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My Sexual Milestones: dating a man-  

SexySweet1111 34F
187 posts
5/5/2019 8:41 pm
My Sexual Milestones: dating a man-


In college I had dated a handful of boyfriends and they were all nice guys who my parents had loved. As I prepared to graduate and look for a job my current boyfriend and I tried to figure out what the future had in store for us. He was very open about wanting to get engaged and he’d go to work for his dad but I was restless and didn’t feel ready for that. My parents thought I was crazy and warned me that my boyfriend would move on if I didn’t seize this opportunity. I didn’t know what to do so I tried to put it off. My boyfriend assumed I would come around if he gave me time and agreed to take a break.

Almost immediately I met a guy who would introduce me to kinky sex. He was ten years older than I was and easily the most handsome man I had ever dated. He worked as a personal trainer and had the most exciting body I had ever seen. I still remember him wearing these tight tank tops which showed off his muscles.

Obviously, a guy like this had a reputation as a man . He didn’t seem to have many serious girlfriends but I knew a few other girls who had hooked up with him. At first I was disgusted but a lot of them had crazy stories about all the wild sex they had had that made me envious.

When he asked me out I was surprised because I wasn’t his usual type. He seemed to date the girls who struggle to be a bikini model before settling down to work at one of those breastaurants. And that was not me at all. I was raised as a Baptist and took my faith seriously. I had never hooked up and felt somewhat guilty about the sex I had had with the guys I had dated so going out with him was risky. He was also an infamous player so I agreed to go out with him knowing this was probably going to be nothing more than sex.

I was so wrong! He took me to a pool party for most of the day and we ended up back at his place where he cooked me a fancy dinner. The whole time he was the perfect gentleman and I wondered if sex was even going to happen. When it did happen it was absolutely mind blowing. After several serious boyfriends I had had sex and considered myself experienced but it was clear I was practically a virgin compared to him. We didn’t sleep at all that night and I remember seeing the sun come up while we were still doing it. We crashed for a few hours of sleep before I woke up to do my walk of shame. This is still one of my most memorable sexual experiences but years later he told me he barely remembers it.

I wanted to see him again but assumed he saw me as just a piece of fuck meat. I didn’t want to get my hopes up and didn’t reach out to him. A couple of days passed and I didn’t hear anything until we bumped into each at a fast food restaurant. He acted like we were old friends and we ended up back at his place for several intense hours in the bedroom, kitchen, living room, bathroom and the little balcony of his apartment. I had work the next day so couldn’t stay the night but we made plans to see each other again.

We got together every few days. The sex was always hot and<b> sweaty </font></b>and could take several pleasurable hours to complete. Initially much of what we did was new to me. I had heard of most of these sex acts and was curious. But there were other acts so bizarre I had never imaged people actually doing them. Gradually I tried just about everything you can do with a partner and learned to actually enjoy certain sexual activities that had been on my list of things I won’t do.

He came on very strong. He told me how amazing I was and how I was the hottest girl he knew. He made me feel like I was the only one for him. I wanted to believe this but I still saw the relationship as a short term thing before he stopped calling. I still don’t know how I kept his interest. My sexual skills were so basic in the beginning he could have done much better with any of the other girls I assumed he was probably sleeping with at the same time as me. It’s still a big mystery.

When we were together he was the most charming person you have ever met. He always knew exactly what to say to make me feel special. I was becoming emotionally attached but was so addicted to the incredible sex we were having I couldn’t walk away, something many of my friends advised me to do.

With all the late night booty calls, his requests for sex in the middle of the day when I was at work or the times I cancelled weekend plans with my friends because I was having sex with my new guy was starting to wear me out. I didn’t know if I was a girlfriend or fuckbuddy so I was leading this double life where I spent most of my free time fucking this guy while not really being able to explain to family and friends what I was doing.

I was turning down legitimate dates from very good guys because I didn’t know if my sexual situation allowed it and this forced the conversation about what kind of relationship we were having. I remember laying in bed wiping his cum off my body as he told me he had considered me his girlfriend for a long while and he was surprised I didn’t know that. I was elated!!

I now felt more comfortable investing even more effort and emotional and sexual energy in the relationship. It was nice not having to hold my emotions in check. I kept my own apartment and a roommate for the sake of my parent but practically moved into my boyfriend’s place. Being so close to each other gave us even more time for sex. We probably started averaging 3-4 times a day and some of these times were several hours long.

It seemed as if we spent all our time together having sex or coming up with nasty, kinky new ways to sexually challenge each other. We did it all. Met up with other couples, regularly went to a sex club and got off as dozens of people watched us fuck, joined several local swingers groups and even explored group sex and gangbangs. The most amazing thing about this time in my life, despite all the sex we were having we were also both chronic masturbators. Sometimes after fucking for hours I’d wake up for n the middle of the night to masturbate. I would even rub one out in the ladies room at work because I was still so turned on.

I was having the time of my life and learning new things about myself on a daily basis but gradually I started to have doubts. Sex took up all our spare time and we barely did anything else. I even started using vacation time to stay home for multi day sex sessions.

I gradually lost contact with family and friends because I was so busy having sex. I was amazed to learn a close friend had gotten married when I hadn’t even know she had a boyfriend.

I was having a lot of risky sex but didn’t consider the consequences. My boyfriend never wore a condom and many of the others I slept with through the swingers groups and other group activities went bareback too. Fortunately I never came down with anything too serious but I was having to visit my doctor more frequently than I would have liked.

All this sex left me jaded and needing even kinkier sex to get off. Even fairly kinky sex became boring to me. Eventually even sex acts that I considered gross barely amassed me and this pushed us to try even riskier sex acts.

I started to develop a sense of shame about what we were becoming as a couple but part of me felt incredibly fulfilled doing these things. I looked at our relationship and realized it was entirely sexual and it didn’t really have much substance. Even worse it didn’t seem to be developing into something new, which I viewed as an essential part of any healthy relationship. Despite my misgivings my boyfriend seemed incredibly happy with how it was going and began talking about getting engaged!

In the end I broke it off because I couldn’t see myself happy in a continuing relationship with him. The break up proved very challenging. For one thing I seemed to go through a sexual withdraw. I had had such an active sex life for a year or so and now I had nothing. For those who wonder I am still close friends with my now ex boyfriend and I hope to share the details of how I survived the break up and my continued friendship with my ex in a future blog.

Heathen_G 65M
7974 posts
5/6/2019 2:13 am

You don't want to go from continuous sex to being just friends.... Put some distance between you and him. He has other women... you will get the attention of another guy, maybe for fun, or maybe for seriousness.... either way, you don't want to mess that up trying to be just friends with your ex.


SxyLatinJazz_4u 50M
157 posts
5/6/2019 2:34 am

One can really feel in your heart if the person is really a friend or just a really good fuck with a decent personality. I used to think people were exaggerating when they say, I married my best friend. The older I get, the more I understand.

I hear ya!


SexySweet1111 34F
10 posts
8/9/2019 8:46 am

SxyLatin,

I really do agree with the idea of knowing who you were meant for and really value the idea of marrying your best friend. A lot of people don't do that and it really does effect the quality of their relationship.


SxyLatinJazz_4u 50M
157 posts
10/11/2019 7:01 pm

SexySweet,

Quantity is easier to find. Quality, not so much. Anyway, we should strike up a good conversation to see what chemistry we have and plant a seed of friendship.


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