My freshman year

It all began my freshman year of high school. I was 14 and still a virgin to everything. That’s right, never kissed, or anything further. I’m sure you know what all that is. My name is Dan; I was average height and sort of an athletic build. Not one to be on the football team, but basketball always served me well.
It was the first day of high school and I had 8 classes, all with people I knew, but no real friends. I wasn’t the smartest but I was smart enough to be in 3 honors classes, and 1 regular. The school I came from is full of kids who think they’re from the hood. The school was about 75% black kids, 15% Mexican, 5% Chinese, 3% White, and 2% other. I didn’t have many friends but the ones I did have I’ve known and hung out with since kindergarten. One good friend of mine who I will tell you about in a different story is Andrew. We’ve lived across the street from each other for over 10 years and just met at the bus stop in middle school. Me and Andrew are both white by the way.
We hung out almost every night. There were rumors that he was gay/bi but I didn’t talk about it. (Will get into that later). In high school we took our separate paths and made new friends. He did anyway, I stayed with my group of dumbass smokers and skateboarders. After the first semester of freshman year, Andrew and myself had the same elective for the last semester. We caught up and apparently he had been taking drama.
I wasn’t really surprised but one day I stayed after school with him and he introduced me to a bunch of hot girls. I immediately thought he was scoring with them, but after I started going there more often I got to know them and they haven’t done anything with him. I wasn’t sure to be happy for myself or sad for him.
The 2 girls names were Ashley and Melissa. Ashley was short, about 5 foot, and had great tits and a big round ass. Melissa was much taller, around 5 foot, 9 or 10 inches. She didn’t have much tits but he ass was tight in the clothes she wore. As I hung out with them more often, Ashley didn’t seem at all interested in anybody, but Melissa was always teasing, if you know what I mean. They were both white as well.
Whenever we would hug to say goodbye, she would grab my ass, squeeze my man tits, ^_^ and sometimes give me a kiss on the cheek. The entire year I was confused if it was a sign or tease. Towards the end of the year when she would grab my ass, I would grab hers, and when she would squeeze my tits, I would squeeze hers, and would give her a kiss on the neck if she pecked me on the cheek.
That went on till finals came. We only had 1 final together so we spent a lot of time talking before it. I got her email address and home number. I was really surprised and even a little disappointed when she said she didn’t have a cell phone.
It was a really boring summer for me. However the start of the summer was sort of interesting. My birthday was on the 6th of July. So I turned 15 without a party, a family dinner, about 400$ in mail from family. Nothing compared to my brothers 18th birthday on the 12th of august. He got a car. At least I had a ride whenever I needed one.
But back to my birthday, a few days after the email back from Melissa included an invitation to her birthday party. By this time I had been talking with Ashley over the phone and had learned that they were lesbians. That’s right, lesbians. I had a crush, on a lesbian.
This boggled my mind for days but when her birthday came around I got my mom to drop me off at her house and they would take me up to Bear Mountain for the party. When I showed up I knocked on the door, her mothered answered and yelled down the hall that I was here. I walk down the hall and turn to their room, it being the only one open, and they were getting dressed.
I had a smirk on my face as I said “What were you two up to?” Melissa laughed and said nothing as she walked out the door. As Ashley started to walk out she whispered to me that she hasn’t told Melissa that she told me. I nodded and followed her down the hall, staring at her ass the whole way down.
So on the car ride up we all sat in the back, a cooler and blankets in the front. We talked and through the talk I learned that Melissa was bi, and Ashley was lesbian. That got my hopes up way too much. I was getting aroused the entire time but managed to hide my semi-erect penis from pointing up out of my shorts. We arrived at Bear Mountain and I let them get out first, so I had time to fold my dick up my shorts so my boner wouldn’t show.
I guess you could say Ashley was very protective and emotional. So when she found out that Melissa invited her x-boyfriend to the party, she wasn’t very happy. I’m not really sure what happened for a while at the party, Ashley strayed off to think alone, Melissa tried to enjoy herself but really couldn’t without Ashley. I just stood around in the background trying not to make a big deal of anything. I introduced myself to the rest of the people at the party.
They all seemed fun to hang around with but since I didn’t know any of them that well I just walked around trying to find where Ashley was. It was time to eat and Ashley still wasn’t back. We all tried calling her, but apparently Melissa already did and said that Ashley was on her way back. After about 15 minutes of standing around talking she showed up and we all ate hamburgers. After lunch Melissa wanted to go on a boat ride, and since it was just 2 per boat, Melissa surprisingly picked her x-boyfriend. I saw how depressed Ashley looked and offered to go with her. On our way down to the dock Ashley offered me some ice cream and I accepted, not thinking it would be a big deal. After I took a bite she did and told Melissa that she and I had just indirectly kissed. She didn’t even bother to respond but I let out a small laugh as we showed up to the dock.
As we set sail Ashley and I talked a lot about how she was the only one interested in keeping this relationship going. I learned that she had caught Melissa giving head to her x-boyfriend. I kept quiet, not knowing how to respond. Although I don’t remember her exact words, I know that Ashley vented to me that day, and I actually had decent advice to give her. After the boat ride she told Melissa that she told me about them. I could see that Melissa was mad but she wasn’t going to show it in front of the party guests. (As far as I remember they did not know about them).
On the ride home we were all wet and in our bathing suits. We had come into the car with towels around us but they came off to simply stop the seat from getting wet. About 10 minutes of looking out the window I felt a hand on my thigh. I simply smiled as I looked at Melissa and placed my hand on her thigh. Almost immediately I was nearly fully hard and I then turned to see Ashley asleep. As I was turned back Melissa had placed her other hand on my chest and had leaned in, putting her face about an inch from mine.
I wanted this so bad I couldn’t stop myself, knowing that she would be cheating on Ashley. I leaned in the rest of the way and kissed her. We began making out, I used the hand on her thigh to stroke up and down the inner side of her thigh, and the other rubbing her back. She did the same except she used the hand on my back to push me in more, bringing her breast to my chest.
I broke our kiss and whispered in her ear, “what about your mom?” She laughed and said that she doesn’t mind. I shrugged it off and leaned back in to kiss her. By now I had brought my hand from her back to her lower stomach, and from her thigh to her waist. As we continued making out I started massaging her breast with one hand through her wet bathing suit and massaged her upper crotch. She started breathing heavily and we broke the kiss.
She then took both my hands and brought them to her breast. She then began working on my pants as she saw the bulge. She tapped the tip of my cock through my bathing suit and said you’re next. Then she lied down, putting her wet legs on my shoulders. I pulled down her bathing suit and asked if she wanted to be licked or fingered. She responded, “Both”. I smiled as I leaned in and put one finger in my first pussy. I started licking around the lips as I fingered her with my index finger. She was simply breathing heavily so I added another finger and started going faster.
She let out soft moans and I moved my lips to her clit. She moaned more often but I told her to keep it quiet. I was about to put in my third finger wet her orgasm hit and her juices covered my fingers and filled my mouth. I smiled and said “How was that?” She laughed and said “I love you” as she said many times before, not sure if she meant it or not. I simply smiled back as she told me to sit normally and I did. She pulled down my pants to free my boner and man I was about to cum right then.
I wasn’t the biggest guy in the locker room by all means. I’m not going to lie to make myself feel better on a story that no one I know is going to read or care about. I was about 6 ½ to 7 inches long, and about 2 or 2 ½ inches wide. She began to stroke me slowly while fondling my balls. I let out a deep breath now and then but it wasn’t much.
She began to stroke faster and faster. Surprisingly enough, I didn’t even feel like I was close to cuming. As she was stroking I unstrapped her bathing suit and revealed my first real tits. Like I said, they weren’t huge, but good enough to get any guy hard. Her nipples were erect and I stared in glory. While staring I saw her move over and take my cock into her mouth. She got about 4 inches down and began to suck and lick around those 4 inches repeatedly.
I stroked my hand through her hair and leaned back more. She began sucking deeper, going to 5 or 6 inches. I was breathing heavily and felt I was going to cum soon. She bobbed her head up and downed me giving me a sensation I’ve never had before, but wanted more of. I came and she swallowed. I looked over at Ashley and let out a laugh as she was still asleep.
I turned over to see Melissa getting dressed. “It’s a shame we can’t go all the way” She said. I nodded and frowned in disappointment. The rest of the ride was sat in silence. Although I felt sad for Ashley, I was happy for myself. We arrived home and as I stepped in front of Melissa to leave, she grabbed my dick through my shorts and kissed me. I was hard again and she said to take care of myself. I told her to do the same. She said the final goodbye with “Maybe next time we’ll go all the way”. I just smiled and went home, not even bothering to jerk off.