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I made the mistake of sharing this story with a friend who turned out to not be much of a friend at all. I can look back on it now and laugh, but at the time I was a much different person, and as you may have guessed, the story got out. It was incredibly humiliating, however, I know now its really not that big of a deal for a horny teenager. I am M.
pounds over weight, shy, kinky as hell, masturbating twice a day just would not cut it any longer, so to craigslist I turned. I was honest, "eager, young, shy, high school kid looking to loose his virginity." I was about as bold and honest with the title as I could be. The thought of being turned away at the door was unbearable, so I wanted to be sure everything was out on the table. million selfies or so later I found one or two that were acceptable and the ad went live. I was positive someone would recognise me, but to be honest, I was so desperate I didn't think twice about it.
Several days later, not a single response, I was feeling pretty low. I never really expected to have any success, but it was still a bit of a let down. I knew I could always ask a girl out, there was one I was sure would say yes, but living in a small town, I just didn't have it in me to risk asking. So, at this point, I have come to terms that I was simply going to die a virgin.
Another few days pass, and it happens, a response! The response was about a day old, I feel like vomiting that I didn't check my email and may have missed my chance. I had created a brand new email strictly for this endeavor, so I didn't get the typical notification. After ten or so minuets staring at the email I get the courage to open it.
I tried to recover the old email account to post the conversation, however, I was unsuccessful. I did save the photo she included in the email to my laptop and I managed to dig it up, so here it is.http://ift.tt/IYokVy
I remember she was very sweet and respectable. Reflected on her own experience, told me she was once in the same spot as a kid and was happy to help me out. She told me that I had to be careful meeting people online and said we should meet first. I agreed, of course, and she invited me to a local coffee shop. I really couldn't see much in the picture, but it didn't look so bad. She had told me she was "an older woman for a guy my age" but I was totally fine with this. Hey, I could say I banged a MILF, this would have been a big deal when I was a kid. So we picked a date and time and that was that.
Fast forward days and I got an email from her telling me what she would be wearing. I managed to find her at the coffee shop, she got up and came over to me before I got to the table and gave me a hug. It was really awkward, for me at least, but I was relieved a camera crew didn't come running out from around the corner, so we were off to a good start. She was decent looking. Far from a knock out, I would call her a .- for a women her age. She didn't have a very pretty face, but she had a surprising nice body. She had a a tight butt, I was sure to check her out when she turned around to lead me back to the table. I have always been an ass guy, so seeing that pretty much had me hooked. After we sat down we shared names, had the typical small talk, and then she got really dirty really fast. She was speaking kind of loud so I was super awkward, but I went with it. She started to ask me particulars, fetishes, so on and so forth. I admitted to her I was interested in the more mainstream stuff, lesbians, threesomes, asses, the stuff most guys like. However, I also shared that I was interested in crossdressing and bondage. I had thought of both of these as really strange fetishes at the time, so it was a big deal to share that, it was the first time I had shared that. She told me she wasn't interested in bondage at all, but thought the crossdressing was cute. After that she transitioned to something that really shocked me. She told me that she had a friend who would be interested in joining. I told her maybe in the future if things work out with her, but she started to pressure me a lot, so I gave in. I could tell she was slowly going from super sweet to more and more aggressive, but I just went with it, I wanted this more then I can describe.
Once we are done talking we decided to do it the following evening. She got up, but I didn't, I was rock hard and wanted to give it a minute. She walked over to my end of the table with a smile on her face, reach down and grabbed my dick. I grabbed her wrist without even thinking and she said something like "take your time honey". I let go on her wrist and she turned around and then adjusted her jeans a bit pulling her thong up so I could see it and then she left.
And here we are at the day of. Its pm and I head to her place. Its not far from my home, but I left an hour early just in case I couldn't find it or something. To be honest I wasn't really thinking clearly. I found the address, but I was way to early so I cruised around for a while. Once it was time I made my way to her place and to the door I go. An older woman answers the door, I mean a lot older, - for sure. I wouldn't be shocked if she was -. I automatically apologise and tell her that I have the wrong place. "Are you here for Jackie?" She says. (Jackie is the name of the woman I had met with), "yes" I mutter, and she opened the door to let me in. I get about three steps in and it hits me "Oh fucking fuck fuck fuck please don't let this be the friend". I look into a room to my left an there is jackie. She is dressed casually, jeans and a T. I was a bit disappointed, I had convinced myself she would be on a red velvet bed wearing thigh high fish nets. She invites me to take a seat and we start some small talk. I can hear the older woman doing something in another room, it was really distracting, and I was regretting my being there in a big way. There was a PS on the table in front of me, and when things got quiet I asked who owned it. "Carmelita's grandson" see tells me. Carmelita turned out to be the old lady. She asked me if I like gaming and I told her I did and started to tell her about some games I like. Mid awkward game reviews she reaches over and unzips my fly. I shut up instantly and she tell me to keep talking and relax. So I do that and she reaches in through my boxers and grabs my dick. I am still soft, I just can't focus, hearing this women in the other room is way to awkward. She tells me to relax again and kneels over me sitting on my crotch. She grabs my hear pulling my head back and starts kissing my neck. Now I am as hard as a rock once again and she reaches back and reaches into my crotch and pulls a hard dick out this time. Now she has both hands in my hair and we are French kissing. I can remember she was super sloppy. Way way too much tongue and a lot of drool. However, I was loving it. She was grinding on my dick and I was in heaven. Had both of my hands on her really tight ass, and.... Then it happened. Worst fears come turn. About minuets in... I cum. And in a big way. Its everywhere. All over her pants and mine, I can't imagine how red I am, I would have shot myself right there and then if I had a pistol. Thankfully, she was really cool about it. Helped me clean up, said it was a huge turn on that I was that into her, and she took my jeans and hers and said she would toss them in the wash.
Here I am sitting in a strangers home in my boxers and a polo. Feeling pretty caught fucking tumblr humiliated, and then this old lady walks in. I had totally forgotten about her. She walks right past me and sits down and starts reading a news paper. Then Jackie walks and and sits down and tells me this is her friend. I once again feel like puking. Now this old lady, Carmelita, is just staring at me, dead silent, and I wan't to run. How about the two of you have a bit of fun, jackie says. I don't want to hurt this old woman's feelings and say no, but its just not worth it, so I say I think I wan't to head home now, I am feeling a bit embarrassed. "But your pants are in the wash" she says, you will have to wait. And then Carmelita gets up and sits on the other side of me. Just give it a try honey, Jackie says, you will love it, trust me. And then she makes me a proposition. "You said you like gaming, correct? Well Carmelita's grandson has moved out, would you like to have his Play Station? You can have the games as well, there is no use for them. Just give it a try, and when you leave you can have it." I paraphrase a bit, I was pretty emotionally freaked out, but that was the gist of it. This woman had just offered me a PS to have sex with some old lady in her s. Tell me a week ago a woman would give me a PS to have sex I would have been stoked beyond words, this was far from that fantasy, however. I stand up, I was just going to leave, and Jackie gets up and stops me. She goes in for the kiss, I kiss her back, and she pushes me back down to the couch, her kneeling over me just as before, and we keep kissing for a few minuets. Then she tells "how about she just gives you head?" I will stay here you won't even see it." And I shamefully agree. As soon as I said ok she starts kissing me again and Carmelita is reaching into my boxers. She didn't waste a second and she was sucking. I admit, it felt pretty amazing to be kissing Jackie while getting a blow job, I kind of just put the context out of mind. Then it hits me, I don't have a condom on, and I kind of push away from them both and tell them that I need to wear a condom. They both start laughing and say they are happy I am ready to move on to that. Jackie had a condom in her pants and puts it on me. I then look at Carmelita and she is taking her skirt off. I am pretty freaked out, but I guess it was a combination of me enjoying Jackie and the PS that kept me going.
Well, there is no pretty way to say it. This old lady does not waste time. Before I could even get a word out she was on top of me. I can't even look her in the eyes, I just keep looking at Jackie. "Get ready to loose your virginity honey" Jackie says, and then she passes Carmelita a bottle of lube. She squirts some on her hand, rubs it on my dick, and a few seconds later I was a virgin no more. To be fair, it felt fine. I was pretty disgusted with myself, but to be fair to Carmelita she had a decent vagina. I never did look her in the eye, and she hardly said words that entire evening, but I did cum, She moaned a lot, and I felt like a did her a service on some level.
Carmelita went upstairs, and I sat there a bit confused I suppose, I wasn't thinking much. Jackie then started to get undressed and told me that I still had work to do. She sat down on the couch, took her panties off and told me to get on my knees and, I did, and I ate her out. She was surprisingly vocal and kept calling me her bitch and slut, at this point, I realised I was a lot more submissive then I had prior thought. She then told me to put her panties on, guess she remembered I liked crossdressing, so I did. She ended up telling me to leave them on, and I admit, I kept them. A see through yellow material with white polka dots. At this point I was pretty happy with myself, the panties were a huge turn on and Jackie seemed to love it, I was now in the zone. She then flips over and tells me to lick her ass. Without a second thought I bury my face in it and start fingering her. I hear Carmelita enter the room but at this point I could not care less and keep to my work. Jackie is literally dripping wet so I feel pretty fucking proud of myself. Once we are finished up with oral we make out a it more, I was a bit surprised she wanted to after my tongue was in her ass, but I was fine with it. Then she told me I was great, and ran out of the room. Came back with my jeans, told me I could go to the wash room to clean up and get dressed. Once I got back down stairs she passed me the ps in a bag, kissed me on the cheek and said I was a great sport and hope I enjoyed it. I thanked her, left, and that was that!
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