due to the drug use.

 

Hard to say...one summer in my 20's my gf went on holidays with her family and I didn't see her for 2-3 weeks. When she got back she called me over. Unfortunately her sister and her sister's bf were there too, but it didn't slow us down much. We started making out in the foyer as soon as I got in the door. We slipped into the main floor bathroom and fucked standing up against the wall, her legs wrapped around me. It was short and incredibly intense - and loud. We got out of the bathroom just as her father came in the front door.

 

im working on it..

 

Hey Sith1; too wasted to get it up - yes. Too wasted to go down - never! There are always alternatives in life. Always!

 

unfortunately...i have not had MIND BLOWING SEX...well yet anyway...the most amazing sexual experience i had with a guy didnt involve intercourse...and i havent had sex with him yet, so IMAGINE HOW AMAZING IT WILL BE WHEN WE DO!