Amateur Picture Galleries - The Amateurs Gallery Diaries

So I'm 26 now, but this happened my senior year of high school, when I was 18. I was a senior in high school and I was dating a sophomore who was 16. It was great, she was hot, but I've always had a fetish for older women. One of my friend's mom, Abby, was one of my friends on AIM. We were also Myspace friends but we only spoke on AIM. We chatted on AIM because I was in a band and so was Abby's son, who was my buddy, and compared notes about local gigs we played and potential recording studio possibilities. It was all pretty innocent until one night I felt bold and comfortable enough to karup galleries let slip that I liked older women. She would say stuff like "I bet you get plenty of girls your age," but I would persist that I would still prefer hooking up with someone older. At the time, I was 18, 6'3", slim, in good shape, about 180 lbs. and had no trouble getting girls to like me. She was in her late 40s, probably like 47, about 5'7, a tad overweight with curly brown hair that went down to her shoulders, and huge tits. I've read tons of these stories on this site and every story says "she had 44 DD's, massive tits!" but she really did have huge tits, probably because she had a few extra pounds, but she didn't have much of an ass. Anywho, after a couple weeks of flirting, and some persuasion on my part, we finally made a day to hook up. She worked as a hair stylist at a local salon, which also happened to have a masseuse, so she made arrangements to keep the place open after hours, and to give me a massage. We met on a Friday, around 7, after the place had closed. She unlocked the door and let me in, and I was fucking nervous. I had only had sex with two girls at the time, one of which was the girl I was currently dating. She was wearing her normal clothes, nothing special, just some jeans and a white t-shirt. We said our hellos, including a slightly awkward hug, and she told me to go the massage room, which was down the hall, and to strip down to a towel, and then lay face down down on the massage table. After removing my clothes as fast as I could, I put a towel around my waist, and layed down on the table as instructed. I waited just a few minutes before I heard the door open and Abby step in. She put some corny massage music on the stereo and then started to slowly rub my back. As far as a massage go, I'm sure it was pretty bland (I've never had a professional massage in my life) but my 18 year old self loved it. I was almost instantly hard which was awkward because I was laying on my stomach. After a few minutes, Abby told me to turn over onto my back. When I did, I finally saw that she had stripped down to a white lacey bra and matching thong. Needless to say, I was pitching a tent in my towel. Abby noticed this and slowly slid her hand down to my hard cock. As she did this she leaned her face into mine and whispered "Are you ready?" Without waiting for an answer she pressed her lips onto mine and we started making out. It was so fucking hot. My tongue was in my friend's mom's mouth, and she started stroking my cock. I'm a little over 7 inches, uncut, and she was stroking every inch of me. After forcing my tongue into her mouth, she pulled my towel off and kissed down my body, and then slid her lips around my cock. To this day, she is the only girl to ever take my entire cock in her throat. She put the whole thing in her mouth, gagged a little, then let my cock slip out her mouth. She then spit on it (a first at the time) and started stroking me while coming back up to make out with me again. I then unclasped her bra and let her titties fall free. She shoved her tits in my face and I licked and sucked on her nipples, which instantly became hard in my mouth. She then returned focus on my cock. She would pull my foreskin up and lick inside of it, on the head of my cock, before going back to throat me. I remember thinking she might have perfected this technique on her husband because it was something completely new to me. It was some fucking pornstar shit and I'll never forget it. I then sat up and swung my legs off the side of the table and she bent over and kept sucking me. I pulled her head off my cock and made out with her while sticking my cock between her enormous tits. Her tits fucking devoured my cock and it felt great. At this point, I was about to cum. I told Abby that I was close and she just stuck her tongue further into my mouth and squeezed her tits tighter. I started cumming between her tits, hitting the bottom of her chin, all while continuing playing with her tongue with mine. We continued making out until Abby said "I should get cleaned up now," to which I responded something along the lines of, "I'm 18, I'm not done yet." That seemed to turn her on and she stared going down on me again, and being 18, I was hard again super quickly. I hopped off the table and reached down and pulled her thong off. She had a tad a bush but that was kind of hot, because having a bush is kind of a "mom thing" so that turned me on. I turned her around and bent her over the massage table. I then lined my cock up with her pussy and slowly slid in. She let out a deep moan which got my confidence up, and started to quicken my pace. I put both my hand around her and squeezed her tits, then pulling her up so we could make out while I fucked her, my cum still on her neck and tits. We fucked in the position for a few minutes and she started saying, "make me cum, fucking make me cum, fuck me with your young dick." I shoved her face down onto the table and grabbed the back of her neck and started saying some pretty dirty shit to her like, "take this young cock, cum for me you milf slut." With that, she started to cum, legs shaking as she pulled herself off my cock. She fell to her knees and immediately took my cock back in her mouth. I then leaned down to make out with her again (I'm into making out, did you realize that yet) and whispered to her to make me cum on her face. She stroked me as hard and fast as she could and then I took over and came all over her face and parts of her hair. I was then looking at my friend's mom, covered in my cum, and bent down to make out with her for a bit more before she cleaned up and we got dressed. We ended up hooking up once more, with some anal (if you're interested) but after the second time she said she felt too guilty to be fucking her son's friend so she broke it off. Kinda long, hope you enjoyed. onetime0034 [1 comment]