01 Surrendering to Pleasure

This is a personal fantasy of mine and everyone in this story is in their 30s

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We agreed (read: she told me) to meet for drinks ahead of time and that I'd wear something sexy under my work clothes. I had picked out a cute thong, a fairly femme lace jock and a pair of see through mesh briefs that I thought would all be exciting to be seen in (and hopefully to see) and packed them in my bag to change into before I left for drinks.

The day ended up being chaotic which was probably for the best as we had been talking a lot about the activities we planned the days leading up to this night and I had been very distracted at work, worked up and the constant excitement was causing my dick to drip precum unexpectedly throughout the day, causing me to be on high alert that I would walk into a meeting or talk to someone on my team with an obvious fresh cum stain on the front of my pants.

When it was finally time to go to dinner I was originally going to start the night wearing the lace jock as I thought that would get the biggest reaction but then realized if I did that, everything else would probably feel less exciting. Instead I slipped out of pants and underwear in the bathroom and slipped on the very small thong I had brought, feeling it rest teasingly against my hole and holding my dick and balls comfortably in place.

I hadn't worn a thong under my normal clothes in what felt like years and the sensation of my bare cheeks rubbing against the rough fabric of my chinos was alarmingly tantalizing and I was worried I'd be noticeably hard or, worse yet, dripping through my pants before I got to the restaurant.

When I got there I secured us some seats at the end of the bar and waited a few minutes for her to arrive. When she showed up my heart fluttered a bit with nervousness and my brain was already turning to mush anxious for the night. She wore a long coat and underneath had a skirt with a slit up her leg that exposed her thigh while she sat next to me; her tight pantyhose hugging her thighs and gliding luxuriously under my hands as we talked and had a couple drinks.

We had agreed on just two drinks and then we'd leave for her apartment so as we finished our drinks and I paid the check I called a car for us and my excitement continued to grow. I had promised to make her bed in just my underwear when we got to her house and was excited to be exposed in front of her and the large windows next to her bed. In the car we sat close with her leg over mine and her hand slowly tracing light circles up the inside of my thigh, timing it so for the last minute or so she was teasing my dick through my pants. I could feel myself stiffening and straining against the front of the thing which in turn was pulling the back of the thong tighter and deeper into my crack and my hole.

Finally we were at her house, both of us turned on and excited for the night to come. We started with me stripping down in front of her and letting her see my body in the thong I wore. Then, as instructed ahead of time I got to work making her bed, taking care to do a good job and not rush it. Luxuriating in the sense that I was being useful, being objectified and was incredibly exposed. Once the bed was made she instructed me to fetch and tray and bring it to the bed to set down beside the pet blanket that covered most of the bed and as I grabbed it I discovered an assortment of curated sexual gear including a strapon, lube, a vibrator, a tongue attachment for a wand, baby wipes and a lube shooter. Needless to say it was a delightful bit of foreshadowing.

Afterwards she excused herself to clean up a bit and told me to change into my other underwear. I was excited to oblige and quickly scurried across the room to my bag to pull out the lace jock And get it in place with the thin, delicate straps perfectly framing my ass under the lace band. I ran back and waited for her to come to the bed with eager anticipation. When she did she could only see the front of the jock which just looked like lacey panties and she immediately started to feel me up, rolling me over on the bed like I was a pet or a doll to see the back and eagerly grabbed at my ass when she saw the open back to them.

She grabbed me and felt up my body and my ass like I was her property to explore and enjoy how she wanted and we made out while I grabbed at her in return. We made out for a bit while she straddled me, grabbing at each other as I worked to get her clothes off of her. There was a brief pause and she got up to grab some water and her weed pen and while I sat unsure of what to do with myself she suggested that, in the interest of not taking another break I should go to the bathroom and clean myself out to prepare. It was nerve wracking and exciting to be bent over on the floor of her bathroom giving myself an enema and felt incredibly vulnerable knowing I was doing this seemingly dirty thing for the sole purpose of letting the beautiful woman in the next room fuck me mercilessly with her huge strapon.

When I finished up, cleaned myself up and came back she was seated with her back propped up against the back of the bed wearing a long soft silk robe and indicated I was meant to sit between her legs with my back toward her. She took that opportunity to reach her long legs around me interlock them with mine making it impossible to move and get away while her hands reached in front of me and slowly, teasingly stroked my dick while I slowly realized the firm pressure I felt against my back was the head of the large girthly dildo she had strapped securely to her hips. She was kissing my neck while I panted and shifted around trying trying to stimulate myself against her hand to no avail. I guess it was obvious to her (or else she was just as excited as I was) that I wanted to be fucked so badly I could barely stand it and asked me what I wanted. I was embarrassed to say it but I couldn't hold back and admitted I wanted her to fuck me with that hard shaft she had been pressing into my back and she leaned in and asked if I wanted to be on my back to start while making it clear I was expected to give clear, honest feedback of what I wanted. What I wanted right then was to be bent over like a slut in front of her while she wrecked my hole so I told her (omitting some of those details) that I really wanted to start bent over.

When she let me up I climbed forward on all fours and instinctively pressed my face and chest into her mattress with my back arched, my legs spread and my ass hungrily in the air. Her comments about how attractive I looked in that position, which also dripped with commentary on how quickly and naturally I assumed the position, had my heart fluttering. I had wanted to be fucked for so long and I knew I was moments away from this large cock (that I wasn't sure I'd even be able to fit inside of me) stretching me open and pushing its way deep inside of me in ways that were going to leave me helpless to resist.

Rather than just jump straight into pushing it inside me she started by grabbing and admiring my ass and placing sweet kisses on my cheeks before she, very unexpectedly, dragged her soft warm tongue against my hole. I let out an audible moan in response and arched my back a little further to show my enjoyment. I could feel her tongue gently gliding around the outside of my tight hole and then felt it every so slightly slip past the outermost surface, making me suddenly all too aware of how tense I was and forcing me to consciously relax myself so she wouldn't feel any resistance. While I was nervous in general and this was a vulnerable space for me to be in, having felt for so long like no woman actually wanted to do these things so much as they would put up with it if it was something I asked for, I was confident when she stopped that it wasn't because she wasn't enjoying it but rather that she was too excited by my moaning to wait any longer.

She pulled back and spread some lube over my ass with her fingers which she very quickly escalated from a surface task to an interior task, not hesitating to slide her digit inside of me and feel her way around. Soon she was fucking me with her finger and I was moaning, slightly pushing my hips back and enjoying the sensation of surrendering to her touch, knowing that for the rest of the night I was going to be doing everything I could to accommodate any desire wanted to explore with my body... luxuriating in the feeling that she wanted me and wanted my body and found my body to be a source of pleasure in a way that had more to do with what she could do to me and what I wanted to let her have access to rather than what I could do to her (although she was certainly giving me access to a set of desires that were as elusive for her as this was for me). It was the feeling I had been trying to capture for some time and I would learn soon that to be feeling that so early on was a sign that the rest of the night would lead me to spaces of pure ecstasy and wanton lustful disregard for any sense of what was proper or respectable.

...... to be continued with Part 2 soon