Tag: Straight

I know I know ,what the hell was I thinking?! But I thought it was a good idea at the time. (I’m 26 now and this happened when I was 22) I’ve had 3 girlfriends before her but we never got around to having sex. They wanted to wait and honestly I did as well. But at 22 with no girlfriend and my virginity still intact, I was done waiting. I wasn’t really interested in anyone in my College and I would go out with friends to bars and whatnot but never wanted to just “pick someone up”. So I turned to google and looked up online dating and something caught my eye. A link to sugarmomma dating. So me living in Palm Beach Florida where a ton of rich people live figured why not? I post a picture of myself and some info(I was athletic and worked out twice a day 5 days a week. In a week I had someone contact me. She was 44 and single. We chatted for several days and she wanted to meet up for what she called an “Interview”. I was actually pretty calm and excited to meet with her and did so at a restaurant in downtown. She looked pretty hot for someone who was 44! She was about 2 inches shorter than me but had a killer butt and her boobs were more than likely fake but who cares? She was actually pretty chill and had a great sense of humor and she asked how many other rich women I’ve had the pleasure of being with. When I told her she was my first, she had a huge smile and said I’d love it. We chatted for awhile longer and I knew I had to tell her. We got back to talking about how she would be my first sugarmomma and that’s when I told her she would be the first woman ever. I didn’t know what to expect but her eyes widened and her jaw dropped. She placed her hand on mine and said “I’m going to change your life”. I was super excited but it got even better. She was asked if I’d like to accompany her her on her 2 week vacation to Puerto Rico at her vacation home. I wasn’t sure though (I had a decent job and Bill to pay) but I told her my job I had and my bills like car payment and small student loans and she assured me that it will be taken car of. I managed to actually get 2 weeks off of work so that made me feel a bit better with leaving. About a month passes and it’s finally the day to get on our flight. It’s not a private jet or anything but it’s first class everything. The first day starts out great! We get top notch dining, charter a tour, and some jet skis. Then in the early evening things settle down a bit and I’m actually nervous inside but I try to hide it by making some moves as we’re over looking the ocean at the house. I pull her in for a kiss and immediately after she says “Someone’s feeling rather confident” and I knew she saw right through that. She grabbed my hand and took me inside and she told me to just sit there and she’ll be back. At this point I’m dying inside of both nervousness and excitement. She comes back completely naked with some condoms and I’m in shock right now. She’s gorgeous and I’m still sitting on the couch fully dressed. She unzips me and I’m obviously already hard as can be and she pulls it out and just hold it in her hand and stares at it. She says “you’re already drooling” and I’m confused and then I realize I have a ridiculous amount of precum dripping. She just literally plays with it for a while and I’m sure I looked like an idiot just squirming around while she does that and she’s just amazed that I keep producing so much precum. (I guess that’s not normal?) Then she just sucks on it and I’m in heaven! I thought I was gonna cum right there but she stops and gives me the condom and asks me to put it on because she wants to to get on top. I’ve actually never put a condom on before and apparently it was pretty evident as I was failing miserably. She tells me it’s ok and to just lay back and relax. She leaned over and kisses me and then I feel her lower herself onto me and it felt so warm and wet! That’s when I noticed she never put the condom on but I I couldn’t do anything about it because about a minute later I told her I was gonna cum and she said to just relax. I’m sort of panicking because I couldn’t hold it but she just stayed on top of me and I came inside her. I just came inside some woman who is 1 year younger than my mom. It felt amazing but I felt weird. She hopped off and kissed me and I almost immediately got hard again. She noticed and she told me to fuck her. So I did and this time lasted a bit longer but the same result. After we go to the shower and just seeing her naked there gets me hard and so we do it again in the shower. We get out and dry off and to the bedroom and boom! I’m hard again! So we go at it again. I’m exhausted at this point and so we doze off for what I thought would be the end of the night. But not 10 minutes later I feel her playing with my dick and she looks at me and says “you were hard again so let’s keep going”. And she just climbs on top and rides me like she just got a jolt of energy! I came again inside of her. She just cuddles afterwards and I get hard yet again and we do it one more time. All in all on my first night I came in her 6 times. I was so spent I felt like dying. The next morning I felt exhausted and she woke before I did and when I was getting up she came in the room and gave me a blowjob and had me fuck her again. I’m not gonna lie, my dick was sore. I didn’t know that could happen but after awhile it felt good again and I came in her. We did it 4 more times before we left the house and didn’t it more when we got back. She was just using me nonstop day after day. I didn’t know It was physically possible to come that much in that amount of time. And 90 percent of the time it was inside of her. Out and about we talked like great friends and she bought everything and it was great but at home she just banged my brains out! She just wanted me to fuck her anytime I could get hard. After about day 5 I told her if we could take a break. She apologized and said she got carried away and that she would take care of me and just kept reassuring me that everything would be fine. It changed nothing. She went straight to it as soon as we got home. If I was just relaxing and she wanted it, she would just walk up to me and just start touching it or sucking it to get it hard and then pound it out again. She even bought toys that I didn’t know existed for both me and her. This whole trip had me shook and I was way in over my head. After the first week she got more and more aggressive. She talked more and more dirty and she even teased me when we were out in public. She would give me awkward boners in public and she loved it. I kinda did to because all the guys would stare at her because she would dress provocatively and then she would just throw herself at me in front of them. In those moments I felt like the man! But at the house she would take control of everything and she even told me that I was gonna fuck her in the ass the next day and all I could think was “this is getting out of hand, I’m not ready for this”. But the next day comes and she wakes me up the same way but then bends over and pours lube on my dick and her ass and tells me to stick it in. I do and it was ridiculously tight and I was so sore that I thought it would never work but then it just slipped in. It was different and a hell of a lot tighter but I was just so sore. I lasted long though and it was probably 30 minutes before I came in her. And this all continued the rest of the trip. As we got back she wrote me a check for my student loans and paid off my car. I owed 7k on the car and 11k on student loans. But I was in a daze as I got back to my real home. I was exhausted mentally, physically, sexually. I felt some regret though that I didn’t lose it to anyone special. It was great at times but more traumatic than anything because I didn’t know my body could withstand that. Although I did see her a few times after but never for more than a night. She would ask me to go on trips with her but I couldn’t. I’m not doing that again. I asked her one day though as to why she didn’t use a condom? And she told me that it was obvious that I was a virgin because I looked like an idiot trying to put the condom on and she had her tubes tied after her 2nd child. I told her that after the trip I was worried because I put probably 2 gallons of cum in her. After everything from that trip I’d say it was definitely a learning experience. I learned how to go down on a woman and do it well. I also learned that I never want to do a trip like that ever again! Lol. Not my best choice but it did pay off in the end. Literally.