For many years I used to babysit several times a week for three kids. I was 15 when I started and Tyler was only six at the time and had a brother three and a sister who was not yet two. They lived next door to me and I enjoyed doing it and got along very well with all of them.
I babysat for them off and on for almost nine years and think Tyler was about 15 when I couldn't do it anymore because of my job. His mother still didn't trust him to watch the younger kids so they hired another babysitter. I had my own apartment even though it was only a few blocks away. I saw him naked fairly often over those years and many times saw him masturbating as he got older. He often tried to peek in at me if I were showering or changing clothes and I caught him several times. I still saw all the kids often mainly because my parents still live next door to them. When Tyler was 18 he came to my apartment one evening and tearfully admitted to me that he was gay. No one else knew and I was completely shocked when he told me. I did promise not to tell anyone but did encourage him to tell his parents and siblings. It took a few months but he finally did tell them and as much as his father was disappointed and mad about it, he accepted it after a while. I'm about 11 years older than Tyler but for some reason everytime he had a problem or was troubled with anything he always confided in me more so than his parents or siblings. During that first year I knew he was gay, I met four of his boyfriends/partners, but he still seemed to have problems having a long relationship with any of them.
He would call me several times a week and asked to stop over at my apartment once or twice a week. At times he was up-beat but other times he was miserable and pathetic. He talked about his relationships and the troubles he had with several of his sexual experiences. He was too open sometimes and told me things I wasn't prepared to hear about. Mostly about how some of the guys he had sex with that were actually abusing him. It was gross when he told me of how some sex acts were done to him. Things I really didn't want to know about but was still sympathetic to the way some of them treated him. He is not very muscular and I could see how some of those larger men could control him. He also admitted meeting some men over the internet which I think is dangerous for him. I also confided in him about some of my relationships and the men I dated, some good, some bad, but never serious enough for me to get married. As it turned out the two of us were not very successful with our sex lives.
Last year (I think in February) he was at my apartment one night. I had just stopped dating a guy that I found out was married. Tyler was beaten up the month before by a guy he dated a few times and his one eye was still blood shot. After talking about how pathetic our sex lives were we both started laughing about it. The conversation turned to when he was younger and I babysat for him and his siblings. He remembered calling me Headur all the time instead of Heather and we talked about all the funny things his brother and sister used to do. Then the subject came up about how he used to peek in at me whenever he could and he confessed to seeing me naked many times. I also told him how often I had seen him naked and how I would catch him masturbating. He said he knew he was gay when he was a young teenager but still liked to see me naked. Then the conversation got more personal and he started questioning me about my sexual needs and sexual situations with my boyfriends. By this time everything seemed out in the open and I did tell him of some of my best and worst relationships. I went as far as to admit to maturbation and even told him of some of the embarrassing things I did or had done with some of my boyfriends over the years. We were totally at ease talking about those things and it seemed to make us both feel better. I even showed him my two dildos and my vibrator which he was amused that I would have those types of things. I told him things I would never confess to anyone and he did the same. Some of the things we told each other were about the most humilating times in our lives. Some very traumatic but others that were happy and fulfilling. We basically bared our souls to each other.
The following week he came over again and I made us something to eat. As we sat there eating, we picked up right where we left off the week before and started telling each other more experiences. We went into the living room and he began telling me of one guy he really liked but had broken up with him. He started telling me how they masturbated each other and I noticed he had an erection. I normally would have never said anything to him but did. It didn't embarrass him but he did put his hands over his crotch and started to laugh. I laughed also and then out of the blue he asked if it was ok for him to jerk off. I just looked at him for a moment and said 'here'?, 'now'?. He mentioned how I had told him how many times I had already seen him masturbating and without thinking about it told him to go ahead if he wanted to. With that he pulled down his pants and underware and leaned back on the chair and masturbated in front of me. I hadn't seen his penis in many years but saw it didn't grow very much. Of all the boyfriends I ever had sex with, they all had a larger penis than Tyler did. Its probably only about 5' when he has an erection and only maybe 2' when soft. I do admit at the time to being slightly aroused but it didn't effect me much, I think because I knew he was gay. After he ejaculated he actually apoligized about it but I told him I didn't mind him doing it. It must have stimulated me more than I thought at the time because after he left I masturbated myself.
The following week he never called me until Friday and came over that evening bringing Chinese food. I am not sure how the conversation went at first but remember him asking me if I was offended by him jerking off in front of me. I really wasn't and told him so and he went on about his penis size to the point where we started laughing again. With no inhibition and without even thinking about it I told him I masturbated after he left. The subject of our conversation got confusing after that and somehow the topic of masturbation went into detail and we began explaining to each other how we liked to do it. If anyone heard how we spoke to each other they would thing we were insane. We were roaring laughing at times mentioning how he was gay and I was straight yet so open with each other. I think it was Tyler who brought up the subject of masturbating together. At first it was just fantasy but it began to be a serious possibility. It started when he started telling me how many times he saw me naked and how often I saw him the same way. By the time we got into the living room it became more arousing to me even though he is gay. I kept saying it was a crazy thing to do and how neither of us had sexual need for each other. Thats when Tyler pointed out that neither of us had a boyfriend at the time. Then mentioned how ironic it is that we both crave men, which only caused more laughter. It was he who first started taking off his clothes and at the same time encouraging me to also undress and masturbate. What came over me, I don't know. There I was facing a gay man undressing in front of him and finding myself aroused by it. He was naked first and sat back on the chair. As soon as I had everything off I sat back on the sofa directly across from him and began fingering myself as I watched him jerk off. Amazingly as I saw him cum I think I orgasmed two times. When the two of us were finished we just stayed there naked looking at and talking to each other and again laughing about it.
From that night on it has developed into a once a week arrangement. It happened slowly but over a period of months we began masturbating each other. His penis isn't very large but when he is erect it is hard as a rock and at times the amount of cum he produces is incredable. The very first time I masturbated him he closed his eyes and at one point said the name Gary. That was the guy he liked that dumped him the year before but I only smiled when he said that. It has gotten sort of extreme after awhile because now we shave each others pubic hair and I get him to use my dildos and vibrator to satisfy me. Some nights I orgasm so many times I lose count or can't remember. I use the vibrator on him most of the time now and he enjoys it inserted in his rectum as I masturbate him. He mostly has his eyes closed and I often ask him what he thinks about but he never tells me. I started dating a guy a few months ago but have gotten so much pleasure with Tyler I continue to have him here once every week. My boyfriend has met Tyler a few times, knows he is gay, but unaware of what we have been doing over the last year. He obviously has no idea Tyler is the one who shaves my pubic hair all the time. I like masturbating Tyler but am still not sure if he likes doing it to me. I am sexually attracted to men but still know Tyler is attracted to men also. I suspect he only satisfies me in order to have me jerk him off. He always seems to be in another world when I play with him and sometimes keeps his eyes shut the entire time. Even though I am naked when I masturbate him he never seems interested in looking at my body often. It is completely different when I am with my boyfriend as he likes looking at me when I am naked. I thought for a short time that Tyler might be bisexual but do realize he is truly gay. I think he just feels comfortable with me and know he really likes me. He is also in a relationship with a guy right now. I never met him but Tyler told me he is an older man around 50 years old that treats him well.
As unorthodox as my relationship with Tyler is I look forward to it every week. Sometimes I cook or we just order take out then please each other. We never do anything more than masturbation and I know he wouldn't want to do more anyhow. I suggested oral sex one time months ago but it completely turned him off, so I never mentioned it again. He always seems content while I am playing with him and masturbating him but I know he doesn't like me to talk when I am jerking him off. I'd like to know what he is thinking about and suspect it is about a man doing it to him. There are times he seems completely uninterested in me but is always able to have me orgasm several times. I just hope he doesn't think of masturbating me as a chore or a payback for satisfying him. He rarely touches my breasts even though I have asked him to, so I have to fondle myself sometimes as he either fingers me or uses the dildo and vibrator. I question myself sometimes as to how I could possibly get into such a relationship with a gay man. On the other hand I really like Tyler and he has become a close friend. I can tell him anything and am confident he would never tell anyone what we do, not just for his sake but mine also. All my family and friends know that Tyler and I are close, but because he is gay, would never dream of how intimate we have become.