Let me start off by saying, I’ve never had casual sex before. I got married young because of a religious background and was faithfully monogamous during my marriage. Now, however, I’m living a little. Dipping my toes in the water, if you will. To see a little (Or lot) of what I look like, check my post history.
To begin, I had an overnight trip out of town. Just one night, no time to really see any sights. The only fun possibility lay in time with a new friend back at my hotel. Not one to miss an opportunity in life, I posted on the local gone wild page to see if there was any interest. I got some bites. One couple wanted me to be a part of their quest to turn straight boys bi. Other couples were interested in some group fun. I was looking to dip my toes in the water however, not dive headfirst into the freaking amazon river. The winner for me was Nevani. She was young, had a pretty face, dark skin, and what I understand the kids say is a “thicc” booty. She was busty, and adventurous. On the night in question, I messaged her at 9:30 PM. Nevani responded and agreeably said she could be to my hotel in about an hour. She was just leaving a friend’s birthday. Perfect. This gave me time to finish my beer and salad.
Well, Nevani didn’t know this part, so if she reads this, it will be a surprise. But she messaged me to let me know she was 20 minutes away. In that moment, I, who haven’t worn a condom in 6 years, am confronted with the reality that I have none. I quickly pay my bar tab and run to the car to find the nearest gas station. I select out a condom brand that another redditor recommended as the best. After paying for it, the middle aged woman checking me out said, “have a safe night!” Without missing a beat, I quipped “that’s the idea!” and I ran out the door being chased by her cackles of belly laughter. I’m back at the bar at least a full five minutes before Nevani arrives. Crisis averted. She messages and asks me what I’m wearing so she can identify me. A Blue t-shirt and Khakis: a standard white guy outfit. Nevani tells me she is wearing a sweatshirt and leggings. Only a few minutes later, she walks up behind me says “hi” and gives me a bit of a side hug as I’m turning to see her for the first time.
Now Nevani is pretty tall for a woman, about 5’8” and solid throughout. The sweatshirt doesn’t give me an idea of what is underneath though. She has a pretty face and a kind demeanor. I ask if she wants a drink, she politely says no thank you and she’ll just take water. The bartender brings both of us waters and we begin chatting. I ask about her job, her family, whether she has kids, etc. She seems very shy in all her answers but seems to be enjoying my company. After about 7 or 8 minutes, I realize I have to do something. We’re sitting at a bar drinking water, this clearly can’t go on that long, not to mention the atrocious atmosphere of the establishment. But, as I’ve said before, I’m a complete rookie when it comes to this, so I just admit that. I lean over and say in an almost whisper, “So I’ve never done this before. What would you like to do next?” Nevani, in a kind voice, says “we can keep talking here, we can go back to your room, or we can go talk in your room.” Being the diplomat that I am, I split the difference. So back to the room we go to “talk.” Right. No one saw through that Mr. Lawyer. I ask if I can hold her hand on the walk to my room, she says yes and takes it in hers. She interlocks her fingers but does it one finger above what I am used to from my ex, the person I spent the last dozen years with. Ever tried folding your own hands, then folding them the other way so the opposite thumb comes out on top? Yeah, it was like that. Certainly not unpleasant, but it felt alien and foreign holding Nevani’s hand.
We get to my room and chat for a second about the room. We both kick off our shoes and climb on the bed. Approximately 2 feet between us. We chat for another 30 seconds and I comment on the space and ask if I can get right up next to her. She responds with of course, but adds that she knows I’m relatively new to this and so she didn’t want to pressure me into anything. Now let me tell you this my dear readers, I have a woman, sitting on my bed in my hotel room, who came because she liked what she saw in my online posts. I certainly didn’t feel any pressure. But still, it was sweet and thoughtful of her. I reassured her by pulling her legs across mine and running my hand up and down her leggings. I don’t think we had more than another 15 seconds of dialog when Nevani asks me “can I kiss you?” “Yes,” I reply. She puts her hand around the side of my face and pulls me in for a kiss. Now, she had big plump lips. I hadn’t noticed them visually before, but when she came in for the kiss, I was struck by how soft and plump those lips were. They were good lips to kiss and be kissed by. While we kissed, she climbed on top of me and begins grinding back and forth while kissing.
Next, she pulled off her sweater to reveal substantial cleavage overflowing from her bra. I leaned forward and began kissing her ample breasts. Quickly the bra came off revealing perfectly shaped nipples. I put my mouth on one, teasing it with my lips, nibbling it with my teeth. Nevani began softly moaning as I worshiped her tender nipples with abandon. She leaned back long enough for me to take my shirt off before I brought her back to me so I could continue adoring her incredible breasts.
Finally, I rolled her over on to her back to take charge and began intensely kissing her neck. She lay back, underneath me as I worked down her neck, shoulders, breasts, stomach, only briefly pausing to grab both sides of her leggings and peel them downward to reveal a pink thong. I began kissing on her thighs and slowly moving up. Making sure not to neglect either leg, I sought the ultimate prize, but not too quickly. I began kissing on the outside of her panties. I didn’t force her to wait long before sliding the panties down and leaving her completely naked before me. Nor did I make her wait long before diving back in. She smelled and tasted pungent. Not unpleasant, but certainly not sweet. Undeterred I kissed with fervor. Nevani lay back and began to writhe under my lips and tongue. Up and down, side to side, I kissed, licked and loved with all that I had. As she began to buck more urgently, I locked my lips around her entire hood and gently sucked, letting my tongue swirl like a tempest. She violently shook as the first orgasm rolled through her body. After her waves of pleasure subsided, I stood up and stripped my pants and boxers off. Rolling on my (recently purchased) condom, I ask if she’s ready for me. Getting only a nod in return, I climb on top and slide in. Gently and slowly first. Wrapping her arms around me, she clenched down tightly as we tryst together. We pick up the speed, matching the other’s writhing. Now fully in the throws, Nevani is moaning into me. If she’s faking it, she’s pretty damn convincing.
Continued in the comments-
Source: reddit.com/r/gonewildstories/comments/11ftj1f/the_rookie_32m_in_sacramento_with_a_redditor_22f