First time poster here so let me know what you think and if you would like more, thanks.
I was feeling adventurous one day so decided that I could try my hand on Craigslist, so I made a posting saying that I was looking for a good fucking with anal play etc. Naturally the emails came flooding in from everywhere, most were just people saying meet now. I wasn’t willing to meet right away so they were out, and after about a day of nothing but weirdoes, I was about to give up, but then I noticed an email from a guy, Alex, who said that he loved my photos, but lived a fair bit away from me all though he was going to be spending a night at a hotel in the city center in a few weeks and would like to meet up then. He had attached a few photos of himself, he was nude older ladies than me, probably around 30 , but pretty hot, slim build but relatively muscular, of course there was a dick pic, but it was actually quite nice, his whole body not just his dick which was a change than most I'd received.
I replied that I liked his photos mature older women thumbnail too and I wouldn't mind meeting up but would want to get to know him a little first, and included my skype name. Within five minutes of sending the reply I got the notification that he'd added me on skype, after accepting we started messaging back and forth. After getting to know him a bit, and some erotic video chat I was pretty sure that I wanted to meet, Alex said that he could make me have the night of my life but I should follow some instructions to prepare myself, naturally I agreed and we arranged to meet the Friday in a weeks time.
Between the and the day itself me and Alex kept skyping almost each night and I even tried out my new sex toys for the first time on cam for him. Just before I had made the posting up on Craigslist I had decided that now I don't live at home anymore I can invest in some toys for myself, and ended up ordering a little bullet vibrator, dildo and butt-plug, the perfect things to spend my student loan on. But after loosening my ass up with the dildo and easing it inside me for the first time I realized how good it felt. Alex immediately suggested that I try wearing it in sometime I was out in public and added that to his list of instructions for the big day.
The day itself I had class in the morning but I was finished at around 1pm and was to meet Alex at 5pm, so I got started on his instructions. The special instructions I’d been given were: I need to be freshly shaven, which I did that morning in the shower, then I was to play with myself and edge a couple of times throughout the day. So after class I stripped down and went to town with my vibrator, but after coming within touching distance of what was promising to be an amazing orgasm for the third time, I decided that if I tried it again I wouldn’t be able to control myself, so stopped there. Next was to put in my butt-plug, this was only the second time Allover30 Free I left the house with it in, but the last time I was wearing jeans, but this time I was to wear a dress, panty-less of course. That was me, now just to walk down to meet Alex; we had picked a coffee shop in a busy shopping center. It was about a 10 minute walk from my house, but in a dress with no panties, I was terrified that the butt plug was going to slip out, even though it was well inside me, but I guess that just added to the excitement.
I got to the coffee shop and texted Alex, who replied that he’s be a few minutes, so I grabbed myself a coffee, and sat down to wait for him. The chair was one of those hard wood ones and whatever way I sat down on it the butt plug moved unexpectedly, at this point I had forgotten that I was wearing it, so it was one hell of a shock, and I was so horny I almost came there and then. I sat there watching the door of the shop for Alex, feeling my freshly bald pussy dripping in anticipation.
Five minutes later he walked in, and as soon as I spotted him I jumped up and ran over to greet him, the motion made the plug move some more, that combined with my horniness and expectation sent me weak at the knees and I pretty much fell into his arms. He got himself a coffee and we sat back down at the table, I was careful this time not to move the plug too much, as it could well have send me over the edge this time.
When Alex asked me if I was looking forward to later, I told him that he was bang on with me wanting to get fucked from the instant I seen him. He just smiled at that and said something along the lines of "There’s a lot more teasing to come, by the time we get to the hotel you’ll be a horny mess" That just made me feel even better, but I was only just restraining myself from dropping to my knees and begging him to fuck me, so I wasn't sure how much longer I'd be able to take it
We finished up our coffees and then he said we should go for a little walk, and as we left the shop he held the door open for me, and walking up behind me gave my butt a cheeky little squeeze before grabbing my hand. He was right I was nude women over 50 a horny mess. He had told me we would do a little shopping before dinner, we walked for a few minutes more until we came to a Victoria's Secret and Alex told me that I could get whatever I wanted from here. Being the innocent 19 year old that I was, I had never even been in a VS before, let alone bought anything from them, so I was like kid in a candy shop. Ended up buying a sexy bra and thong set and a set of stockings. Alex paid for the lot.
With me delighted with my new purchases we headed off to dinner, Alex held the door and cupped my ass again, but this time he found the bottom of the plug and pushed it around a bit, when he did this I let out a little involuntary squeak. It wasn’t that long of a walk to the restaurant, pretty fancy, again paid for by Alex. During the meal he would sometimes just look right into my eyes, which just made me feel that I was going to melt.
After dinner we made our way to the hotel and up to the room, It was only a standard double, but that would be plenty for our needs. Once we were in the room and the door was closed, I pretty much flung myself at Alex and pressed my lips onto his, it wasn’t long until our tongues were exploring each other's mouths. Alex's hands started to move down from their original position just below my shoulders and down to my ass and squeezing my cheeks, then one of his hands found the plug like before, but this time wasn’t just a gentle push, my knees instantly went weak and I couldn't help but let out a little moan. As one of his hands kept playing with the plug over my dress, his other moved round and reached under my dress and started rubbing at my bare pussy, "My God" he pulled away from kissing me for a second, looking right into my eyes again "You’re absolutely soaking" slipping a finger right inside me as he said it. "Uh-huh..." was all I managed to moan out. Alex was right, this probably would be the best night of my life, and I was only in the door!
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