For those of you that have managed to stay with me through my stories from my younger years, will have realised that my relationship with Elaine was not that sexual. I was in sexual situations, but it was all for the benefit of others, but that changed one November evening.
I had been home for a weekend, and Elaine had found out from Auntie Linda. I was invited to Elaine's house, and expected the usual situation. I was excited, trips to Elaine were always enlightening and I loved them.
I was surprised to get invited in by Elaine herself, given a drink, and invited straight into her sitting room. The house appeared empty, and I sat down as instructed.
Elaine sat near me, and explained,
'James, we have been friends for almost 2 years now, and I wanted to know that I have really enjoyed your support for my fun evenings and naughty friends. At our last meeting, I will confess that I started to have feelings for you. It happens occasionally, I try to keep my private life and party life separate but you are one that has bridged the gap. So, tonight, if you are willing, then I want you all to myself'
I was a bit quiet for a minute. Elaine was mid 40s, and a lady that I would have described as handsome more than classically sexy. Horsey, does that work for you? Well spoken, clearly affluent, dressed as one of the country set, and hugely practical when it came to naked men!
But, I was also curious, because when I thought back, I had never seen her body in anything less than a basque, and that had been cleverly concealing too.
'James, you are thinking too much, this is not about a relationship. What I am offering is sexual release for us both and, obviously, under my terms. I like my men to be obedient and under control, so if you agree then we will have an evening that you will remember for the rest of your life'
What could I say, I was nervous but also curious. It had to be done.
Elaine sat back and we chatted for a while, but I could feel my cock stiffening, and I realised that I had felt this feeling before. Elaine smiled,
'Sorry James, I spiked your drink, your cock will be hard for hours. No harm, but I love to experiment with guys. Shall we start? I want you naked and in the next room. I have a frame set up and we will begin with you strapped flat for me to tease and excite you'
I was well used to her frame, and it was almost reassuring to be tied in to it. I could not move much, but I liked that my hard cock was exposed and Elaine just sat there, talking to me and stroking it.
'You good boy, always so hard for me, and such heavy balls. Now, I know that you love being sounded, so why don't we start there'
Elaine produced a selection of steel rods, she squirted some lube on my cock, and picked a thick ribbed rod. She twirled it in her hands, looked at it from every angle and told me that she hoped I could take it.
Oh, it felt so weird, stretching my poor urethra, and those ribs just tickled and teased. Elaine tapped the end, gently, and bump by bump, the rod went deeper and deeper. This was deeper than I had ever taken before, and then Elaine told me that I deserved this. She held the end, twisted the rod and started to bounce her finger against the side. Oh, that felt strange, and oh so good. Elaine was smiling,
'You want to cum don't you, that is such a weird feeling for a guy, look into my eyes and give in to it, think about cumming, go on, pump it out for me'
That was it, I could not resist and Elaine was smiling as my first spurt built up. She slowly pulled out the sounding rod, and pulled it loose just as I started to pump. With a small laugh, she sat back and watched as my cum oozed out of my cock.
'Good boy, you almost had an orgasm, what a shame I ruined it. Your cock must feel so messed up, does it hurt? No? Oh good, some cum escaped, here I will just lick it off. Mmmm, young cum is so nutritious. Now, I bet that you really need to cum now. Do you want me to wank you?'
I agreed, and immediately regretted it as she grabbed aggressively and started to harshly stroke me off.
'Oh James, my young wanker, let Elaine drain those balls. Oh look, so much precum is cumming out, those balls must be getting so empty. You are still so hard, perfect. I won't lie, this is going to hurt a bit, please moan or cry if you need to.'
Elaine got on the frame, and lowered her shaved pussy onto my tender and sore cock. A sharp intake of breath accompanied her taking me deep into her. My cock was on fire, and as she started to move up and down slowly, I could not help but moan. Elaine licked her lips,
'Oh yes my fine young man, your pain is my pleasure, are your eyes watering? You do know how to make a lady excited'
After ages but could have only been 15 minutes, Elaine gave a shudder and thanked me for her orgasm. She smiled and said that she was a greedy girl, and a long while later, she had another. I was getting a bit out of it by then, I could barely feel my cock at that point.
Elaine got off me and looked at my cock.
'I think it is empty, shall we check?'
She reached across and I started to say 'no, please no' as her electro stim machine came into view.
'Relax James, this will make you cum for sure, let's see how much cum you have left'
Elaine was clearly enjoying it as she attached the electrodes and started it up. It felt warm, and as it cycled, it started to take away the pain, and I felt that wonderful feeling of an orgasm building. Oh my balls ached, but I knew what would happen. Elaine was encouraging me,
'Oh James, go on, enjoy that feeling, let it build up, hold back for me, save it as long as you can. Is it too much? Then cum, cum hard for me'
So I did cum, except I didn't. I pumped and pumped but nothing came out, but the pain was intense. I was crying out and Elaine was smiling,
'Oh James, that is wonderful, you have managed a dry orgasm. I so hoped that you could do it for me. You have really made this night special for me, we must do this again'
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