The oldest guy I’ve been with was 48, this was a couple years ago when I was 16, though I didn’t know his exact age till after… I guess I should start with how we first met. I was at the mall getting some new outfits, and when I was in Nordstrom had a guy come up to me that I know had been watching me for a little bit. I was looking at this little black dress when he came up to me.
Him: “that dress would look fantastic on you”
Me: “you think so? I’m not sure if I have the right figure for it”
Him: “oh absolutely, why don’t you try it on and I’ll let you know how it looks”
So, i said sure, and went into the changing room to try it on. It was a very tight, short dress, with a low cut v-neck. When I came out he said I looked amazing, but agreed with me when I said I’d need a pushup bra to really fill the dress properly. I tired on a number of outfits, and he picked out the ones he thought I looked best in, but said he was dissapointed that he wouldn’t get to see me wearing them when the outfits were completed. I was planing on getting everything for a complete outfit, but he wouldn’t have gotten to see it as I wouldn’t be trying on everything at once until I had gotten home. It was at that point he suggested I come over to his place after I was done shopping so that I could model the outfits for him. I was nervous at that idea, but it sounded like fun too, so I said ok. We spent a bit more time shopping at a few different stores, and I picked up everything to complete several outfits, modeling most of it with the exception of the bra’s and panties I picked up at Victoria’s Secret. Several of the outfits he insisted on buying for me, I tried to tell him that he didn’t have to, but to be honest it made me feel good that he was buying them for me, I mean who doesn’t like someone buying them gifts?
Anyways, afterwards we carried the bags out to his car and then drove back to his place. He carried my bags into a room where he said I could change, and then went into the living room (which was right next to it) to wait. I got dressed (had gotten a number of complete outfits, dresses or tops/skirts, heels, bra’s/panties, and even some stockings to complete a couple of the outfits) and went into the living room to model for him. He said I looked fantastic, had me turn around for him, do different poses, then come over to him so he could look closer at how the outfit fit me. Things moved from him just looking, to him touching me.. moving me in how I was posing, or adjusting how the outfit was fitting me. As I tried on different outfits he got bolder with his touching, instead of just pulling at the edges to adjust, he would put his hand on my butt or breast saying he was seeing just how the dress was fitting me, running his hands over me.. I liked the attention. He would have me bend over towards him to see how the top fit, or turn around and bend over so he could see how the dress/skirt fit me.
The final outfit was probably the most daring outfit I had bought during the day, and one he had encouraged me to put together. It was a tight black mini-skirt, black lace tube top, black stockings, black lace thong, and black/red lace strapless pushup bra, with a pair of 5″ black stiletto heels. The skirt just barely cover the tops of the stockings when I was standing, and when I walked out in it his jaw dropped.. which made me smile.. and he said I looked perfect. He didn’t have me model it long before he told me to come over closer, and he was even touchier than he had been before, pretty much just feeling me up. He said there was one thing wrong with the outfit though, I asked him what and before I had a chance to react he reached up my skirt and was pulling my panties off. He pulled them down and I stepped out of them, and he said there.. now the outfit is perfect, which made me blush. He stood up, I’m short so he was quite a bit taller than me, even with the heels, and bent over and started kissing me and running his hands over my body. I’ve always loved kissing, and I loved the feeling of him holding me. It wasn’t long before he pushed me down to my knees and undid his pants, and had me suck on him. He was already pretty hard, and it wasn’t much longer before he pulled me back up and pushed me back against a table, sitting me on it and spreading my legs. There hadn’t really been any foreplay, but luckily I was quite wet, though it still hurt a good bit when he pushed inside me and started ******* me. It hurt (I’ve always been very tight) but felt good too. He pushed my tube top up, and pulled the cups of my bra down so he could see my breasts and he started playing with them while ******* me. Sometimes he’d move my legs up over his shoulders, which I could feel him go even deeper when he did. When he was about to finish he started going faster, then pulled out and pulled me off the table and onto my knees, pushing into my mouth and *******. After, i cleaned up and changed back into my normal clothes, then he gave me a ride back to the mall where I got a taxi home.