I would have been 25 at the time, quite skinny, clean shaven with long curly hair. We met on Adult Friend Finder – is that still a thing? – and I had a very bi profile looking for MF couples I could be pals with. There was some success on that front but those are stories for another day.
She was a lot taller, a little older and definitely more experienced than me. She started me off by reading her erotica – there was one particularly vivid one about facesitting and pussy worship that I still think about sometimes. I mean, I think about everything about her a lot but that one bubbles up from time to time and surprises me.
She encouraged me to write erotica of my own and to send it to her so she could get a sense of my fantasies. I had never done this before so had to think long and hard about what I felt was hot and what the gist of my daydreams were. She gave a pretty strict deadline for them and became angry when they came a little later than set – I didn’t realise that was all part of the game.
But she liked the stories and she sent me a reward – a little butt plug for me to wear and model for her. Now if I didn’t like showing off I wouldn’t be on here and I certainly wouldn’t be on Adult Friend Finder in 2010. She wanted to see me put it in and as many cumshots as I could manage while lying on my side, wriggling it in and out with my kegels to fuck myself. We talked about what kind of harness and dildo I’d like and my heart sang when I picked out the sexiest crotchless pleather harness and big purple dong I could afford.
Then she brought up something quite plainly – how did I feel about dressing up in women’s clothing? Now I played it cool but at this point all of my experiences with men had me sissied up (more stories for another time) and while I wasn’t sure it was my favourite thing it was certainly very exciting. I marched down to Ann Summers and bought myself some red stockings, panties and a bra and was modelling them for her within the hour. It was time to meet.
I met her at the train station with my girly clothes on underneath my work clothes – I’d been wearing them all day and feeling the difficulty of the constant adjusting, fixing and digging that doesn’t really get spoken about in breathless stories like these. I had our strap-on and buttplug in my backpack and my legs were shivering with nervousness but we stopped at the station bar, had a drink and a breather, and we talked about how we wanted the evening to go. It’s a little painful to remember and describe how gorgeous she looked – tall and confident and dignified with an immaculate braided weave. She had come from work too – she was a higher-up at an advertising firm and was wearing a silver dress jacket with long lapels. She told me, quite conversationally, that the previous night she had been fucked raw by a 6’5 muscled hunk and was looking forward to the opposite of that. I was a little hurt inside by this, again not quite realising that it was once again all part of the game. It wasn’t all about me getting fucked up the ass by a woman, she had her own indulgences to bring to the table. I had a lot to learn!
It was a cold winter evening and she’d left the heating in her house on all day to prepare. She gave me a tiny pink silk dressing gown and sent me upstairs to shower and prepare. When I came out of the shower, the gown making me feel more naked than actually being naked, she had done some preparation of her own – she was wearing an imposing netted body stocking that I’ve fallen for on her AFF profile. It covered her belly and run up between her full, brown breasts. She told me to dress in my girly clothes and get on the bed. I did so without a word, my throat feeling dry. She walked round the bed, took a handful of my hair at my scalp and pushed my face down into her pillow and asked me to describe the smell. I can remember that scent well – her hair, cigarettes, a fading sense of sex. She lazily circled a pointed finger across my butt cheeks and around my balls peeking out from my panties. She asked me to go over to the mirror and model for her.
I watched myself approach the mirror on the far side of the room and got a thrill at seeing myself this way – you didn’t need to look at my erection straining against the elastic of the panties to see how *up for it* I was. She called out poses for me to take – squeeze cheeks, bend over, suck on a finger, and I was in the full lift of being objectified, of being desired. She tossed me my buttplug and rolled a bottle of lube over to me and told me to give her a show. I lay on the floor facing her and she grinned wickedly as I eased the plug in. It was just a little thing, an appetiser, but it felt amazing going in and when I kegeled it up and down it was like a kiss of a fuck. She purred and told me to crawl over to the bed. Butt plugged, pantied and pointing upwards, I padded over.
She had the blankets pulled over her. As I approached the bed, my chin level with the mattress, she gently pulled them back to reveal her purple cock standing upright and hungry. She gave me a look and I gave her a look as she sat up and opened her legs. For the first time I saw her immaculate cunt, framed by the crotchless harness, a vision of paradise with a thick and delicious smell. She didn’t need to say it but I waited for her to do so: ‘Eat me and suck me.’
So I ran my tongue over her salivating pussy then sat up to lick right up her cock, brought my lips round its head and sucked it up and down before returning to her wonderful slit. Licking and sucking, lapping and deepthroat – why can’t it always be like this? She was stroking my head and cooing in encouragement. I’d be perfectly happy with being frozen in time at that moment forever but something even better was about to happen. ‘Get up here and on all fours,’ she said and when I complied she leaned over me and ran her fingers over my butt, my stockings and snapped my bra strap experimentally. ‘You look so pretty,’ she said as she gingerly rolled my panties down over my thighs, removed my plug, set it down on a towel and then slipped a finger into my . ‘Does that feel good, my pretty kitten?’ I moaned a low yes and a thank you and she stroked my back while wriggling her finger back and forth over my spot. ‘Do you want me to go to two fingers, kitten?’ she said and didn’t give me a whole lot of time to respond before landing a very solid and hard spank on my ass. I stiffened and lurched and I felt a hot and telling blush rip across my face. I yelled in surprise and something that definitely wasn’t pain. ‘I’m going straight to three,’ she said, following up with a few lesser spanks for good measure. I felt her cock drape heavily against the back of my thighs, still wet from my mouth.
She took her cock in her hand and ran lube up and down its length. It was a cock made for fucking boys – a thick head, long thin shaft with a tapered swell at the base. I’d been practicing with it at home and it was difficult to take. I was a little apprehensive about getting around that big thick head. She might have been thinking the same thing. ‘I’m going to put all of my fingers in your pretty pink pussy, are you ready?’ I gulped a little yes and she carefully tented her fingers and opened me up like a love letter. Presently she said, ‘Do you want to take my cock now?’
I wasn’t sure if I was but my heart spoke for me. While her fingers slid in and out she responded, ‘Tell me how much you want it?’ You can be sure I begged and pleaded for her cock, ached to be fucked, and she listened patiently, her fingers just about fucking them all by themselves while she cocked her head and judged whether I had made a good enough case. Finally she made her decision: ‘Put your forehead on the mattress and both hands flat either side of your head.’
The pressure came. Pressing on hard against my hole. She circled that thick ahead around and around. I was of course helpless. I pushed back eagerly. ‘Easy there. We’re going to fuck you even if it takes all night,’ she said as she gained a little purchase at the very lip of my hole, then pulled back, then pushed in for a little more, then out, and then, all at once…
Good redditors, I know exactly the proudest moment in my entire life and it was when the head all of a sudden popped into my hole and I slid down her cock. In the sheer naughty ecstasy of it. I felt loved and sexy and held and slutty and wanted.
She’d prepped me like a master – there was no pain, just the wonderful feeling of fullness and that just-about-to-sneeze feeling in my prostate. And all this before she even started thrusting. She held onto my bra strap and pressed her powerful hips up against my flushed butt cheeks again and again. I felt the flared base of her cock on her advance and felt my sphincter squeeze down on the narrower shaft, so much like a heart beat.
She told me that I belonged to her now, that she was making me hers, that she’d worked hard and had been patient and now she was getting what she wanted. Honestly, even if I weren’t being ploughed by an expert I felt like I could cum just at hearing those words. She told me to repeat them, to agree with them all and then of course she fucked me harder to make it extra difficult but I was determined. I was bent over on my hands and knees in pink bra and stockings with my panties round my knees and she had definitely made me hers.
Presently she turned me around like I was on a spit and laid me on my back so I could gaze longingly up at her as she fucked me. Can you long for someone who already has their cock buried in your ass? You can long for the moment to last, for you both to never get tired or sore, for there to be more time with her, so much more.
She had my cock firm in a slippery hand and she told me not to cum until she allowed it. She was fucking me clear off the bed with every thrust now and I know she was getting a real kick out of the faces I was making as I concentrated very hard on not shooting off all over myself. I felt like I was trying to make the eight minute mile. My control was hanging by a thread. She grinned and then told me I could beg to cum if I had to. I begged like my life depended on it. She asked me a lot of questions – did I love her cock? Was she fucking me how I always wanted to be fucked? Would I need this again and again? Of course the answer was yes and I gasped it as loud as I could. Then she asked me to cum for her and my body was like a bird fleeing the cage when the door opens. I squirted and squirted as she kept up quick little encouraging thrusts right onto my spot. I was clutching handfuls of duvet and wailing for minutes as she slowed and cooled down.
Then came that lovely quiet with the undulations of bliss passing over my skin as I lay there, bound to her, as I babbled happy nonsense and she fed me my cum on offered fingertips. She stroked my brow, experimented with a pulse of naughty thrusts to spike my heart rate and I praised her like I’d never praised anyone before. My heart felt like it might melt from gratitude and joy.
We carefully separated and she made us oven pizzas while I showered up. I remember being curled up on the couch downstairs in my stockings and silk nightie and being completely disbelieving that something so great had happened to me.
After dinner she showed me exactly how to eat her ass.
…
Feels good to share a story like that though it did make me awfully nostalgic. If you’ve liked it, drop me a line in a comment or DM to say so – you might have got the sense that I do like encouragement.
Source: reddit.com/r/gonewildstories/comments/cigii2/31_my_first_pegging_dommed_dressed_up_then_dicked
I haven’t read anything so hot in awhile. Amazing ??