I've been using masturbation to try and "fix" myself from my past and finally went to the next level last weekend. *some small details have been changed to protect people, just in case, but the main points of this story are all true* Sorry about the long backstory, but you need it to understand the importance of what happened.
I started masturbating at a pretty typical age I think, around 14-15, just when I was starting to get interesting in guys. Nothing too exciting or kinky, I used to borrow some of my mom's romance novels and read the dirty parts until I got aroused and then touch myself, but not until orgasm until much later.
Then a few years later in my mid-teens, my father passed away and I lost interest in sex and boys and anything like that for a while, so I fell behind from my friends in that department. Then when I was 18 I had a close call with a guy who was quite a few years older than me and I managed to get away without a bad assault but the whole experience further shied me away from anything sexual. I went off to school and managed to be the oldest virgin in my groups of friends, still falling "behind" the normal curve of my peers.
At this time I was masturbating a couple times a week, sometimes to orgasm but I was just using my fingers and never inserted anything other than that. It was fine until I reached about 21, still a virgin, not really in any hurry to change that until one night when I let my guard down around some people I trusted from University. I won't get into what happened because it is against the rules of this site, but you can safely assume that what happened would further scare me away from sexual activity. It took me a few months of "healing", both physically and mentally to be able to masturbate again. It was also around the time when I found this site and used some of the stories on here to help me get over what had happened (so thanks guys).
Another few years down the road, I was masturbating frequently again but this time I was starting to get frustrated by what had happened. My friends were all in long term relationships, starting to get engaged or married and yet I couldn't even do anything sexual with a guy without being filled with anxiety to the point of getting ill.
One night, feeling extra stressed because of other parts of my life and school, I decided to just pick up a guy and see if I could work my way through it. As you can imagine, it was a disaster but this time I decided to try a different approach. I started researching masturbation, sex and anything to do with human sexuality. I changed my major in University and decided to work with victims of sexual assault, using the techniques I was learning on myself in an effort to become "normal". I eventually got a small vibrator in order to cure my poor shell shocked vagina. I've tried a couple of times to buy a real sized one or a dildo, but I get to the store and my body sees them and goes into panic mode and I find I cannot do it.
Only two of my friends and none of my family are aware of my sexual history, they think I am just very very shy, so it is difficult to get them off my back about having a boyfriend or settling down because they don't understand the real issues.
After graduation, I decided to move back closer to my small home town, to an area filled with people that I am familiar with and where I feel safe. I have lived here for about a year now and have avoided any relationships, which once again makes me kind of the "black sheep" since most women my age are married or dating or at least have children from a previous relationship.
Then last weekend happened. I have a male friend here who I know has been interested in me since we were both teenagers. He had once attempted to initiate a sexual encounter back in high school not long after my father died but he understood when I rejected him and he remained friends. I often wondered during my whole ordeal if things would have been different had I accepted, but I guess there is no use crying over spilled milk, or so I thought.
There was a big community event over the weekend, and around 3 am when everyone was getting kicked outside, he and I ended up sitting outside together on the sidewalk. He put his arm around me and I cuddled into him, I had had more than a few drinks that night but I think it was more the fact that I trusted him which made me put my walls down. To him, he saw a potential opening that had been almost ten years in the making and I don't think he was going to let it get away lol.
He asked me if I wanted to go back to his house and I said no, he asked if he could take me home and again I said no, that I just wanted to stay like that and cuddle for awhile. So we did, and eventually I felt sober enough to drive home, so I did and to my surprise he followed me there. I told him I didn't know if I wanted to do "that" and he said it was ok, we would just see where things ended up.
Then he kissed me and I felt better than I had felt in a long time, we were kissing on the couch and he pulled down the top of my dress and unhooked my bra, started kissing my neck and my breasts, being very gentle. I tried to relax and just let go, but then his hand went down my leggings and started rubbing my vagina and I felt the familiar panic start to come in. Then he whispered that we should move to my bedroom and I panicked a little more, for whatever reason I just didn't want to bring this into my personal space. I told him no, that we would go to the guest bedroom instead. He looked a little confused, but I got off the couch and led him into the guest bedroom. I was determined that this time would be different.
He undressed me and then himself, still kissing me all over and being very soft and gentle. I tried to reciprocate, kissing him back, helping him take his clothes off, but with my limited amount of experience and the fact that I was trying not to bolt away from the room, I was not really holding up my end of the foreplay. Then he went for my vagina again, this time inserting his finger and once again my body tensed up and I felt pain. He noticed my grimace and felt me tense and asked what was wrong, I told him it was ok and to keep going. He continued to stroke me while kissing me but it was not getting any better.
Then he took my hand and pulled it down to his penis, wrapping my fingers around it. With all that had happened to me, I actually had almost no experience with what to do with it. I started stroking like I thought I was supposed to, from reading on here and watching the occasional porn video (part of my desensitization personal therapy I guess) and from the sounds he started making I decided I was doing a decent job. He had stopped fingering me at this time and was once again kissing my body, and I was completely ok with it, starting to get my brave back.
Then he started to move like he was going to enter me, and I braced myself. I can't write about what happened during that time on here because of the rules, but long story short I didn't last long before I had to get him to stop, which he promptly did, and by that time really knew that something was wrong. He asked me if I was a virgin and I started to laugh, I don't know why, the situation was not very funny at all. I had been asked about the virgin thing a few times and I knew it was a popular rumor as to why I was still single. I assured everyone who asked that I was not virgin, just not interested but I knew that some people didn't believe me.
At that time we were lying side by side (I had been on the bottom during the unmentionable part) and I could just feel the words bubbling out of me. I climbed up on top of him and straddled his legs, mad at myself for how lousy the whole time was for him. I started to spill everything that had happened to me and while I was talking I started playing with his penis again. I think it was part needing to get it off my chest and part thinking to myself "I will not be scared of you anymore!"
As I was telling him my story, I could see how much it surprised him, he asked questions, I answered, I continued to stroke him but I could feel that he was slowly losing his erection, probably from shock at my super secret past. I asked him if he remembered that time in high school and he said he did, I told him that I had often thought about how things might have been different if I hadn't rejected him. I closed my eyes then and knew it that I needed to see if I could do it, I had never given a blowjob or had a penis anywhere near my mouth before but I also felt like I kinda owed it to him.
I scooted down and wedged myself on his left side, his arm went around me in kind of a cuddle, I think he thought that I just wanted to be comforted for awhile. I continued to stroke his penis and then surprised the crap out of him when I lifted my head up and took it into my mouth. I tried to breathe through my nose and closed my eyes again, started trying to do the things I have heard/seen but never done. I heard him suck in some air and his hand started stroking my back and my butt, very lovingly, not making any move towards my vagina at all and I was super grateful for that.
It wasn't long before I had to pull my head up to get a deep breath and I looked at him, stroking it again with my right hand to try and keep the erection alive. He made a comment about my skill and I laughed again and told him that I had never done this before. I put him in my mouth again, feeling a little bit more comfortable to take him deeper and he started whispering encouragement and giving me directions occasionally (watch your teeth, use your tongue, things like that). Whenever I needed to come up for air I would continue to masturbate him, determined that I would make him come.
After probably close to twenty minutes, he gently pulled my head back and removed my hand, he gathered me under his left arm and cuddled me, with my head on his chest, still stroking my back or my hair softly and started masturbating himself. I just watched him and then about three minutes later he finally came, spurting a couple times into the air and it landed on his chest and a bit on my face and hair. I didn't really care, I was the most comfortable I had ever felt in that kind of a situation and we just laid there for a few minutes not saying anything.
The sun was up by this time, and I told him he should probably leave, he got dressed really quietly and I just laid there, wrapped up in the blanket and watched him. Just before he left he told me to make sure I texted him later because he really wanted to talk with me about it and I just nodded.
I didn't end up texting him, and after a while I started to panic. I spilled all the beans about me to him, what if he tells somebody? What if he tells my family? (he is close with all my brothers). I called both the friends that know about my situation and they said that he won't. I am not sure about what to do next though, my friends say that I have potentially found a "lover" that can help me get through the healing process but I am not sure how ready I am for all that yet. Right now I am at more of a "let me touch you but I don't think you can touch me" kind of a place, and is that really fair to him? Do I really want to do that to a friend? Are we still going to be able to be friends after this? I don't know.