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.
Tag: BJ
Blowjob Tutorial [MFF]
So to start this off, I feel obligated to say that I’ve been a long-time lurker here, and haven’t contributed much. I’ve always read these stories and felt a sense of longing, like I’ve been missing out on something new. Honestly, I never thought I would contribute anything—however I’m so happy to tell you I was WRONG.
Fuck, just trying to type this out gives me jitters. It happened a couple weeks ago, and the more I’ve thought about it, the more I realized I need to write this down to remember it for the future. This is a bit of a long story, so if you don’t care to read the back story, skip down to the part that says THE DANCE FLOOR. For obvious reasons, this is a throwaway account. Also, I did the best I could to paraphrase the dialogue, but I couldn’t quite remember everything that was said verbatim.
Sex in the shopping mall [MF][Public]
So my fiance arranged a threesome with another girl for me for my birthday. I was blindfolded the whole time, but guessing from some circumstantial evidence, it was one of her best friends, who my fiance, Ellie invited into our bed. It was an insane experience and the other girl even went as far as to swallow my whole load, which is the biggest turn on for me. I am getting hard thinking about it alone.
Some readers said I’d need to repay Ellie for that experience, by fulfilling one of her fantasies. They were right of course. It wasn’t that easy though to settle on something, as Ellie decidedly does not want sex with another man or girl for that matter. Her biggest kink however is having sex in risky places, where you can get caught at a moments notice. Well, it isn’t something I am that comfortable with, but what the hell.
It took a few days to muster up the courage to actually go through with it though. So we decided to screw each other at a shopping mall nearby, which had a bunch of nooks and crannies to exploit.
[GAY] [M][STEAK M] A sorrow of the mind and a love of the night: A steak story.
It was a beautiful night under the starry sky.
Daniel, and his loving, caring boyfriend were sound asleep, cuddling with each other in bed. Daniels boyfriend, of course, is his most beloved, lusted after thing in the entire universe. His name is Zenith, an anthropomorphic prime beef steak. He is absolutely ripped. He is 6’7″, has sexy, muscular arms and legs, a six pack, abs, and a huge, meaty cock.
Daniel always drools from lust when sleeping with Zenith, but that’s no problem, drool is nothing compared to all the steak grease and cum seeping the sheets. They are having a peaceful night: cuddling, sleeping, kissing a little, just like they always do, but today, Daniel has a nightmare.
“AAAAAAAAHHHHh!!” screamed Daniel out of the blue. He followed by sobbing hysterically.
“Ssssshhh… come here honey… calm down… it’s ok, baby boy,” comforted Zenith softly. “What’s the matter, sweetheart?”
“I…” he is shaking in despair. “I had a d-dre d-d-dream about sniff my daddy molesting me again! sniff”
Zenith deals with this a lot. He knows about Daniels dark past, but he is always there for him. He loves him.
[MF] My physical exam partner, the MILF
I started an advanced medical practitioner master’s program over the summer. I was 26 when we started in July and recently turned 27. I’d been working up to this for a number of years, and was thrilled to finally begin. When we started, I hadn’t been in a classroom for over four years, so it was a big change and has been quite difficult at times. There are about forty students in my class, most of them my age, but some younger and some older. We’ve got about 60% females and 40% males just to give you an idea of the class environment.
Anyways, the summer term was all review from undergrad, but at a vastly accelerated pace. The weeks flew by with two or three exams per week and all of us hanging on for dear life. Needless to say, as a part of this process, we all found our friend/study groups. I gravitated towards some of the more serious students in the group, a couple other guys and three or four women. We’d work in the cadaver lab together, study for exams together, share study guides, etc.
7 Day Sex Challenge from my Wife [MF]
ey all – we are a married couple in our early 30s with two kids under the age of 5. Our sex life is still great but out of pure exhaustion and scheduling we typically have sex 1-3 times per week.
The other day, my wife challenged me to see if we could have sex 7 nights in a row. This was like music to my ears! I thought it would be fun for us to update you as we go. We both think the last time we had sex every night for a week was when we started dating in college.
Night 1: We started out by watching a video while I fingered my wife and she stroked me. We were both super turned on so it was probably 5 minutes before she turned toward me and away from the TV to start giving me a BJ. I ended up flipping her over and fucking her doggy style. She reached back and start rubbing my shaft while I thrusted while I reached around and rubbed her clit at the same time. After she came once, I picked up the speed to get towards finishing myself and she ended up having a second orgasm before I finished on her back.
The Roommate: Revisited
The night was at an end and I opened the door to my apartment. My date had gone well but unfortunately she had been reluctant to come home with me. I had had a bit too much to drink and I ended the night with an awkward kiss and made my way home alone to take care of myself for yet another evening. I tossed my jacket onto the couch as I walked to my bedroom. I got undressed and left my clothes on my bedroom floor, making my way to the bathroom for a long shower. My roommate was out for the night so I didn’t bother bringing any clothes or a robe into the bathroom with me. I turned on the shower and soaped myself, thinking over the night and wishing that my date had come back to my apartment with me to take care of the situation I had going on in my crotch.
I turned off the water and looked down at my raging erection, realizing that I had to do something about it soon before I got too excited. I pulled the shower curtain open and, as I reached for the towel that hung on the wall beside the sink I noticed I wasn’t alone in the bathroom. My Roommate was standing in the doorway, eyes fixated on my boner and licking his lips.
Mile High Club Madness [MF]
Sometimes life is crazy.
A few months back I was on a red-eye flight from the West Coast to Philadelphia. I had an aisle seat a few rows from the back of the plane.
The window seat next to me was empty and I thought I might luck out and have the extra space. No such luck, the last passenger to board was a middle aged woman in a black sweatshirt that read ” Soccer Mom” with one of those tiny yippy dogs in a little cage. I was pretty tired, and thought I hope this dog doesn’t yip the whole flight.
She was nice enough, with a deep NY accent, but a bit annoying in a high maintenance kind of way. First she asked for help put her bag up, which was fine but then she wanted to talk. We chatted for about 20 minutes about her kids, etc and she bragged about the Eagles winning their first Super Bowl.
I told her,” It was a great game, I have some meetings in the city tomorrow, so I’m going to try and sleep.”
Like public sex, piss and rimjobs? This is for you [MM]
I’ve always been bi curious, and very kinky, but never had a way to explore it. That was until
my coworker started aggressively hitting on me, and finally convinced me to come over for drinks. Fast forward a few months and we were constantly trying to top our kinkiest fantasies. He was very open immediately about his kinks and it allowed me to be comfortable sharing mine. My two biggest were public sex and water sports so we decided to give it a shot…
We drank A LOT of beer (have to fuel up) and went out to a park nearby around midnight. It was very close to a busy street but big enough that we could have some distance away but still see the cars passing. We walked around a bit and found a huddle of trees that provided decent cover. Not great though, just cover from the street, had anyone walked up on literally any other side of us they would’ve called the cops.
Our First Time [MF][Rough]
Posted this elsewhere, but after doing all that typing, I wanted a backup somewhere.
The roughest was the first time with this particular guy, but we had been talking and texting daily for over a year, had met in person for dinner and to hang out for a day before, and were very, very comfortable with each other. We had also talked about limits, kinks, safewords, what was and wasn’t ok, etc at length. Although the uncertainty and “stranger factor” probably did help make it hot as well.
We met at a motel and I had made a point to dress up – short skirt, heels, stockings & garters with nothing underneath. He walked in, we hugged, we kissed, he grabbed me by the hair & put my on my knees. It quckly went from a blowjob into straight-up facefucking. I swallowed his cock down to his balls, so he pulled back out then slammed it it, while pushing my head down. He held me there for a while as and after he came, trying to make me gag (I wasn’t sure, but he told me later he wanted to see if he could make me puke on it). Then he had me strip and was calling me his dirty fucking whore and all sorts of things while I got naked and fingered myself for his amusement.