How the Best Sex of [M]y Life Led to the Most Frustrating Night of My Life | 2016

I had been dating Rachel for a year. It was a whirlwind relationship. We were extremely close and intense until it all burst and consumed itself. But before that, during better times things were glorious.

We were in love with each other because of our differences. I am soft spoken. I let my presence speak for me. She was quite the opposite. Outgoing and outspoken she got energy from being social. Always. She needed new like no one I ever knew. She needed constant stimulation. Besides me, she could only be close to a few people because they frankly couldn’t handle her.

This is why I was surprised when she let her new friend, her soon-to-be best friend move in. Rachel met Regan and things shifted. They got real close. Again, interesting because they were so opposite. Not in personality, but in temperament and appearance. Rachel was a tall girl (5’7”), very thin (105/110 lbs.), perky breasts, tight, tone, perky ass soaked by California sunshine. Regan was from the Midwest, short (5’3”), and very large breasts. She was in shape, but she wasn’t thin in the same way. She was gorgeous, like Rachel, but in her own way. More than that I really liked who they both made each other. As friends they made each other better and that’s a great thing to see when you’re in love with someone. They were inseparable.

That is what made this particular Saturday night out peculiar. We went out five or six nights a week. All the time. And always together. But tonight Rachel said she didn’t want to go out. Rachel promised Regan we’d go out if she felt up to it. Five minutes after Regan ceded the nights’ plans and headed out on her own Rachel was on her bare knees on the living room floor. No regard for herself. Her mouth was opened wide and full. Her best friend had barely shut the door before she engulfed me. It’s not that I didn’t necessarily expect something like that because she was normally happy enough to fuck a few times, go out and fuck again later. It is that all of the drama beforehand wasn’t necessary. We had fucked and gone out many times before. So I was slightly confused. Delighted for sure. But, still confused.

Two hours later and I understood more. Tonight was different. Rachel hadn’t been like this before. I mean she gave herself over to me in every possible way a long time before that night. But she was on a new level. She ached for it. Craved it. She’d been known to get drunk on dick, but she was practically out of her mind.

Rachel’s fiery personality was both fueled and tamed by our sex life. She hadn’t been with someone like me before and she loved it. The first night we slept together I went through an entire pack of Magnums. When people tell you that anyone can fit into a condom what they leave out is the word “comfortably.” I had never found a condom to fit into without feeling like I was being strangled. That’s not a great feeling, and it hurts blood circulation. I broke through the last condom with a thrust. She felt my raw head in her and wouldn’t let me take it out. We fucked for a few more hours. She came a half dozen times. I came inside her twice that first night. She wasn’t on birth control then.

So consider that context when I describe her on this Saturday night as being on a previously unseen level.

She sucked, squeezed and slapped my heavy cock around for quite some time. I could feel my balls pulsate. They were swollen and warm. She was attempting to cup them in her left hand as she stroked and sucked with her right, but gave up almost instantly and instead used both of her hands to stroke as much as she could grasp while coming up for momentary air. I knew I had to stop her or I’d cum. I lifted her chin, she pulled back slowly and wiped drool away. As she gasped for air I picked her up, kissed her and placed her on the kitchen counter. As she opened her legs wide, I wiped the streaks of cum connecting her thighs back into the lips of her pussy. I kissed her pussy lips softly in appreciation and then spread them wide and kept them parted with my tongue. I took her to and brought her back from the precipice of cumming three or four times. Each time edging her slightly closer, but never allowing her to go over. After the fourth time she finally pushed me off in playful anger. She faked a temper tantrum and went to the couch. I placated her. I told her I was sorry for being mean to her. I went to her sitting on the couch and got on my knees in playful surrender. She smirked. I spread her knees open and lifted my head to her nipples. I kissed her right nipple gently. Then I kissed the left. I started sucking her left nipple as she moaned. I took her entire breast in my mouth while I rolled my tongue back and forth flicking her nipples until letting enough cold air in my mouth to surround her breast and just like that pushing the cold air away as my warm tongue engulfed her breast again. I alternated like this as she moaned in relief. I teased the edge of her right areola with my cold breath and nipped at her nipple playfully. I repeated on the right what I just did with the left. She lifted her knees to me and grabbed my head with all her might as she ached. She wanted me inside of her. I pushed her back. And went back to the left breast. And then the right and back and forth for 20 minutes. By this point her hands were pulling my hair. She was already soaking. But now, she was actively dripping down her inner thighs, inbetween her cheeks and asshole, spilling out. So I looked at her and stopped. And as she caught her breath I took her breast back in my mouth. Her dripping was now a stream as she had her first orgasm of the night. She ruined her middle couch pillow. I hadn’t even been inside of her yet.

She continued through her orgasm holding my body tightly. She reached down for my throbbing penis. I pushed her hands away. She rolled her eyes and went into her roomate’s room and shut the door. I opened it. She told me to get out, that “this isn’t even my room.” I told her that I didn’t think Regan “would mind me inside of her private areas.” I knew this would entice her.

We all flirted together nearly the entire time we knew each other. Regan would walk around in silk robes without a bra. Rachel would joke about my “big fucking dick” and say things to Regan like “oh, he thinks because he has a big dick he can say whatever he wants” in playful anger. Regan liked the dance. Rachel loved it. I was obviously eating every fucking second of it up. Earlier that day I was getting my laundry from the laundry machine and had shorts on without any briefs. I usually don’t do that for obvious reasons. So Regan sees me walking and says, “God make sure you don’t catch that on anything. It’s just swinging everywhere. You might hurt something.” She giggled. I was rock hard and quickly dashed to Rachel’s room. I told Rachel that a few minutes after it happened and she smiled wide. So I knew this would entice her and it did.

She took a step forward and looked me in the eye and said, “You want to fuck her, don’t you?” I looked back and without breaking gaze said “Yes.” She replied, “Show me.” So I took her by the throat, turned her over and pushed her on the bed. I straddled her and pushed her down to her flat stomach and took the head of my cock and slowly parted the lips of her pussy. I rubbed her fast and slow with the head of my cock never entering her. After a few minutes I could barely distinguish the head of my cock from the lips of her pussy. She was so wet that’s all I could see. I entered her slowly and she moaned and gasped. By the time I was 6 inches deep her body began to pulsate and orgasm. At 9 inches deep she was shaking. By the time I was stroking her fully she was onto her next orgasm. I’d never seen anything like it before. I was so fucking gone. We fucked for another hour in every way imaginable. I finally give her my first load of the night and she gushed all over the sheets. In a moment of post-orgasm clarity I realized where we were and took her to her room. I grabbed her roomates sheets and put them in the washing machine.

She needed to lay still for a bit, so I went to cook us a well earned meal. By the time she got up we were both horny again. Before we could enjoy the meal we were enjoying each other. We went at it for a few more hours and passed out.

I woke up again around 4am. This was one of those times when my balls felt burdeonsomely heavy. I had to empty them. So I rolled over and placed the head of my cock inbetween Rachel's legs slowly teasing her bare pussy. “Mmm, not now baby," she said in a half-daze. I continued to tease her lips without entering. I leaned in and began kissing her neck. She leaned her head back toward me exposing more of her neck and I could tell she was ready. I started to enter her and could hear her expand as inch by inch opened her wider and deeper. She let out a loud moan and we continued like this for 20 minutes until she finally climaxed again. After she came I lifted her up and laid her on her back. I lifted her legs high and spread them wide apart resting the back of her knees on my biceps while holding her body up. I entered her slowly, going deep inside of her and began to build rhythm. As we established rhythm, I increased the depth of my strokes, each stroke going a half-inch deeper than the last. I stroked faster until all you could hear was her ass, soaked from her dripping pussy, hit my balls. I unloaded inside of her. And didn’t stop. I continued thrusting until I was about to cum inside of her again when I heard a knock at her bedroom door. She told me not to stop and ignore it. But the knock grew louder. Finally, she pushed me off of her, grabbed her robe and went to open her door.

Regan was obviously confused as to why her bedsheets were in the wash. She was also a little annoyed that we didn’t go out that night. I grabbed one of Rachel’s robes to join the conversation. I was better at calming people down than Rachel. But, I probably should’ve taken the time to put something else on other than her silk robe. The two were now in the hallway speaking. I could tell the conversation was improving so didn’t interject and just walked passed them to grab a water in the kitchen. As I came back Rachel said to Regan, “It is his fault.” Regan smiled. As I approached them Rachel reached down and grabbed my dick over the silk robe and said, “it is actually HIS fault” and continued to hold me by my dick. Regan looked down and I saw her pupils dilate. After a few seconds she looked backed up smiling, but still trying not to smile and said, “it always is.” Rachel then said to Regan that she thought she needed to see, “what she had to deal with.” And before Regan could respond she pushed the fabric aside. By that point I was pretty sure this wasn't actually happening. Then Rachel cupped my balls and said, “You should see his load. It’s fucking absurd.”

Regan’s phone rang. It was her boyfriend texting her saying good morning. That broke the trance we were all in. I took Rachel back to the room and never got Regan out of my mind.