Been a long-time reader of GWS and I’ve been in a bit of a dry spell recently. I’ve decided it’s time to give back. [Skip past the break for the good stuff!]
I didn’t have a whole lot of self confidence until very recently. About 2 years ago, I lost around 45 pounds over the course of 3 months on a keto diet. I’ve done a great job of keeping it off, and it’s done wonders for my dating life. I had a few opportunities for relationships in the past, but I never took it to the next level until last June, just before my 26th birthday. I’m a 5’8″ slim guy with a very angular face, brown hair, and blue eyes. My friends would describe me as nearing hipster fashion, but not quite. I have a 6″ dick that’s a little thicker than average.
I was poking around on various online dating apps, but I didn’t really ever make it past the 3rd or 4th date. I also didn’t really know when to escalate things to the sleeping over phase until this happened. Usually, I’m the first to message a girl. I was pleasantly surprised when my PoF inbox had a message from a bombshell. We’ll call her Monica.
Monica is 21 years old, 5’5″, and is the spitting image of Jennette McCurdy but with straight bright blonde hair. She has a killer body and is probably a little curvier than Jennette McCurdy, but not much. She is either a 36C or 34D and has an ass that just doesn’t quit.
“You’re so cute!” is all the message said. I’ve been described as “cute” by a lot of girls and it used to frustrate me to no end. I’ve since learned to accept it as a compliment. At the time, it irked me a bit. I responded, “I’ll pretend that by ‘so cute’ you meant, ‘a sexy beast’.” and followed up with my favorite ice breaker question: “What’s at the top of your bucket list?”. She answered by telling me she really wants to hold hands with an otter. We chatted for a good while, and the conversation was great. I asked her out to a pub downtown, and we made plans for that weekend. We met up and had a couple of beers. She was even more gorgeous than her pictures made her out to be. She wore a blue dress that accentuated all of her curves, and her smile melted me. The chemistry was clearly there, but she turned her head away from me when we hugged goodbye, denying any attempt at a kiss.
She was out of town the next week on a beach trip, and I had plans to go over a coworkers’ parents’ lake house the following weekend. It’s rare that I have a first date and can successfully wait that long for a second, but sometimes things work out well! We texted a lot over that week, always seeming to have something interesting to talk about. We flirted a little but neither of us directly brought up sex. She did send me a couple midriff pictures of a new bruise she acquired on her trip, both sexy as hell.
That weekend, while I was having stupid arguments with coworkers over beer in the hot tub, she called me. We talked for a couple of hours. Before hanging up, I decided to plan our next date. I gave a few suggestions and she followed up with “I just want to hang out with you. How about we just watch some Netflix and chill?” I laughed that last part off, thinking she was just joking, and she followed up with a “Seriously. Wine and Netflix sound great after this beach trip.” I decided on the spot that I was going to do everything in my power to fuck this girl’s brains out. The plans were made.
The following Saturday, she came over. I had a cheese and crackers platter, some dark chocolate, and a nice bottle of merlot sitting on the counter waiting for her. She was dressed much more casually than our first date. She was in a t-shirt and some jeans, and they suited her just as well as the dress did. The jeans accentuated her curvy ass, and I was immediately hard. We watched a movie, had a few beers, and finished off the bottle of wine. We were both pretty tipsy, but I was probably a little worse off than her. I had tried to pull her close and kiss her a couple of times, but she had laughed at me and kept her teasing distance.
Finally, I brought up the fact that the movie was almost over, we’d both had a ton to drink, and she still hadn’t given in to the kissing. She fake-pouted and gave me a “Fine. I /guess/ we can kiss now.” We made out for an excruciatingly long hour, starting out with light kisses, both of us teasing by pulling away.
————————————–
[The good stuff:]
She kept looking into my eyes with this sexy quizzical look. Her bright blue eyes had a drunken twinkle in them that just oozed sex appeal. After a good bit of light touching, I decided to try to apply some of the escalation techniques I’d read about. I gently lifted both of our shirts, pressing our stomachs together as we kissed.
She immediately kissed me more fully, with deep heady desire on her breath. I touched the small of her back and slowly moved my hand down to her waistband. I slid my hand down into her panties and grabbed her ass. She responded by kissing me with a lot of tongue. My finger made its way down her ass crack.
Her panties and ass were completely soaked. At first I thought it was sweat, but it was sticky. My finger made its way further down towards the source of the mess. Her pussy was warm, wet, and inviting. I pushed my middle finger inside from behind and was rewarded with a long and deep moan into my mouth.
Monica pulled back from our kiss and gave me that quizzical look. I recognized it now for what it was: fuck me eyes. I rubbed her a good while, attempting to pleasure her clit, but it was difficult from behind with her tight pants on. I went to take her pants off, but she suggested we move to my bedroom.
As soon as we got to my bed, our clothes were off in a furious whir. She was incredibly sexy and looked even better without clothes. Her breasts were incredibly perky for their large size, and they looked perfect on her frame. Her beautiful freshly shaven pussy had large pouty outer lips with inner labia that protrude out just a bit when she is horny. Her panties were sopping wet. “My god you’re wet”, I exclaimed. She responded with a smirk and a “duh” look. I pushed her onto the bed and kissed her hard. I kissed down her neck and towards her tits, making sure to take each nipple into my mouth on the way down. I kissed her flat stomach and made my way towards her completely shaven pussy. After kissing her thighs for a minute or two, I gave her mound a long lick from top to bottom.
She smelled and tasted like clean sweat and passion. It’s hard to describe any other way. She did not have a strong smell or taste at all. She is the only vegetarian I have been with, so that might explain why. I grabbed a condom from my nightstand and put it on. I decided it was probably a good idea to let her know this was my first time. “We don’t have to do this so soon if you don’t want to rush it.”, she said sweetly. I responded by rubbing my dick on her mound and replying “I want this so badly.”. She reached down and put me in. I began fucking her. Her moans were deep and full, full of desire.
I didn’t feel a whole lot through the condom and drunkenness, but I was still hard as a rock. After fucking in missionary for a while, I let her know that I wasn’t so sure I’d be able to cum in my drunken state with a condom. She told me “We can try again in the morning.” and started kissing me as we fucked. After a little longer in this position, my cognitive thought was overcome by horniness. I wanted to fuck her raw. I asked her if she was on birth control. She told me she had an IUD. I laughed and mentioned that I’ve heard you can feel the strings with your finger. She giggled and said she hasn’t before, but I can try. I fingered her a while and can say that yes, you can indeed feel IUD strings with your finger (and your dick sometimes, which isn’t always so great).
I asked her if she’s had an STD test recently, and she quickly explained that she had a very recent one. In a moment that luckily didn’t turn out to be a mistake, I pulled the condom off and rubbed my dick across her slit. She rolled over and propped her ass up in the air. The sight made me somehow even hornier. She rubbed her perfectly round ass against my dick and then reached back and put me inside. (Please don’t do this unless you’ve verified yourself that she is clean by looking at her paperwork. I lucked out, but I’ll never ever do this again.)
The feeling was incredible. I’d felt a fleshlight before on several occasions, but this blew it out of the water. She was silky and almost uncomfortably warm inside. She pushed her ass back against me, bringing me a little deeper. I fucked her brains out, grabbing and slapping her ass. I got a little adventurous and pressed my thumb against her white little asshole, and instead of resisting, she just moaned louder. “You like that?”, I asked. “Yeah… I do.” she replied. I didn’t press my luck much more than that on the first night, but I did continue fucking her brains out. Her moans were loud now, and I’m sure my neighbors could hear, but I didn’t care. I could feel her pussy spasming around me. I couldn’t take it any more, so I pulled out and came all across her back. I later learned she’d been about to cum herself, but I definitely helped her out on that front more than enough during the relationship that followed. We cleaned up and went to bed.
The next morning was father’s day, and we indeed did try again, regardless of the fact that I’d blown my load the night before. I woke up with her back snuggled against me, hard as a diamond pressing against her ass. The morning sex was even more fantastic than the previous night’s. We both weren’t drunk, and her dirty talk was fantastic. Inbetween her characteristic deep heady moans, she praised me, calling me sexy and telling me I have a perfect dick. We fucked in more positions in a single session than I ever have since. When I came, I accidentally got some on her shirt. Even though I didn’t do it on purpose, I took a devilish pleasure in knowing that she would be borrowing one of my shirts that morning to go meet her father, since the one she’d planned on wearing had my cum on it. My just-desserts, however, were that I had to go spend time with my father and grandfather while completely hungover and in a post-fuckfest state of exhaustion.
Monica and I dated for a couple of months after that. I have plenty of good stories about our sex life during that time, but we both realized we weren’t a good fit. She is a good deal more wild than I am, and it made me uncomfortable at times while stressing her out and making her feel like she had to be more reserved than usual.
Please let me know if you want more stories about Monica. I only have a couple of stories that don’t involve her, but I’d be happy to talk about those too. A little feedback via PM would also be excellent.
Source: reddit.com/r/gonewildstories/comments/7mfmpe/losing_my_virginity_to_jennette_mccurdys_long
Good story &, well written
Monica sounds like an amazing girl for a first time