“Sure Thing” Network: Part 1

The girls network, and Fifty shades of virginity.

Based on a post by reader4175. Listen to the Podcast on My First Time.

Kaitlin.

Being nearly a year older, I developed physically and mentally at a pace the other guys couldn’t keep. It helped me get the girls’ attention and interest.

Sadly, my academic development was nothing to boast about.

Kaitlin was a sporty little blonde, with tiny tits, a tight ass, brown eyes, a great smile and perfect teeth. I'm not sure what really even made me interested in her, other than her smile. It was always there and kind of infectious. She was different from most of the girls, because she would take time to talk to anyone. It didn't matter who you were, what you did or what you looked like, she would still talk to you.

I did not think that I had a chance in hell with her, but I didn't think that I had a chance in hell with any girl right about then.

She was right in front of me one day leaving class and I had a question about an assignment, but the teacher was busy, so I asked Kaitlin.

She turned, looked up at me and said "Come over to my house after school and I will help you with it."

Thàt was not the answer that I was expecting, but I was not going to turn down her invitation.

We both had our own cars, so I met her in the parking lot after school. I followed her home and she invited me into her empty house. We sat down at her kitchen table and she wanted to get right to work. I was having a hard time doing anything. I was really just staring at her and wondering where this might go. She noticed that I was not paying attention, looked up and asked me what was going on. All I could say was that I usually took a bit of a break when I got home from school before I started my homework.

She asked me if I wanted something to drink,

 I said “yes”, and then watched her walk away.

She told me; “come to the fridge and pick what you want.”

 I was looking over her shoulder and all I really wanted was her. I said that I would like a Mountain Dew so she handed one to me. I started back towards the table, and she said “why don't we go into the living room.”

I sat down on the couch and she sat down right next to me. I really was not expecting that, so I turned to look at her and she just smiled. I took that as a good sign and put my arm around her. She just snuggled in and put her head in my chest.

I really didn't know what I was doing, but I lifted her chin with my hand and leaned down to kiss her. She didn't say a word and kissed me back. I scooped her up into my lap and slid my hand up her shirt as I continued to kiss her. Again she didn't try to stop me. I squeezed her tits and tweaked her nipples for a few minutes while I kept kissing her. When I tried to move my hand from under her shirt to the waistband of her pants, she pulled away and said “that's enough, we are done.”

I must have looked disappointed, because she said “it's not your fault, this is only as far as I am willing to go.”

 I ask “so what now?”

 She said; “we could go back to our homework or you could take matters into your own hands.”

 I asked what that was supposed to mean and she said that she wouldn't help me, but if I wanted to finish myself, she would take off her shirt, sit in the chair across from me and watch.

I was hard as a rock and she could tell. I asked her to get me a towel. She came back with the towel in one hand and her shirt and bra in the other. I stood up, peeled off my shirt and dropped my pants.

Her eyes lit up, so I dropped my boxers and sat back down. She took her seat and started to play with her own nipples. When I started in on myself, she licked her lips and slid one hand down her pants. I really got going watching her do her own thing. When I was getting close, I spread the towel over my stomach and chest. She gave me a funny look and I just said “wait.”

When I finally came, I shot three big ropes up onto my chest, almost to my face. She must have really enjoyed watching me, because just as I finished, she shuddered and came. I folded up the towel, but then asked her if she wanted a taste. She nodded her head and said “yes.”

 I stood up, walked over to her and jerked the last few drops into her mouth. She played with it for a few seconds and then swallowed it.

We both got dressed and she asked me if I still wanted to do that homework. I told her that I thought I would be able to concentrate now.

 She laughed and said “let's go do it.”

I had not performed for a girl before, but she must have been impressed and told her friends about it, because the next day in class she told me; “Meredith would be interested in helping you you’re your homework tomorrow night.”

Kaitlin and I never got together again, but she would always give me the sweetest smile and occasionally direct me to another girl that she thought would like me.

Meredith.

Meredith had a different look than most of the girls at my school. She was a dark haired beauty, with dark eyes, pale white skin and a toned dancer's body. She could have easily played Wednesday Adams.

It was not the next day as Kaitlin had implied, but one day at lunch, Meredith sat down across from me and said, “I heard that you could use some help with your homework.”

 I asked her what Kaitlin had said. Her reply was; “You are a sure thing.”

I asked her what she had in mind. She said that her parents would be out Friday night and that she would like me to join her in the hot tub for an adventure. I had not been in a hot tub before, let alone in a hot tub with a girl, so I showed up to her house Friday night in jeans and a T-shirt with my swimming trunks in my hand. She said “you really don't need those, but if you would be more comfortable, we can start with swimsuits on.”

 I said that I thought that was best.

She pouted a little and I said “don't worry, we will get to where you want to go.”

She just said “Goody,” and showed me the bathroom. When I came out, she was waiting in a tiny black bikini.

She led me outside to the hot tub and we climbed in. I sat down and as soon as I was settled she sat down on my lap facing me. She then said “we can do this the fast way or the slow way, but either way we are both going to cum.”

 I told her; “ I’m not in a hurry, so we can take it slow.”

 She said; “that would work for me.” and then leaned in to kiss me.

My hands had been resting on her hips since she sat down, but they crept up to her ribs, and then her perky little tits, as we continued to kiss.

She broke our kiss and told me; “take my bikini top off,” which I happily did.

 As soon as it was off, she held up one of her own tits and said “suck it.”

 I didn't hesitate and latched right on. She started grinding on my lap and then whispered in my ear "I'm not going to fuck you, but you're going to cum really hard."

I didn't know what she had in mind but I liked the sound of it.

Meredith stood up, stripped her bikini bottom off and sat back down in my lap facing away from me. She guided my left hand to her tits and my right hand down to her pussy. I didn't really know what I was doing, but she put her hand on top of mine and guided my fingers to where she wanted them. Once I got going, she tipped her head back onto my shoulder and started moaning in my ear. I must have been doing it right because she shuttered and stiffened in my lap. When she finally relaxed from her orgasm, she turned and kissed me and then told me; “ it’s your turn.”

She told me; “stand up and take off your trunks.”

 I did and then she had me sit down in front of her. She pulled me into her with her left arm and reached down to stroke my cock with her right hand. I hadn't gotten a hand job from a girl yet, let alone a reach around under water. I leaned back into her and just let her do her thing. When she started talking dirty into my ear I knew I wasn't going to last very much longer.

I told her that I was going to cum and she told me; ”stand up and shoot it into my mouth.”

 I just wanted her to finish me, but I wasn't going to pass up this chance, so I stood up in front of her and started jerking myself off. She sat up and opened her mouth. I leaned in and put my hand on the edge of the tub next to her. I got as close to her mouth as I could and fired shot after shot onto her waiting tongue. She took it all and swallowed it down. Just as I started to back away, she leaned forward and sucked the last drops off the head of my cock. It wasn't a blowjob, but I now knew I wanted one in the worst way. I sat down next to her and pulled her in tight.

She told me not to get attached, because this wasn't likely to happen again anytime soon, but she would direct me to a few friends who would be interested in helping me with my homework.

 I leaned in to kiss her again and she gave me a sideways look. I said that I didn't care and pulled her up onto my lap facing me. When I started to get hard again underneath her, she hopped off and said “that's not going to happen, but the other girls will love you.”

Sara.

Meredith must have spread the word, because I started to get smiles from a lot of girls that didn't usually even look my way. I was starting to wonder if there was something wrong until Sara sat down next to me in class and asked me if I needed help with my homework.

I said; “I wouldn't mind studying with her.” In truth, I had had my eye on her for years.

Sara was my type, just over five foot tall, a big smile, nice teeth, brown eyes, dirty blonde hair, glasses and some of the biggest tits in our class. Those boobs had drawn me to her since they first popped out.

I asked her what day she had in mind and she said “Friday would really be the best, because my mom has an evening shift.”

Friday rolled around and Sara was waiting at the door for me. We headed out to my car and waited for the parking lot to clear out. We headed for her house down by the lake. It wasn't very big and there wasn't much in the refrigerator. I suggested that we go back out to the corner store for some refreshments. She gave me a sideways look and I said that I needed some fuel, before we would be doing any homework. She turned around and we headed back out the door.

I don't really remember what we picked up for food, but I know that I got a bottle of Mountain Dew. We got back to her house and sat down for a few minutes. Apparently Meredith had talked up the fingering skills that I didn't know I had. Sara said that she wanted me to do for her what I had done for Meredith in the hot tub except that she did not have a hot tub.

I really didn't know what the hell I was doing, so I suggested that were go to her room and I started by giving her a massage. She was a little shy and turned her back to me when she started to get undressed. I peeled my shirt off and waited for her. She turned to face me with her hands covering her tits and just a small patch of hair between her legs. I asked her if she had any oil or lotion and she reached for a bottle, showing me one pointy nipple. I told her; “lay down on your belly and I will start on your back.”

 I started at her neck and worked my way down to her calves spending a little extra time on her ass. I really wasn't interested in feet, so I stopped there.

She rolled over with half lidded eyes and asked me to do the front. I started at her shoulders working on her arms and spending a lot of time on her tits before work my way down to her legs and skipping over her pussy. I moved back up and just kneaded her mound with the palm of my hand. When she started to squirm, I knew it was time to go a little farther. She had a chair near by so I sat down and told her; “come sit in my lap.”

 She sat up slowly and took some unsteady steps over to me. I cradled her back with my left arm and started to work my fingers into her with my right hand. I could only get my middle finger inside of her, so I started working it in and out. I slipped my finger out and split her lips so I could find her clit. I put my thumb on it and then slid my finger back inside her. Then I started working both my thumb and my finger at the same time. I turned my head towards her and could not resist sucking on her nipples. I got a good rhythm going and locked onto one of her nipples. It didn't take long and she shuttered and came.

I carried her over and laid her in her bed. I started to get undressed and she asked me what I was doing. I said “it's my turn now.”

 She said; “I’m not very good at hand jobs.”

 I said “that’s okay; I had something else in mind.”

 She got a concerned look on her face and I said “don't worry, I am going to use your tits.”

 She looked relieved and confused all at the same time. I picked up the bottle of oil and straddled her chest. I oiled up her tits and laid my cock between them. I held her tits together while thumbing her nipples and started to fuck them.

When I really got going, my head started to pop out the top. She looked down and stuck out her tongue. I wasn't going to make it inside her mouth, but if she kept it open, she was going to get part of my load. I sped up and started to bump the head of my cock on the tip of her tongue. That was just the added stimulation that I needed to finish and I shot three good ropes at her face. The first one went in her mouth and the other two hit her chin and pooled on her neck.

She must have swallowed the first shot because she licked her lips and said “thank you.”

 I asked her what she wanted to clean up with and she said “don't worry about it,” as she smeared my cum all over her chest.

I was done, although I probably could have gone another round. I asked her if she wanted anything else and she said “no, but you could join me in the shower if you want to.”

 Why not, I would love to wash those tits. I spent a lot more time washing her than she did me, but she gave my balls a nice fondle and stroked my cock a little. We dried off and got dressed. She gave me a nice kiss and said “see you in class on Monday.”

Carolyn.

Sarah must have talked to Carolyn because she sat down next to me at lunch one day and said if you give me a ride home today, I will help you with your homework. I didn't know what she had in mind, but I was game for just about anything.

Carolyn was the smartest girl I knew and I think I was always drawn to her because of that, but she did have a tight little body with an amazing ass. She has blue eyes and auburn hair that she kept just below her ears. She didn't exactly graduate a year early, but she finished her senior year at the local community college.

Carolyn was waiting for me near the main entrance after the bell rang. I was never in a big rush to leave the parking lot, because it was always a madhouse and I had almost been rear-ended a few times in the bumper to bumper line on the driveway. My stereo was shit, but we sat there listening to some music in my car until the parking lot cleared out. She lived really close to school, so a few minutes meant nothing.

We got to her house and she said today is the best day because everyone else is out. Word must have gotten around because she led me to the kitchen and handed me a Mountain Dew and then offered me a sandwich. I accepted and she got right to work making it. She didn't make anything for herself, but just sat there and watched me eat. When I was done, I looked up and asked her what she had in mind. She said that it was time for her afternoon snack and that we should move to the living room.

She told me; “get undressed and sit down,” as she removed her shirt and bra.

She knelt in front of me and started rubbing my legs before playing with my balls and starting to stroke my cock. It didn't take long and I was rock hard. She leaned in and started licking up and down my shaft. Then she sucked the head of my cock into her mouth and swirled her tongue around the top of it. I knew she got a little bit of precum, but she didn't care. When she started bobbing up and down I reached out to put my hand on her head.

She pulled off and told me to put my hands down. I would get a chance to use them later. She started bobbing again and before too long, she was taking everything that I had. She grabbed my balls and started fucking her face with my cock. I couldn't hold back and shot my load into her mouth. She gulped it down and kept on sucking until I went soft. She looked up, licked her lips and said I want a massage. I said you're going to have to give me a few minutes to recover. She scampered off to the kitchen and brought me another Mountain Dew.

When I finished that, I said let's go. She gathered up our clothes and led me to her room. She stripped off her jeans and panties and showed me a bald little pussy. She handed me a bottle of oil and I proceeded to give her the same treatment that I gave Sara. When I got to her pussy she told me that she wanted me to finish her while she was laying down. I decided to lay down next to her for a better angle and more access. I started rubbing my finger up and down her slit until her lips parted and I could work my way in to find her clit.

When I started rubbing circles around it, she started to squirm, so I replaced my finger with my thumb and started working my finger into her. I got one in and it felt like there was room for a second. When I got that one in, she just shivered. I started working both my finger and my thumb, then I leaned in to suck on a nipple. Her tits were nowhere as big as Sara's, but they were perky. I kept up the same rhythm until she shuttered and came with a little squirt.

I was hard again and she reached down to grab my cock. She got her bottle of oil and lubed me up. She used both hands on my cock and balls and just kept working up and down, corkscrewing and swirling on the head of my cock. When I came, it wasn't as much as the first time, but she bent down and slurped it all up. I must have passed out because she was sitting up next to me smacking my cheek and telling me that it was time for me to leave. I got up and got dressed and she took me to the door where she kissed my cheek and told me to expect to hear from her again.

Carrie-Ann.

When wrestling season rolled around, we got a surprise. My buddy's older sister Carrie-Ann decided that she was going to wrestle. I didn't think much of it because I was a heavy weight and she was around 160, but I was wrong. All of the guys in her weight class refused to wrestle with her. She wasn't the prettiest girl, but what the hell, if she could wrestle with us, she would do better at her own weight.

Well, she didn't do all that well with us, because I was usually riding her ass and when we were standing up, I had her by her wrists so she couldn't move. We knocked 20 pounds off of her and she wore my fingerprints as bruises around her wrists for a month after the season ended. I didn't mind wrestling with her on the mat, but I wanted to take it to my bed.

We had a match the next night and everyone was happy to have an afternoon off. Because I had been spending so much time with Carrie-Ann, I thought nothing of asking her what she was going to be doing. She said; “I have some homework to do.”

 Without really thinking about it I asked; “Could you come over to my house and help me with an English assignment.”

 She said; “I had heard about helping you with homework,” and told me that I had better be ready for everything.

The next day after school we headed for my house. She had driven herself to school so she followed me home. We headed inside, I dropped my bag and headed for the kitchen. I rummaged around for a snack and drinks. She was just as hungry as I was.

Carrie-Ann wasn't the perfect girl, but I liked her attitude. She had worked some weight off, but she was still thick. She had long brown hair, but she had dreadlocked it for the season. She had bright brown eyes and a constant smile.

We finished up in the kitchen and headed for my bedroom. We had not seen each other naked, but our hands had been everywhere, so without even thinking about it, we both just started getting undressed. We eye each other up and she said "You're going to let me be on top today."

I grabbed her wrists and asked her if she was ready to wrestle for it.

 She said "No, you're just going to lay down and take it."

I was game for whatever she wanted, and I lay down on my bed. She stood up over me on the bed and just said eat it as she dropped her pussy onto my face. I didn't know what I was doing, but I just started licking everything until I got my tongue inside and then she told me; “suck my clit.”

 I was already rock hard and sucked on her until she yelped and told me; “go easy.”

I pushed her back and told her that this wasn't fair. She told me that I was never fair at practice. I said “how about you turn around and work on me while I work on you.”

She put her hands on my chest, spun herself around and backed her pussy up to my face. She didn't dive right in to blow me, but she started playing with my balls and gently stroking my cock. I got back to her pussy and from this angle, I was able to spread her open with my hands and used my tongue on her clit. When she started to buck her hips, I drove one finger from each hand into her and latched down hard on her clit. She screamed and locked up pinning my hands between her legs. When she loosened up, she rolled off of me and told me that she had won that round.

I said that she could look at it that way if she wanted to, but I was the one that made her cum. She said “well then, it is my turn to make you cum.”

 I told her to give it her best shot. What I didn't tell her was that I had taken care of myself that morning so that I would last longer with her. She started blowing me, but it was nothing like Carolyn had done, so I was a little disappointed. She had been down there for a while when she looked up at me and asked me what was taking so long. I said “if you want to make me cum, you're going to have to go for a ride.”

Her eyes got wide and I reached over to grab a condom that I had stashed next to my bed the day before.

 I tossed it to her and told her; “climb on if you want to beat me.”

 She didn't hesitate, rolled it on and straddled me. I never expected that it would go this far, but why the hell not. She lined me up and lowered herself down. When she was fully seated, my jaw dropped open and she gave me a strange look and then said “is this your first time?”

 I nodded my head and she said; “you asshole, if I had known that, I would have made it better.”

To be continued in part 2. Based on a post by reader4175, for Literotica.