D (32M) and I (40F) have been dating for almost 10 months now (*D: 10 months tomorrow!*), so this was our first Valentine’s day together. We were both very excited! We had some weed that we had decided to save for the occasion. We had bought each other presents, and went to a Japanese restaurant near my place. We had a very nice dinner but were quick to leave the table once we were finished eating, because the fun was going to happen back home.
About a week ago, D had sent me a message, role-playing a patient making a doctor’s appointment for a checkup and a prostate exam (*D: our first REAL role-play*). So we had made an appointment for after-hours on the 14th, at exactly 10pm.
Back home, the evening started with opening a bottle of wine, smoking weed, and D doing his nails. He likes wearing nail polish when we’re together, and he looks really cute that way. We opened our presents. D got me an amazing vibrator, something I had never seen before! It feels so good. And I got D a prostate massager.
All this took us to 9:50, at which point D excused himself to the bathroom, and I started preparing the doctor’s office – took out a pair of latex gloves (*D: bought especially for the occasion*), a jar of coconut oil, his brand new massager, and, on the side, my harness with a 7″ strap-on dildo (*D: Which we’ve used on MANY previous occasions, and I love that thing…*).
My patient showed up at 10, wearing super cute panties (the ones I’m wearing in the last picture of me we posted), and, I think, feeling a bit nervous (*D: Yup.*), like me, because it was the first time we would be role-playing for more than a few minutes.
I had him lie down on the bed/exam table, on his stomach, and proceeded to palpate the small of his back and his upper thigh, asking if he felt any pain or discomfort. Then I told him I had to pull his panties (cute panties, I told him) down a little. I gently spread his butt cheeks to reveal his tiny hole, and kept palpating all around, still asking medical-ish questions. After a short while I told him that I had to check inside his ass, and pulled his panties all the way down. I said it wouldn’t hurt, and that I first had to apply a lubricating lotion. When this was done, I gently pushed a finger in his ass, and started probing, rubbing, and massaging his ass (oh the feeling of the latex when I touch his butthole…!). Then I gently finger-fucked him, at which point he asked if this was all part of the exam. I told him yes, reassured him that this was a thorough procedure but that it was all necessary.
I continued fingering his ass for a while. By this time he was on his back, and we moved on to using the massager. Apparently it feels really good (*D: indeed it does! I was squirming!*)! It was awesome to see him contract his butt and thighs, and wriggle to pull the plug deeper in.
The doctor (me, if you’re still following) suddenly took the patient’s dick in his mouth (*D: she was role-playing a MALE doctor, if that wasn’t clear…*) and sucked it. D asked me if it was all normal, and I told him that he seemed to enjoy the procedure a little too much… he replied in a panting voice that he wasn’t a slut. From then, I started to call him a slut, telling him I knew from the beginning he came to see me because he wanted his ass fucked. I made him admit it and beg for more (*D: Which I quite earnestly did*).
He complied, so I took the harness and told him he would get what he wanted, asked him to lie on his side, and slid the dildo in his ass. I fucked him so hard, it was amazing!
We spooned like that for a while, me calling him slut, and bitch, and whore, telling him that from now on he would be the doctor’s dirty little slut, that he would make sure his ass will be available at any time for the doctor, and that he would get fucked every day (*D: And pulling my hair – hard. *).
Then I turned him on his stomach, put the dildo in his ass and fucked him really hard. He was moaning and groaning, I loved it. I was close to cumming but I didn’t. I would have loved to tell him that the doctor was cumming in his ass!
I think at this point he asked for a break. He went to the bathroom, and when he came back I fucked him again, this time on top of him. It’s not the easiest of positions for me yet, but we still managed to enjoy ourselves very much. I asked him if he wanted the doctor to make him cum (“Yes, doctor! Please, doctor!), and told him to ride my cock.
I rolled on my back, he straddled me and quickly sat on the dildo. I love that view, him on top of me, his erect cock on my stomach, and me thrusting the dildo deep in his ass. I fucked him for 5 or 10 minutes (*D: I’m not even sure it was 5 – I was ready to CUM! We’d been at it for quite a while*), he was jerking off, and I told him to cover me with his cum. I was still telling him what a slut he was for liking it so much, that he was about to cum with a big dick in his ass… and he got off like that, riding me, spraying a huge load of creamy cum on my belly and tits (*D: right up to the collarbone…*). When he rolled on the bed, I told him to spread his cum on me. It was amazing for both of us! Fingering him with the gloves made me feel very dirty (which I love), and I got to fuck him really good. I can’t have enough of hearing him moan and breathe deeply… (*D: And I’ll be happy to oblige anytime…*)
After this, we started to work on my orgasm. I came really hard from everything he let me do to him.
What a night!
Source: reddit.com/r/gonewildstories/comments/5ua0cb/how_we_enjoyed_our_valentines_night_with_notes_by