My neighbor Megan and I would often get together for happy hour, and following an evening where we ended up masturbating together, we started to make both happy hour and masturbating together part of a regular routine.

Megan was forty-two years old, slender and tall standing about six-three in height. She had long, curly, reddish-brown hair, perfect handful breasts, a beautiful face, and a very tantalizing ass. Most of the time she had a full bush of pubic hair that was bright reddish orange, and was much lighter than the hair on her head. She instructed workout classes a couple nights a week and was in great shape. She was beautiful enough to command the attention of almost any guy, however, after recently ending a 16-year marriage she was very reluctant to reenter into any type of romantic relationship. Her once loving husband became addicted to cocaine and horse betting and despite many attempts to try and save her once "perfect marriage", she eventually gave up on trying to repair her husband. Suffering through years of feeling helplessly trapped in a world that was completely unstable, she now cherished the freedom and control that came with being single and had little interest in ever remarrying.

I was twenty-three at the time and having just returned from active duty, I was in pretty good shape. I was slender and athletic with cut arms and chest. I was about 5'10", and 170 pounds. I have about a seven and a half inch cock, which is probably a little above average, but I can only assume that her ex-husband had a small penis because she seemed amazed by the size of mine.

Although we were sexually attracted to each other, and we enjoyed spending time together, I knew she was somewhat conflicted about her feelings towards me. Aside from the fact that we grew up nearly two decades apart, and had significant differences in interests, there were several other factors that did not exactly make me her perfect mate. The first was my height. I was about five inches shorter than her and while she claimed that she wouldn't mind dating a shorter guy, I noticed that when we went out in public she would always wear flats when she normally would wear heals. Additionally, although she seemed impressed that I served in the military and was now putting myself through college, I don't think any woman in her forties dreams of dating a college student on a limited budget. However, the largest hindrance to the progression of our relationship was how others perceived us when we were together. Several times people had mistakenly assumed she was my mother and people would routinely act surprised to find out that we were friends instead of relatives. I could tell that she felt very uncomfortable with society's perception of a woman in her 40's dating a 23-year-old guy, and if for no other reason this prevented her from wanting to get too close to me.

She cited the emotional angst from her recent divorce as her reluctance to get involved with anyone romantically and she clearly stated that she wanted to keep our relationship very casual. This meant that while she didn't see a problem with two neighbors getting together for drinks and masturbation, she also didn't want to progress it further by having sex. I was torn on her request. I understood her feelings and shared her discomfort with people thinking she was my mother. However, I also was twenty-three years old and desperately wanted to have sex with her. I didn't entirely understand the arbitrary line she drew between being emotionally involved and having sex, but I didn't even try to argue the point. I knew I was lucky to have a gorgeous neighbor who wanted to masturbate with me, so I decided to just enjoy her company and tried to temper my desire for entering her vagina.

Soon after we started masturbating together I learned that she loved to be teased and enjoyed foreplay almost as much as having sex. She confessed that while masturbating she liked to tease herself and would experience extremely intense orgasms from prolonged periods of arousal. She craved this intensity and could have two or three additional orgasms in a row if she was sufficiently aroused for a long enough period of time. As for me, I was like most twenty-three-year-old men, where up to that point I was never patient enough to understand the sexual capabilities of my own body or how to manipulate the intensity of orgasmic release. She introduced me to new levels of ecstasy as I discovered my body's reaction to extreme sexual stimulation.

While satisfying Megan’s devotion for foreplay and our desire for drinking, we came up with what we called "bottomless happy hour". Although sometimes the drinks would indeed be unlimited, our bottomless happy hour consisted of meeting on Wednesday night at each other’s apartments to share drinks and chat while being naked from the waist down. Originally our happy hour started with us being completely naked and masturbating while we chatted over some drinks, however, we lived in an old building with radiators that only produced heat in the mid 60's and it was just slightly too cold to be naked the whole time. We found it was just more comfortable to remain partially clothed, so we left our tops on and just removed our bottoms. Additionally, the floor was too cold for walking without shoes, so even though it seemed really weird at first, we would often put our shoes back on after removing our pants and underwear. I thought I looked ridiculous being bottomless while wearing a sweatshirt, shoes, and socks, but I oddly was very aroused by seeing her in the same state. While remaining partially clothed was originally due to temperature comfort, we found it created an almost voyeur feeling of being exposed and still allowed for us to casually rub ourselves anytime during our conversations. Although it was not by design, we both encountered a very erotic sensation about sitting and talking otherwise normally while having our genitalia exposed the entire time.

It was not long after we started our routine that Megan taught me that not all orgasms are created equally. One of the first nights that we shared drinks while being bottomless, Megan forced me to chat and masturbate with her for almost two hours before letting myself cum. My reward for such torture was an orgasm that exploded all over both of our bodies with an intensity that I had never felt before. I shot cum with force and distance I did not know I could achieve. Shooting at least twelve to fifteen spurts of cum I didn't think it was even possible to produce that much. Elated by the mess that she had caused, I could tell she was close to cumming herself. As she got ready for her first orgasm she asked me to continue stroking my soft and cum covered cock in front of her. With her laying on the couch while I leaned over her body, I watched her tremble and moan to several orgasms in a row while continuing to jerk my softening cock. After about five minutes of merely rubbing myself for her entertainment I was surprised to feel my cock start to harden again in my hand. Although my penis felt a little sore as it started to get hard, it also felt good and I was proud to show her my cock was again getting hard. I continued to stroke as I showed off my hard penis but after a few more minutes it felt so good that she was no longer the only one benefiting from my show. Caught off guard by my own body, I was shocked as I started to feel the urge to cum again. Realizing that I might actually be able to cum for a second time, I sped up my pace and started jerking off with enthusiasm over her. With a look of excitement and shock on my face, I felt that familiar high sweep over my body as I looked down and watched my cock start ejaculating cum onto her hand and pussy. Clearly she saw me getting more invested into her request, but she let out a gasp of shock when she saw the cum start to dribble out of my cock. She removed her hand from her pussy for only a second to let the cum drip directly onto her clit before she frantically started to rub my cum into her pussy.

That was the first time that I realized it was possible to achieve two orgasms in a row if I didn't let myself stop. She also didn't know that was possible and was enthusiastic to see it again. With us both enjoying such explosive orgasms she suggested that we have a two hour minimum every time before letting ourselves cum. Although I greatly enjoyed it as well, I was also slightly more eager and didn't think it was possible to wait that long every time. We playfully negotiated until we agreed that the following week we would wait an hour and a half before making ourselves cum. Being that I was more than slightly chaffed from our two hour marathon masturbation session, I introduced the idea of using lube next time. Looking at my penis in its bright red state, she reluctantly agreed on the condition that I refrain from cumming "accidentally". I agreed and the following week she had a bottle of lube and a timer on her coffee table when I entered her apartment.

During the first hour and a half of our happy hour, we shared drinks and teased ourselves. We had fun as we chatted, joked, and played, all the time while being bottomless. Although we touched ourselves while talking, we generally waited until after the hour and a half to touch each other. Sometimes we would just stare at each other while edging ourselves, and at other times we would talk while casually masturbating, but we mixed up our routine regularly to keep it interesting and fun.

We were both very talkative people and while we devoted a fair amount of time to talking about sex and masturbation, we also would discuss a large variety of topics like politics, sports, and our personal lives. While I would never go completely soft while being in view of a vagina, she loved to watch how my penis would react when changing topics. She was intrigued with seeing my penis go from semi-hard and resting on the couch when talking about politics, to hard and pulsating when discussing masturbation. Although she often changed topics with the intent of watching my penis react, she would never let it rest for very long. If I went more than a couple minutes in the resting position she would do something invoke a response from my cock. Sometimes it would be as subtle as spreading her legs wider, other times it would be as obvious as pointing to her pussy, but she never let my cock rest for a prolonged period of time without doing something to make it hard. Additionally, she enjoyed figuring out what made my cock react the quickest and turned it into a game of sorts. Testing my cock's reaction to different things she managed to figured out things I didn't even know I liked.

After she had confessed that she sometimes enjoyed smelling her own panties while masturbating, she must have sensed that I thought it was a little weird and didn't quite understand why. Trying to explain, she had me close my eyes as she placed her pussy soaked fingers under my noise when my cock was semi-hard. Within seconds my cock sprung to attention and was fully hard. I guess I was always so focused on the visual attraction of a woman's vagina that I never knew that I was subconsciously aroused by a woman's scent. I was a little stunned at how quickly I became aroused, and she loved watching my reaction.

We both loved talking about masturbation, and would routinely discuss our sessions from the past week like we were talking about our work week. We would share the details of how many times that week, where we did it, the use of lubrication or toys, and what we were thinking about or what type of porn we watched. Surprisingly she had a stronger sex drive than me, and about once a week she would masturbate during her lunch hour at work. She would describe in detail about sneaking off to rub her craving pussy either in a bathroom stall, basement conference room, or in her car at a nearby park. Hearing her talk about her weekly masturbation sessions often inspired my imagination and got me masturbating in different places and ways, which would then give me a good story to share with her.

We would usually lay towels or blankets down on the living room furniture, mostly talking there, but we would often talk in the kitchen when one of us was making drinks. Sometimes while we were talking she would clean up in the kitchen or wash dishes and I would sit on a bar-stool slowly stroking myself to her magnificent ass. We would sometimes watch porn or talk while porn was playing on the TV in the background, and we had fun picking out scenes to show each other. We also liked to tease and played little games to frustrate the other. She would often take to watering her plants around the living room while reaching over me and bending over directly in front of me. She would put one leg up over the arm of the chair so I had no option but to stare at her spread and leaking pussy, and while talking she would randomly dip a finger into her pussy and taste it as if it were the most casual and normal thing in the world. In teasing her, I would pretend that I didn't know my penis was dripping precum and would be casually talking to her while a string of cum was dangling from the tip of my cock.

Soon after we started our happy hour she introduced me her basket of toys. Although I was indeed excited to watch her put them in action, I playful protested their use during the first hour and a half while citing fairness and the spirit of anticipation. She agreed, but I eventually gave in and let her insert a dildo inside herself as long as she left it idle and didn't move it. This worked really well in exciting her as she could hardly stop her hips from moving with the feeling of a cock inside her body. However I am not sure who this hurt more though as it was absolute torture to us both. Seeing her vagina filled with a rubber penis, a vagina I wanted so desperately around my cock was a painful reminder of how badly I wanted to have sex with her. Looking at her squirming as her pussy coated the toy with her thick creamy cum, I couldn't stop myself from day dreaming that it was my dick that she was coating and I could hardly carry on a conversation.

Although we would generally wait till the hour and a half was over before masturbating each other, we would often kiss and make out as the time got closer. Kissing while being bottomless for 10-15 minutes was almost torture. We would grind on each other like we were dry humping except our genitals were actually touching, and we got so frustrated and aroused that we made out like ravenous teenagers. Feeling her vagina rub on my cock while knowing that I would not get to enter her was excruciating to me and she knew it.

At times I wanted to feel the inside of her vagina so badly I could scream, but I was deadly afraid that if I pushed the issue of sex that I would only push her away, so I said nothing. However, nothing could have said more than the desperate look on my face, and she was fully aware of the pain I was enduring. To her this was pure ecstasy and she thoroughly enjoyed it. Often while making out she would be a little mean in her teasing of me that I could not have sex with her, and she loved to remind me of how badly I wanted it. As she would grind her bush and pussy into my lube covered cock she would say things like, "The inside of my pussy feels even better, just imagine what that must be like" or "You really want to fuck me don't you... I feel bad for you, you know I'm not going to let you into my pussy".

She would get me worked up to the point of complete exasperation, sometimes feeling a strong sting of anger at how cruel she could be. Although I know that she got off on pushing me to my limit, I also know that her intent was not really to be cruel. Her only real goal was to make my body produce as much cum as possible. Getting me to a near breakdown in sexual frustration just ensured that she would see a colossal manifestation of cum that would literally explode from my body. At times my testicles would ache from wanting to release so badly, and there would be a constant dribble of precum coming out from the tip of my penis. As we kissed an maid out on her couch all I could hear was the ticking of the timer on the coffee table, and nothing was sweeter than hearing the buzzer go off. Although making out dramatically escalated the intensity of our arousal, it was sometimes too hard for me to take and It was all I could do to keep myself from entering her body.

Once the allotted time was over we frantically stripped off our clothes and either pushed our chairs together or sat together on the couch. We would usually sit up and face each other with her legs over mine so we could touch and kiss. We liked to rub and feel each other’s bodies, but we also liked watching each other passionately having sex with ourselves. She loved watching me jerk off, but she also loved the feeling of holding my cock while it was exploding in her hand, so it depended on what she wanted more on that particular day.

Generally, she would start by playing with my pre-cum and then help me to apply more lubrication to my penis. However, she never needed any lubrication for herself as she produced more cum than I have ever seen from a woman and would absolutely gush a thick and creamy substance. Her cum was so thick and plentiful that her crotch would look like she was shampooing her pubic hair when she was done, and she had so much cum that if she had placed a dildo inside herself while we were talking, I would sometimes wipe it off with my hand and use her cum as lubrication for myself.

She was also someone who liked to try different things and different styles of masturbation. Sometimes she laid back with her eyes closed and would really attack herself, other times she wanted me to stroke my cock right in front of her face. She loved the feeling of holding a hard cock in her hand when she came, so I would often wait to masturbate until after her first orgasm so she could hold my hard cock with one hand and masturbate with the other. Seeing her shaking and trembling as the vibrations ran through her body while she tightly squeezed my cock was one of the most powerful and amazing things I have ever experienced.

As a younger guy, most of the time when I would cum it would already be pretty forceful and plentiful, however after being aroused for an hour and a half, it transformed into an explosion. My cum is more watery and less thick when I get extremely aroused and shoots further and with much more force. I would shoot cum with so much force that you could literally hear it splattering against her skin. She was always amazed at how much and far I would shoot, and compared it to a hose as she teased it was like taking a shower. While masturbating she would talk dirty saying "give me that shower baby, wash my dirty pussy with your cum shower".

She got such a thrill from my orgasms and intensely watched as the cum was leaving my penis. Every time she would stare and smile with a look on her face like it was the first time. In the moments just before I would cum I loved the seeing her so happy while she eagerly awaited to be covered by my orgasm. She loved the feeling of being sprayed by hot cum while she was masturbating and would usually have me cum on her just before she would orgasm again. Often she would direct me as to where she wanted me to aim, other times she would just let me cum anywhere I wanted, but generally it didn't matter where I was aiming as she would usually end up with at least some cum on every part of her body. My second orgasm was always a lot more tempered than the first, and I would only dribble a couple of thicker ropes, usually coating her hand that was finishing up on her pussy.

I still think of her while I masturbate today, and I can clearly remember the exact day that I that I had the best orgasm of my life. It is permanently ingrained in my head and the image I remember most when masturbating. Sitting up on the couch with my back against the armrest she was in front of me with one leg bent in between my hip and the backrest of the couch. Her other leg dangled off the couch with her foot on the floor. She was sitting up with one hand grabbing the couch for support and the other hand looked like a blur as she was furiously working on her pussy. I was tingling after I had just cum twice and I can unequivocally say that the first was most intense and explosive orgasm I have ever had. Watching her as she frantically rubbed her pussy to reach her third orgasm, her entire body was covered in my cum. My cum was in her hair above her ear and on her left cheekbone and eyebrow. Her left breast was completely covered while cum was dripping off her nipple. The right breast had two large drops just below her nipple. There was a stream of cum running down from her chin and neck, past her chest, down her stomach, and into her vagina. Her hand was covered in my watery cum from my first climax and there was a thick glob on the back of her hand from my second. Cum was stringing from her thumb, index, and middle fingers. Her bush was completely drenched with little orange hairs sticking through the creamy paste that covered her pussy. My clear and watery cum was mixing with her thick and creamy cum as she was absolutely attacking herself with four fingers. Her pussy made a rapid squishing sound while our cum mixed and bubbled inside of her beautiful reddish orange bush. She screamed as I watched her shake and tremble to her last orgasm.

As her entire body buckled and shook, droplets of my cum dripped off her chin and breast. Her eyes clamped shut as she hit her high and she grabbed her pussy as the intensity was overwhelming. She then opened her watering eyes and gasped for air as she looked at me. Laughing in disbelief over the intense pleasure she had just encountered she grabbed my shoulder with the hand that had just been on her pussy and was covered in cum. She teasingly pulled herself onto my lap and rubbed her body against mine soaking me in the cum that was covering her body. She then looked at me and kissed me as I got a close up view of the cum that was trapped in her eyebrow. Our embrace lasted another 10 minutes before I got a warm washcloth to give her a sponge bath.