[MF] Shy college graduate and his first MILF

Contrary to popular belief, not all college students party all day and get laid all night. Between trying to keep up the grades in class and working part time to attempt to afford enough ramen noodles and water to survive, there was really no opportunity for me to explore my sexuality. Couple that with the fact that I could be pretty shy around new people and you get one sexually frustrated college graduate ready to take on the world, haha.

Don’t get me wrong. I did get my fair share of loving while dating a couple of sweet girls in college but i never really got the opportunity to truly explore my sexual desires and fantasies.

I had just graduated college and it was time for me to experiment before real life takes its toll. My biggest desire I wanted to cross of my list was to fuck a hot MILF. No! I did not just want to fuck a sexy cougar, I wanted to go with her on an erotic adventure.

I’ve always had a thing for women older than me. There’s just something about your next door house wife neighbor that i see in every sexy milf that I find so erotic. She would be open minded, ready to explore, wiser for the age, maybe even teach me a few tricks. I just imagined that if I found the right MILF I could make all my fantasies come true. Now I just had to find her. This was going to be perfect!

But where do you search for unicorns? The internet of course… on second thought, you would have a better shot trying to pick up a cougar at your local target or at a bar, especially if you have a bit of confidence, vigor and don’t mind public rejection. My case is a little different. Bars are not really my scene, I’m more of a hang out at home with friends, and have a couple of beers kind of guy. Picking up women at bars, much less cougars, is out of my element and in my mind, if I don’t feel comfortable, I won’t be successful. On the other hand, I don’t have the cojones to start asking the local target housewives for dates, haha. That’s just creepy. So, the internet it is. I was going to create some profiles with some hook up sites and find me a sexy milf. This was going to be perfect!

Messing around with the hook up sites was as bad as you might expect. Online dating is already lame, try specifically searching for cougars and it becomes twice as bad. After several months of unanswered messages and failed cat phishing attempts on my profile, I had pretty much lost hope. I was never going to find my perfect cougar. I give up. If it happens, it will happen naturally. I closed down most of my profiles, I left just a couple, that I periodically check out of boredom. I get the occasional message from fake profiles or from guys. Like this one message that I got from a “50 year young female”.

“Wow sexy stud, put that big hard tool in my pussy or ass and we will be alll good”

This is obviously a scam. It’s a fake profile or a guy. Women don’t message guys like this. Dealing with hook up sites bull shit for several months will teach you how to spot fake profiles pretty easily if you have half a brain. First red light: overly sexual message initiated by a female. Even so, My curiosity was peaked enough to where I explored her profile further. Her profile was normal. Normal pictures, no nudity. Normal bio, no obviously fake descriptions. I look for other small signs that this is a real, genuine person. There’s a light at the end of the tunnel. Everything seems to check out. She looks great in her pictures. She was smoking hot, but she wasn’t without her small imperfections, which made her even sexier to me. You could almost see her fun loving personality through her charming smile and raven eyes. I’m still very cautious, but I bite. I respond with a playful reply to gauge her reaction and go from there.

“Hey sexy girl… I will gladly oblige, as long as you put your booty in my face and your pussy on my tongue first.”

She responds by sending me a sexy pic of herself, fresh out of the shower, with a towel only covering her hips and thighs. Her smile looks even better, it’s much naughtier when she’s naked. You can tell she had fun taking that picture and showing it to me and anyone else she might have shown it to. Her exposed breasts looked amazing. I love big tits as much as the next man but her B-C cups were some of the best I’ve seen. The were hanging a little bit which I loved, I imagined them dangling in my face which also got me hard immediately. Her dark nipples were like chocolate treats for my eyes. If I vibe with her mentally the way her pictures make it seem, this was going to be perfect!

“Promise you’ll also give my lips and tits some attention first”

You don’t have to ask me twice. This is too good to be true. I’m thinking there must be something I’m missing, but after exchanging some emails over the next couple of days, everything felt right. We continued texting and sexting over the next several weeks. We both wanted to get to know each other, sexually and non sexually, before we committed to any erotic encounters. Meeting people online is very sketchy, we both excersised as many safety cautions as possible and took it slow. We took the time to get to know each other and our family situations ( we were both single ). We were going to go on an erotic adventure together and we wanted to make sure we felt secure going through that exploration. We talked about what we wanted to do to each other. As long as we were both comfortable with it we were going to do it. I told her I always thought butt holes looked pretty, coupled with a wet pussy right underneath. I told her I want to lick it but I’m grossed out by the dirty side of it. She said she’d take me in the shower and let me wash her whole body, pussy and ass. See how I liked that and take it from there. She did not mind getting her ass licked, it turned her on. She hoped that after washing her pussy and ass I will give them both a good shine with my tongue. She told me she fantasizes about me fucking her from behind, pulling her hair back and spitting in her mouth but she was too grossed out by the actual spit but very tittilated by the actual act. I told her I won’t be throwing any loogies in her mouth, haha. If she wants to try it, I was going to wash my teeth thoroughly before that and only give her a small taste of my spit to see how she feels. Our sexual communication was incredible. We were sexually starved for each other… but not for long. This was going to be perfect!

After several weeks of chatting, we decided it was time to meet for coffee and maybe get a hotel afterwards if everything went as good as it was supposed to. I arrived at coffee shop right on time. I didn’t realize how nervous I was going to be, I’m already shy to begin with. My date being 30 minutes late and the coffee house being packed to the brim definitely did not help my nerves. She finally arrived in her casual attire, looking even better than her pictures. Flaunting her sexy, phat ass in yoga pants while hiding her sexy hangers behind a flower blouse. Her nervous smile made me feel a little more at ease, I was not the only anxious one. We sat down and chatted for a minute, not missing a beat of our chemistry. She must have felt just as uncomfortable as me to suggest that we should just get out of there. Finally, a small window of privacy to grope her and give her a kiss while I walk her to her car. She was expecting that and looking forward to it judging by her eager lips and playful tongue. We got a hotel near by and met there after a few uneventful minutes. We started passionately kissing and touching our bodies as soon as we walked through the door. Her tongue was so wet and soft, we could not stop each other from sucking on our lips. She sat me down and went to open the blinds a little bit to let some light in.

“So you can get a better view of this wet pussy you’ve been craving for weeks.”

This woman is incredible. She takes off her flower blouse and proceeds to feed me her sexy hangers, allowing me the honors to take off her bra. One swift pull is all I need to unhook that bad boy and let her tits drop right on my tongue. She pulled my face closer and closer the harder I was sucking and licking her nipples. I pulled her yoga pants down as her tits were dangling in my face to reveal her bare booty looking cute behind her panties. She got down on her knees telling me she’s being craving to see and taste my big, hard cock for weeks. She pulls my jeans down and tells me:

“I can’t wait, this is going to be perfect!”

But it wasn’t perfect…. I was flaccid! I have the woman of my dreams sitting naked in front of me and I can’t even get a boner! What’s wrong with me? I’ve been jacking off to her pictures and texts for weeks and now that I have her eager to take every inch of me, I can’t give it to her. What’s going on? Don’t betray me now, penis, not like this. I guess my nerves took a tow on me, there is no other way to explain this phenomena. My sexy date, being the sweet lady that she was takes this as a challenge and gets down and dirty. This was the best and also worst blow Job I’ve ever had. The worst because I was at half chub the whole time, the best because she almost made me cum with a flaccid dick. She tried every trick in the book, bless her heart. Before I almost embarrassed myself by splurging my half chub all over her face before I’ve even seen her pussy I pulled her away telling her I want to taste her. She was happy to oblige. She laid down on the bed on her back and let me remove her panties. Spreading her thick thighs revealed one of the most beautiful pussies I had ever seen. I laid next to her and we spent the next 20-30 minutes just kissing and touching our bodies. I slowly made my way down her beautiful pussy. Her sexy landing strip was almost like a frame to her juicy pussy lips. They were nice and meety, perfect for sucking and licking. My plan was to get on my knees on the floor and to start licking her pussy and jack off until I get a boner. Eating pussy is my favorite, this has to work. I begin by laying flat my whole tongue on her vagina so I can feel her full wet pussy and she can feel the warmness of my tongue. Her gasps and moans indicate to me that she needs more pleasure. I proceed to make love to her clitoris and kiss it passionately as if I’m kissing her lips. I run my tongue in and around her pussy lips stopping only for a short, tongue vibrating session on her clit. I kiss and pull her vulva with my lips, eagerly anticipating when is the right time to tongue fuck her pussy. Throughout this whole time one of my hand is constantly playing with her breast while I’m wacking off with the other one trying to encourage my penis to get out of his nervous funk. As I’m trying to pleasure my woman, the constant thoughts of why I’m not getting a boner are constantly haunting me which makes things even worse for my poor, nervous, little penis. Im at about half chub now, maybe it’s time. Once I’m inside her, the warmness of her pussy will make me even harder, right? She’s ready to take me, she begs me to give her my 3/4 chub which at this point I’m trying to play off as a massive rager. I’m sure it didn’t work, but she never mentioned anything. At this point, all the awesome fantasies we discussed and wanted to do are thrown out the window. I’m just trying to salvage the situation as much as possible without embarrassing myself too much with the first milf I’ve ever been with. She pulls up her legs and puts them on my shoulders. I slide slowly inside her and feel how every nerv on my dick is doing overtime. Her warm, juicy pussy was too much for my little trooper. I immediately came inside her in what must have been less than a minute. I could sense the disappointment in her tone as she gasped if I was finished. This was a disaster. This did not go perfect at all.

The next ten seconds in which I planned my next move, felt like an hour. I had to save face somehow. There was only one thing I could do. I was going to use all my cunnilungus skills to give her the best tongue orgasm possible. I cheekily thanked her and gave her a few passionate kisses before I made my way down to her beautiful, still wet pussy. I started twisting my tongue like a hurricane on her clit and slowly introduced my fingers one by one. With my fingers circling around in her pussy and my tongue doing it’s thing on her clit and juicy lips, I didn’t take long for her to sploosh all over my face.

“I’m going to squirt!”

She didn’t… she did however soak my face with her sweet pussy juices. We fooled around for a little longer and we both went our ways. We didn’t really have sex again that evening like we planned to. All things considered, I’m glad I at least gave her an orgasm with all the erectile problems I was having. It was my only saving grace. As I was driving back contemplating why my penis betrayed me, I could still taste and smell her Pussy juices all over my face, which annoyingly started giving me a boner. I thought I’m just cursed, it wasn’t meant to be. She would never call again, she surely wanted someone more experienced and less nervous to fuck her the way she desires.

“I had a great time today! Thank you for being such a gentleman. I hope you liked me enough to repeat again soon.”

I was as surprised as you are when I read the message she sent me that same night. She didn’t seem to care much about my poor performance. She was more worried that I didn’t perform well because I didn’t like her, which was not the case. Goes to show how our insecurities can blind our judgement sometimes. We never got to explore our fantasies that day. But there’s a time and place for everything.

Thank you for reading, everyone. This is my first story ( 99% true ). I hope you enjoy. I never really told anyone about the exact events of this and it’s nice to share it with someone, like you my fellow pervy strangers. If you enjoyed this story and are curious If my special lady friend and I ever got to explore our uninhibited fantasies together let me know and I will make a part 2 discussing the events of our second meeting and beyond.

Source: reddit.com/r/gonewildstories/comments/bseien/mf_shy_college_graduate_and_his_first_milf