Kate Vs Samantha Vs Leah

VS. #1

I have been on alot of blind dates that I set up online. Sometimes I met two nice girls at the same time and dated them both for a while before I decided on one of them. Sometimes I picked neither of them. Sometimes they both ended up dumping me! I thought it might be an interesting series. These are absolutely true stories. I'm sorry if you think it could have been hotter, but this is how it actually happened. Here is the first installment.

Kate vs. Samantha vs. Leah

My first try at internet dating did not go well. I set up a date at Old Chicago. I went at the decided upon time and ordered a coke. After 15 minutes she still wasn't there. After 30 minutes she still wasn't there. I didn't have her number, so I couldn't call or text. I told the bartender what was going on so he didn't think I'm the kind of guy that drinks a coke alone at a bar. After 45 minutes, I gathered she wasn't coming. The bartender said the coke was on the house, so at least I got a free Coke. When I got home, I checked my email and she had cancelled, like, 15 minutes before we were supposed to meet. I was never going to lose my virginity at this rate. I was 22 and had never really tried dating before this. Every time I tried to pick up a girl, she had a boyfriend. Hopefully, girls on dating sites would at least be single! Eventually, I hoped, I would find a girl that would show up for the date.

I started talking to two women. One was 35 and was in the intimate encounters section. The other was 19 and also in the intimate encounters section. I didn't get a picture of either of them. The 19 year old only emailed a short message every few days. I was not getting anywhere fast with her but at least she kept writing back. After only 3 emails back and forth, the 35 year old agreed to come to my apartment for dinner. That was easy! She was coming over for a Friday dinner date. I was cooking my famous Chicken Pesto Mozzarella. I had on my white dress pants and a black button up shirt and was looking good!

I had the chicken nearly ready and was making a salad when my phone rang. It was the 'doorbell'. I buzzed up Kate. She had brought a bottle of wine. Luckily, she had a bottle opener. She had a rather plain face with shoulder length blond hair. She had on white dress pants, a light blue sleeveless top and over that, a white button up tied in a knot at the bottom. She was about 5'6" and had a curvy body. I usually like thin girls, but Kate turned me on. She was really nice to talk to. She had lots of interesting things to say about alcohol, restaurants and all sorts of things. She was very smiley. Maybe she was excited a younger guy was into her.

She liked my cooking and the wine she brought was great! I was feeling pretty buzzed. After we finished eating, we were clearing the table and putting the dishes in the dishwasher. I got a really good look down her shirt as she put a couple plates on the bottom rack. She had big white tits in a black bra. They were probably a C cup. I really hoped I would get a better look later.

"So, I have to tell you, I have a boyfriend that I live with, but we have an open relationship. He knows I'm here and he's fine with it." Kate told me.

"Oh, OK." was all I could say.

"When did you lose your virginity?" she asked.

"I hope I'm about to." I replied, hoping she would not be turned off by that admission.

"Oh, well this is quite an honor." she said. "I hope you think I'm sexy. You want to lose your virginity to someone really hot."

"You're very sexy. I was really hoping this would happen when you walked in the door." I told her, "And you're a really awesome person too."

This made her smile and she moved in for the kiss. I stuck my tongue in her mouth and moved it all around. I used some tricks on her that I had looked up on the internet. She hung with it for a while and then recoiled and gave me a look. "Um, can you tell that was my first kiss?" I asked.

She gave me another big smile. "Yeah, you're using way too much tongue. Here, I'll show you. Just kiss my lips and don't open your mouth yet." I gave her slow kisses right on her lips. "Good, now you can open your mouth a little but no tongue yet." We kissed with an open mouth and put our arms around each other. It was everything I thought it would be. I felt so close to this person I just met.

"Are you ready? Let's go to the bedroom" she said. I didn't say anything. I just took her hand and walked quickly to the bedroom, "Do you want to undress me?"

"Yeah, I can't wait." I had given up playing it cool. She gave the impression of someone that wanted to instruct me in how to put my cock in her. It seemed there was no way to blow this.

"You take something of mine off and I'll take something of yours off." she said. We were standing right by the bed. I undid the knot on her button up and slipped it off her shoulders. Kate took my shirt up over my head and then ran her hands over my chest. I un-tucked her light blue shirt and then pulled it over her head. Now I had a good look at her lacy black bra and her pale white cleavage. She took off my belt with a flourish, ripping it out of my belt loops and tossed it on the floor. I fumbled with her bra for a couple seconds before she helped me and her bra fell softly to the brown bedroom carpet.

Neither of us said anything. It was not my first look at tits. I had been to a strip club. Kate's boobs were really nice. Big, round and white with average sized pink nipples, they sagged just as much as you would expect C cup boobs to sag. My hands instantly went to them. She could tell I was really enjoying playing with her tits. She had that charming smile all over her face. "You have nice breasts." I told her.

"Glad you like them. But I have more to show you." she said seductively. She unbuttoned her pants and took them down. She had smooth pale legs. She was not fat but not toned at all. The best part of her was definitely her tits. I took off my pants. I grabbed the waist band of her black lacy panties and took them down over her thighs and down to her feet. She was totally shaved.

"Can I lick it?" I asked.

"Yeah, if you want to." She laid back on the bed and spread her thighs. Her pussy was a pale pink with average sized lips. I grabbed her soft thighs and went to work with my tongue. I licked mostly up and down but I changed it up with circles too. I was afraid it would taste bad, but it tasted kind of like salt and vinegar, in a good way. "Mmmmm, that's good for your first time." She said. I had seen this in porn and had some idea what to do. I slipped off my boxers and got up to grab her boobs and kiss her smiling lips.

"Do you want to fuck me?" Kate asked.

"Oh my God, Yes." I said. I was nice and hard. She got off the bed and went for her pants pocket to fish out a condom.

"Here, let me roll it on you." she said as she tore open the packet. She rolled it on my dick like an expert and lay back down on the bed. I got between her legs and tried to guide my dick into her. By now, we were a minute past the initial excitement and we'd been screwing around with a condom, so I was only semi-erect. I stuck it in her wet slit and tried to get a rhythm. I couldn't feel much with the rubber on and not being very hard.

After a minute or so, she could tell I was having trouble. "Here, let's try this. Lay down." She took the condom off and took me into her mouth. Her warm, wet mouth brought me back to life. As soon as I was hard again, she straddled me and sat on my dick. I was fully erect and inside a woman. She pumped up and down on me.

"Tell me if you're going to cum." She said. Watching Kate's boobs bounce was mesmerizing. She had a cute belly button. I grabbed her sides and felt how warm her body was.

"Do you want to try on top again?" She asked.

"Yeah" She went for her pants pocket again and fished out another condom. Again, she rolled it on me and lay down on the bed. I could feel my cock shrinking. I slipped it in her and tried to pump but it felt like it was coming all the way out. It didn't feel like anything. I focused on her sexy body and thought about cumming on her flat belly or her big bouncy tits, but it wasn't working. After a while, I just kind of fell out. "Dang." was all I could say.

"We'll have to work on that." she said "but hey, you're not a virgin anymore!"

"Yeah, sorry I couldn't....finish the job." I said.

"Here, lick my pussy." she said as she flopped on her back. I licked her freshly fucked pussy like I was trying to win a prize. She rubbed her clit and started moaning and squirming. It wasn't even a minute before she let out a big moan and her body stiffened up. "Mmmmmm, that's good. Always help your partner finish. Sorry I'm out of condoms."

"That's OK, I had my chance." I said. I was kind of disappointed but that was by far the hottest thing that had ever happened to me and I had a good feeling I would see her again.

She started putting her clothes back on. "I hope I see you again, but if not, here's something to remember me by." she handed me her black lacy panties. "A fat chick's panties."

"Ha, no way. You're sexy." I said, taking them.

"You're sweet." She had finished putting on her clothes by now (minus her panties, which I was about to jack off with) She gave me a long kiss on the lips and was out the door.

Meanwhile, I had started talking with a new girl. Her names was Leah. She was 20 and went to a small college at a nearby town. I met her on the intimate encounters section too so I didn't think it would take much work to get into her pants. She had a picture but it was a far away shot so it was hard to see exactly what she looked like. We quickly set up a "date", if you can call coming over to my apartment with no plans for dinner or anything a date.

She came over on a Friday night at about 8. I opened the door and saw girl with a cute round face, about 5'7", with brown straight hair a little longer than shoulder length. She had on a T-shirt and jeans. She was kind of thick but had a nice figure. Leah had a little bit of a belly and a big but shapely ass. She had a small chest. I though overall she was pretty good looking. We sat on the couch together. I left the TV off.

"Can I get you a drink?" I asked, getting up.

"Yeah, what have you got?" Leah replied.

"I can make you a rum and coke or a gin and tonic. I also have some coronas." I answered.

"Oh, I've never had a gin and tonic." Leah said.

"OK, G and T it is. So have you met anyone on this site yet?" I asked.

"No, you're my first." she replied. "I just got out of a relationship. I was engaged but we broke it off." I wasn't sure if she'd want me to ask more so I just let her keep talking. "Have you ever done this before, I mean, have sex?"

"Just once and I'm not sure it counts. How many people have you had sex with?" I asked.

"I've only ever gone out with my ex-fiancé. We were waiting for marriage. It's kind of a Christian thing. So I don't think I've ever done anything that counts as sex. So, I was with this guy for 3 years and we never had sex, so I just want to do it now." I was a really curious exactly what she'd done with him, but wasn't sure I wanted to make her think about that. We talked for about an hour. She was so easy to talk to. I made her laugh alot but whenever I told a joke that fell flat, she would tell me, "You're funny..... looking" I respected that she didn't feel the need to fake laugh.

At the first long pause in the conversation, I leaned in and looked into her eyes. We both moved in for a long passionate kiss. She was a good kisser. We had our hands all over each other. We broke and smiled at each other. I took her hand and led her to the bedroom. I took off my shirt at the same time she took off her shirt. Then we took off our pants and I tumbled onto the bed on top of her. We kissed and felt up each other's body. She had nice tan smooth skin. She had the kind of body where you could tell she was active but didn't work out. She looked sexy though. I was excited for what was about to happen.

I unhooked her bra and a rolled up sock tumbled out, "Oh" I blurted out.

"Yeah, I have uneven breasts." then she dead-pan added, " That's the whole story." Her right breast was little more than a nipple. Her left breast was about a B cup.

Thinking quickly I said, "As long as I can squeeze them, it's all good." I took off my boxers and she took off her panties. She had a little patch of brown hair above her pussy. She had a plump little pubic mound and a thin lipped pinkish brown pussy. I rubbed it til it was super wet, while we were still kissing.

"Do you have condoms?" She asked. I ran over to the dresser and grabbed one. I put it on as quickly as I could and put my dick in her sopping wet pussy. I fucked her hard and made her belly jiggle. It kind of felt good. I couldn't feel much. She just closed her eyes and took it. She didn't really make any noise.

"Do you want to try doggie?" She asked.

"Sure. I've never done it before though." She got on all fours and I got behind her. I grabbed her ass. It was soft but shapely. She reached her hand back and guided me into her. I slammed my dick into her and watched her ass jiggle. She had a smooth tan back and I put my hands all over it. Then I put my hands on her soft belly. I had a nice rhythm but I didn't feel like I was anywhere close to cumming.

"Can I get on top? Leah asked.

"Of course." I said, but when I pulled out, I saw that I was pretty soft. She tried to sit on my cock but it was too soft to go in.

"Did you cum?" She asked.

"No, I think he's on his lunch break." I tried to joke.

"OK, Well let's just cuddle. That was nice. Thanks for helping me lose my virginity. I hope we can practice more." Leah said.

"Yeah, I'd love to. That was hot." I said.

"Do you want to be my boyfriend?" she asked.

I tried to think quickly, "Do we have to put a label on our relationship already?" I think it's against Intimate Encounter rules to ask that after the first encounter. I was probably lucky she let it go.

Anyway, I started instant messaging her every night. She had a handle that definitely backed up her story about previously being too Christian to have sex before marriage. I talked to Kate too. Kate told me that I should try to hook up with someone my own age, although she still selfishly hoped we could hook up again. She also told me she had a younger sister that she wanted to set me up with. Banging two sisters sounded hot!

Leah wanted to see me again the next weekend. I was going back home to my parents because it was my sister's birthday and we always got together for birthdays but I told her I could stop by Friday on my way home. I pulled up in front of her dorm and she came out to meet me. She was wearing jeans and a T-shirt again. We walked around campus holding hands and having a nice conversation. I told her I should get going or I'm going to get home super late. Then she smiled at me and asked if I wanted to see her dorm room. Yes, I definitely did.

We started kissing even before we got in her room. We tumbled onto her bed and I laid on top of her, kissing her sweet pink lips. "Let's keep our shirts on in case my roommate comes back." We took down our pants. She had such strong looking sexy thighs. We still had our pants around our ankles. I quickly put on a condom and put it on my hard cock. It slipped easily into her wet pussy. We were in a dorm and we were trying to be as quiet as possible. I was moving in and out of her slowly. "Can we get under the covers?" She asked. We tried to get under the covers as best we could and still keep fucking. Her pussy was super wet but didn't feel that tight. Then she said, "I'm sorry, I'm just really afraid my roommate is going to come back. She's going to be back any minute." So we pulled our pants back up and that's where it ended for that date.

I kept talking to Kate and Leah on messenger, but a few days later, the 19 year old told me that she wanted me to pick her up on her lunch break, fuck her and take her back to work. That sounded pretty weird to me, but I wasn't going to say no. I was pretty sure my relationship with her was going nowhere so this turn of events was a nice surprise. I told work I was taking the afternoon off.

She worked on Campus as a janitor, which is not a normal job for a 19 year old girl. She was wearing some kind of janitor's uniform - like beige coveralls. She had a short haircut and gave off a goth vibe or maybe a nerd vibe. It was hard to read her and she gave up practically nothing in talking to her online for a month. Our conversation was pretty much, "Are you Samantha." She nodded and I said, "Great, my car's this way."

"How far is your place?" is about the only thing she said on the way home.

"About 5 or 10 minutes, depending on traffic." I figured whatever was under those coveralls was going to be really good or really bad. I unlocked the door to the apartment and she took a quick look around. "I'm going to freshen up in the bathroom for just a minute." She said. I wasn't sure whether to take my clothes off or what to do. I took off shoes and socks. When she came back out of the bathroom, she was completely naked. She stood in my doorway and smirked at me. She was about 5'9", thin, pale, with about B cup tits. I was surprised she didn't have any tattoos or piercings (other than ears) that I could see. Samantha wasn't toned but she was nice and thin with a nice perky ass. I quickly took off my clothes and we started making out in front of the bed. I rubbed my hands up and down her body.

Then I pushed her on the bed and started licking the sweet slit between her legs. She had cute pink pussy lips and a tuft of black hair above her cunt. It tasted good but I noticed I was getting no response. I started to get self-conscious. This girl had a nice body and she was in the middle of a dirty job so she probably was actually very hot if she was dressed up for a night at the bars. Maybe she was disappointed with me? She didn't seem into this at all. Then I started thinking about Leah and how I probably shouldn't even be doing this. Still, Samantha was hot and I wanted to fuck her.

"OK, put on a condom and fuck me" she finally said. I looked down and my cock was not looking ready for that. I reached down and calling it semi-erect would be optimistic.

"Mmmmm, that's going to be a problem." I told her.

"Come on, I don't have much time." She didn't offer to lend a hand or suck it or anything. I tried to stroke myself but I was super self conscious now.

"OK, well, take me back to work." She commanded. This was so humiliating and I didn't get to have sex with the hot naked girl in my bedroom! We put our clothes on and I drove her back to campus. It was an even more awkward ride back. I'm not even sure we said, "Goodbye"

Obviously, there was a problem. I had always heard, you want to masturbate before a date so you wouldn't be prone to premature ejaculation. But that wasn't my problem. I had the opposite thing going on. I decided to try laying off whacking off for a few days before a date. I had another date with Leah on Thursday and decided to put my plan into action, but then disaster struck. OK, It wasn't that bad. But it totally de-railed our next date. I locked myself out of my apartment! It was after office hours so there was no way to get in until the next day. I was forced to call Leah and tell her I had to cancel and hope she wouldn't think I was blowing her off. Fortunately, she invited me to the Fall Carnival her college was having so at least we just postponed getting together. Someone finally let me in the building and I slept on the floor in front of my apartment until the morning came.

That Saturday, Leah met me on the campus green. She was wearing gym shorts and a T-shirt. "I have to help with the rock climbing wall or I would have dressed up a little more." she explained, "It's just for a half hour though." We walked around for a while and played a few of the games and had a great conversation once again. She was so funny and I could generally make her laugh too. I watched her help with the rock wall, which consisted of holding the other end of the climbing rope and ensuring if the climber fell, they wouldn't plunge to their death or anything like that. I enjoyed watching her in action. She would brace herself and in doing so, show off her legs. She had powerful, tan muscular legs, which was a huge turn on. Finally her shift was over. It was so busy I never got a chance to climb, which I was OK with.