This story tells you about my journey from my late teens to today, in my fifties, in my role as a submissive bisexual male.
I started studying in college to be an IT Engineer. It was eventually to be a career path for me that opened not only doors to higher qualifications, but to doors that had Masters, Mistresses, Trainers and Dominants.
My interests were still naked girls, BDSM and IT, and of course remembering my early days of reading my Dads porn mags. Of course, I had a couple of girlfriends by the time I got to college but none that ever resulted in having full blown sex. The girl who changed all this though was a blonde haired, fairly tall, slim but big breasted girl, who was interested in programming languages like me and as we loved swimming, we clicked.
As it was my first proper time with a girl, sex was great. I loved the way that she sucked cock, especially when she used to hold my cock between her boobs as she played with my cock head. Ruth however, would love to try new things, some were an instant turn on for me. She liked her nipples pulled and stretched as we fucked and also, she liked to push back and fuck hard with each thrust, to get me deeper into her pussy. And her orgasms; they were so big. Boy, she shook, scrunched up and tried to stop me fucking her every time she would cum, but I kept going driving her nuts and to multiple orgasms.
Ruth wanted to try lots of different ways and things to do with sex, but I think I came to reaching her limit, when we were with our friends for a meal one evening. We were all chatting about various things when swinging came up, and that one perhaps two of our Instructors in college were known for being in the scene.
I glanced over at Ruth to see that she was a little shocked by the idea, and she gave me a look to suggest that it was not for her. So, we continued in the conversation, acting normally, staying interested but I could see that Ruth remained guarded.
"Hands up who would try it?" Ruth suddenly said.
I acted surprised when all of the group put their hands up. I looked at Ruth and my jaw dropped open. She smiled at me and put her hand up. I quickly did the same and we all laughed and giggled.
All the time after that, we kept glancing at each other, to make sure we were still thinking the same thing. I took in everything that was said, especially who the two instructors were and what they had allegedly got up to. I was really interested but just listened intently.
When Ruth and I were alone that night, and having a slow and relaxed fuck, I asked her about the conversation in the restaurant.
"Does the thought of having a group of men and women play and lust over you turn you on?" I asked.
She looked up at me. "I have to be honest, when we were chatting in the restaurant, I got turned on." She waited as I looked down at her. "The idea didn't appeal to me to start with. I thought about you and my vibrator at the same time, but, having four men, all wanting to cum over me and trying things," she giggled, "It got me wet."
The thought of Ruth with other guys got me to thrust into her, getting as deep as I could inside her. As we fucked, she agreed that it was quite a turn on, but she didn't want all the hassle afterwards.
Then out of the blue, she asked me what would happen if one of the other guys wanted to fuck me as well. I stopped my grinding and looked at her. It never even occurred to me that would be a possibility. She shuddered as she came, then after a short while, asked, "What if they wanted me to suck their cocks?"
With my cock buried deep inside her, I looked at her, scrunching my nose, then carried on fucking thinking about what she said. I was now imagining another guys cock in her mouth and just how close it would be to me, especially if we were fucking like we were now, face to face. Would I be ok with it if he came and I got splashed with his cum?
After that night though, those depraved thought seeds were sown. Even though we had a great vanilla sex life, something was always niggling at the back of my mind about what she said and then of course, there were the other deeper more decadent interests that came with those thoughts.
Ruth even pursued the idea and I could see that something was interesting her. One night, after we used her vibrator on her before we fucked, she said.
"Suck it. I want to watch as you suck on a pretend cock."
I was quite worked up and ready for sex, so I of course did as she asked. I could see that she liked watching me sucking it, then all of a sudden, with the very lightest of touches on her pussy, she came.
So our sex life now had toys as part of our foreplay, but it was during one night that Ruth introduced me to a much larger cock looking dildo that she had recently bought. It was exactly like a cock. Flesh coloured, had a veiny shaft, hard yet bendy, but most of all, holding it next to my hard cock, it was quite a bit bigger and thicker.
Our play now involved me fucking her with it, then afterwards, I had to suck it as I fucked her. She was my first real girlfriend, and a friend who wanted to have sex with me, so of course, I would do whatever she wanted. There was one big no though. I did draw the line to me being fucked with her dildo.
She asked, "Do you want to try it?"
I had to ask if she was serious. We had toyed with the thought of anal with her, but after trying to push my cock into her, she was so tight she stopped me and we didn't want to go any further with it. I was totally ok with that, but now, as I looked at this enormous cock looking dildo and the damage it would do to me in my bum, I immediately got the cold sweats and must have looked so nervous.
"Not this one you dummy," she quickly said as I stared at the dildo then at her, somewhat relieved. She reached over for her thinner pointed and ribbed vibrator. "This one."
Well, as a testosterone driven and sex hungry young man, I was unsure but inquisitive to try, so we chose one bath night a couple of days later, to have a go.
We had both thoroughly washed everything in our own way and I thought I was ready. We had run a fairly deep bath, and after soaking for a while, I got onto all fours. Ruth soaped up my bum, then she inserted a finger in me. Wow, that was a new sensation, especially because she wiggled her finger. I didn't actually know how far or which finger she pushed into me, but I felt like I was on the verge of either blowing off or pooing. Just this feeling made me clench and squeeze her finger.
"Relax," she said giggling, "Squeezing like that, you will cut the blood off from my finger."
I too giggled, but then thank goodness, she extracted her finger. This was it. She put the head of the dildo against my bum hole. Now, my senses and feeling down there were not exactly working well, and so I was sure it felt like the bottom of a cereal bowl being pressed into me.
She started to push the soapy vibrator bit by bit into me, and I can say, I did manage to take a few millimetres, but that was it. I just couldn't relax. I was still too tight.
Ruth wanted to try again but she accepted that I didn't want to. Same as when we tried it with her, it was something that we had to work on, together. We both knew that this was not the final word on the matter.
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