My First Time 294

We all remember our firsts, right? I was the odd/shy guy in school. I wasn't the coolest guy in High School not even close if I'm being honest. I was friends with Jack who was the coolest guy in school. Because we lived on the same street growing up. We remained friends in High School. We were both on the wrestling team so we were bonded by that and he didn't let the other guys fuck with me. Being a wrestler and his friend afforded me invites to parties I really shouldn't have been invited to in the first place. My social standing in school was often a disadvantage. I wasn't a bad-looking guy but I lacked the muscles the jocks had. When we started Senior year I had just turned 18. I had put on some muscle from working out with my teammates over the summer. Because of this turn of events, I gained access to a whole new caliber of girls in school.

I knew who was dating who and I knew who the available girls were I had my eye on a couple of them. I would talk to the single girls and stay away from the ones my teammates were dating for the most part. Except for Tina Morris, she was dating my neighbor and we became close. He knew that I wouldn't do anything with her because of our friendship.

Tina was right out of the Sports Illustrated swimsuit issue. She was a brunette with big tits had amazing nipples and kept her pussy neat and trimmed but the landing stripe was nice and thick. She sent me a pic by accident and I replied back that she had sent me the file by mistake. She said if I wanted to look at the picture it was cool with her as long as I didn't tell Jack or share it with anyone. I agreed with that. She came to school the next day and cornered me in the hallway next to my locker.

"Did you look at the picture?" She asked. I looked at her and smiled.

"I did and damn girl Jack is a lucky fucker," She smiled and leaned into my ear.

"Could you return the favor after school?" She whispered. My face turned red as I looked at her.

"You're serious? Okay but the same deal you don't tell Jack and you can't show anyone," She nodded her head and agreed. We walked into class and she sat beside Jack like she always did. After class, we walked to the lunchroom. I sat with my friends and Tina joined us. She wanted to hang with me for lunch. I didn't mind. I enjoyed her company. Jack came over and joined us sitting between me and Tina.

That's odd.

After we finished eating lunch Jack asked me to come to his locker with him to get a book. He wanted to bring it back to the library. We got to his locker and he opened it.

"Bro, what's going on with you and Tina? He asked? I looked at him unsure what to say.

"What do you mean man? We're friends," I said. He took a book out of his locker and put it in his backpack. He slung his backpack over his shoulder. As we walked away from the locker he grabbed me slamming me against the lockers.

"Stay away from her. She's off-limits. I've never had to ask you this before but I'm asking now," I looked at him in disbelief for a moment.

"Of course Bro, She's your girlfriend we're friends. Tina came around the corner seeing Jack with his hands full of my jacket. She jogged up to us.

"Let him go Jack damn it! He's your friend. Why would you do that to one of your oldest friends? I adjusted my jacket and turned to go to 3rd-period class. Tina smiled at me.

"I'm sorry Jay," she said with a hint of sweetness in her voice. I nodded to her and went to class. I was thinking about what Jack had done and said to me. I was working on some math homework in study hall when Tina walked up to my table and sat down. She did her social studies work. I finished my work and sat there watching her write. Her hair was different she was hiding her face.

"You okay Tina?" I asked her. She turned her head to reveal she was crying. "What is it?" I put my hand on her shoulder to comfort her.

"Jack went off on me for interrupting him earlier with you. What was he saying?"

"I don't want to get into it. It was nothing he's worried that we are getting to close to each other,"

"He has this weird thing where he believes that guys and girls can't be friends. If they are friends they must want to fuck each other," We both laughed. I gave her a side hug. "You have a bunch of girls that you hang out with and how many of them have you fucked?" She asked? I looked at her for a moment. I didn't want to answer that question. I shrugged my shoulders. "Oh no you have to tell me now," she said looking at me anxious for my answer.

"None I haven't fucked any of my female friends," I said as I put my head into my hands. She got close to me. She leaned into my ear.

"You're a virgin?" She asked? I looked at her and nodded my head.

"You go to the parties and spend a lot of time in rooms with girls. Surely you've gotten a blowjob or a nice handy before, right?" I shook my head. I leaned into her ear.

"I prefer to give oral sex or flange sex than receive it," I said to her she smiled

"What a gentleman," She said as she gave me a quick hug I hugged her back.

For the first time since I'd known her, I started to get hard for her. I pulled away from her unsure what do to at that point. I got up and went to the soda machine and got a soda I got her one as well. I got a bag of chips to share as well. I sat down at the table and handed her the soda and put the chips between us. She opened them and took one.

"It was my turn to get the snacks," she said pushing against my arm. I took a chip and dropped it on my lap she looked down and I was busted. She smiled as I picked up the chip and ate it. She looked me in the eye and smiled.

"Show it to me, I dare you," She whispered. I shook my head no. I looked around she stood up and leaned over giving me a peek down her top her tits were perfect. "Come on a flash," She whispered. I looked around and we were in the corner so no one could see me. I unzipped my pants and pulled my hard seven-inch veiny cock out and showed it to her. I put it away and she smiled.

"You're huge!" she said with a smile. I can see why Jack keeps you as a friend you would get so much pussy with that monster," she said. I laughed at her.

"I don't get a lot of pussy. I've never even seen a girl naked outside of a yahoo chat room," I said.

"Ever gotten head or a handy?" She asked? I looked at her shaking my head.

"Wow! That's amazing. I know a few of the girls that would love to do that for you. You have a lot of girls who would love to date you," She said as she took another chip from the bag. After study hall my cock went back into hiding. During 4th period Jack and I spoke about Tina and what happened after I walked away from them in the hallway.

"Did she cry to you in study hall?" He asked? I nodded my head. "Figures. Look man I'm stressed with school and college stuff. Can we forget about earlier?" He stuck out his hand and we shook hands and did the bro hug. It was a dead issue. I walked out to the bus alley to get a ride home with Jack and Tina. I saw Tina standing alone. I walked over to her and didn't say anything at first. She turned and saw me.

"Jack told me to take the bus home he was heading to the gym to blow off some steam. Will you sit with me on the bus?" I nodded my head and we got on the bus. We sat on the bus waiting to ride home. She leaned her head on my shoulder.

"Are you still going to send me a picture of it?" She asked? I shrugged my shoulders.

"Come on!" She begged. I smiled at her and nodded my head. We got off the bus and she went to the other side of the road. She lived on the other end of the street from me and Jack was between n us. I went to my room and took out my webcam and set it up to take the picture for Tina. I got it well lit and set in the chair I put her pic on my screen to use as motivation. I took a couple of good ones and sent them to her. I got dressed and then got a snack. I was getting ready to go on a run before dinner I put on my shorts and tank top. I had my headphones in as I jogged to the end of my driveway. I turned on my music and set out down the road. I passed Jack's house and he waved to me he was with Denise a cheerleader, with big tits and blonde hair. They were holding hands. I passed Tina who was jogging in the opposite direction. I turned around but I was too late Tina saw Jack with Denise holding hands on his porch. She jogged up the driveway and busted them. I jogged up the driveway to help in any way I could. Tina broke up with Jack and walked away.

"You're a dumbass. Throwing away a five-year relationship for a night of fun with the town bicycle," I said before I jogged away. I caught up to Tina who was crying we went on a jog to blow off steam we decided to jog down the trail behind the houses. We stopped for a water break. She took a drink from her bottle of water. Seeing her sweaty body glowing in the sun was different than I'd ever seen before. She smiled at me. I smiled back.

"I got the file by the way. Nice. I liked seeing it in person more," She walked over to me and we sat on a log. She sat close to me. She took her little black bag off her shoulders.

"Why did you bring that thing with you?" I asked? She put it between her legs. She took another drink from her bottle of water.

"I couldn't get our earlier conversation out of my head. and I was thinking if you want I could give you your first handy," I looked at her for a moment unsure what to say or do. She leaned in and kissed me on the lips. I kissed her back she put her hand on my cock as it started getting hard in my shorts. I slid my hands up her body and touched her tits through her sports bra. I touched her nipples and they were erect and she grabbed my hard cock in my shorts.

We continued to kiss. I moved to her neck and kissed it licking slowly to her ear.

"I want to eat your pussy," I whispered as she nodded her head. We stood up and she took her shorts off she wasn't wearing panties. Her beautiful thick landing strip pubic hair and pussy were sweaty and smelled so good. I laid my sweatshirt on the log and she sat on it I knelt down and she spread her legs and kissed her thighs. And licked her clit softly a few times teasing it.

"Wow. That feels so good!" She said as I continued to lick her clit like it was my job. I slipped a finger into her tight pussy as I worked my tongue around her clit in small slow circles.

"Oh fuck yeah. Like that," she moaned as she laid back on the log and played with her nipples. I fingered her pussy and licked her clit. I felt her legs begin to shake as I slipped a second finger into her honey pot. She put her hands in my hair and held my face tight against her pussy as she came all over my fingers and face. I continued to eat her pussy I wanted to make her cum more. I slipped my fingers deep into her pussy. I licked her clit faster and with more pressure than before she pulled my hair as she came again and again. She released my hair. I cracked my neck and I helped her sit up on the log.

"Wow! That was fucking incredible, You really are good at that," she said. I stood up and took a drink of water from my bottle. She put her shorts back on. She untied my shorts and pulled them down to my thighs. My cock was already hard. She opened her bag and pulled out a bottle of Astroglide. She sat me on the log and poured lube on her hand and rubbed it along my cock slowly at first.

"I want you to enjoy this you can cum whenever you want to but if you can hold off that would be cool. If you can hold off the orgasm will be better too," She said as she slipped her hand along my cock. My balls were so tight as her hand slipped along my prick.

"I've always wondered what this would feel like with someone else doing it," I said she looked up at me and smiled.

"From me or anyone?" She asked? She gripped my cock hard waiting for the answer.

"From you," I said as she took her pointer finger on her free hand and wiped a bit of pre cum off my cock head. She licked it from her finger. "That's hot," I said as my orgasm built.

"Where do you want to cum?" She asked as she started to quicken her pace.

"I can let it fly if that's okay with you?" I said as my legs started to tighten up.

"You could cum in my mouth, its flavored lube. Let me know when your gonna blow and we'll figure it out," she said. She continued stroking my cock as I began to sweat under the warm sun. seeing the sweat running down her back as she beat my cock.. My legs stiffened I looked down at her she was smiling as she gave my cock a squeeze.

"I'm gonna cum!" I moaned as she jacked hard and fast.

"Let it go!" she said. I lost control and my load shot out of my cock all over her face and tits she kept jerking my cock after I came. She licked a bit of cum off my cock and then pulled a small towel from her bag. She wiped off her tits. She then licked my cum off her face which was so hot to me. We got dressed and I walked her home. We sat on her front deck when we got to her place. She leaned her head on my shoulder as we watched the sun going down. She took me by the hand and gave it a squeeze.

"I want you to know that what we just did for each other doesn't have to change our friendship. I wanted to do that for you even if we hadn't caught Jack cheating. You're special to me and I wanted there to be something special between us," she said with her head on my shoulder.

I kissed her on the top of her head and she took her head off my shoulder looking into my eyes. I kissed her softly on the lips she pushed me back against the bench and straddled me. As we continued to make out. I put my hands on her ass as wrapped her arms around my neck. We kissed she pulled off her sports bra and put my hands on her tits. I held them and squeezed them a bit before she pushed my face down into them I licked them, nibbling each of her nipples. My cock got hard in my shorts pushing against her pussy she moaned. She pushed her hips down into mine rubbing my cock with her pussy through our shorts. She pulled my hands off her ass and pushed them down her shorts. I grabbed both of her sweet cheeks in my hands.

"Should we go inside?" I asked? Her ass fit perfectly in my hands. As we kissed again now moving to french kissing. Feeling her tongue wrapped around each other and my rod was stone hard.

"We can fuck right here. I have a condom in my bag," She said as she got up and took off her shorts. I pulled my shorts down and she reached into her bag and pulled out a condom. she handed it to me I opened it and rolled it onto my hard prick.

She straddled my legs and lowered herself onto my cock slow and steady.

"Fuck it's so big!" She moaned as took it balls deep. She bounced on it hard and fast as we kissed passionately. I held on to her ass cheeks digging into them as she rode me hard. Listening to her pant while she rode my cock was so intoxicating.

"Want to try it from behind?" She asked? I nodded my head and she got up and bent her perfect heart-shaped ass over the bench. She guided my engorged dong into her wet pussy and I pushed it in balls deep. I pumped slow and steady.

"You can go harder. Do what you want I can take it," She said as she looked over her shoulder. I put my hands on her hips and pushed in hard and fast my balls slapping against her clit. She moaned as I went to town on her pussy.

"Fuck I'm gonna cum all over your cock Jay! Don't stop fucking me," She moaned as her legs started to shake. I could feel her juices dripping onto my balls. I knew I wasn't going to last much longer. She started to rub her clit as I pounded away.

"Cum inside me James I want it, baby," She said and I pushed into her balls deep hard as I filled the condom with cum. I pulled out and took the condom off and put it in the trash can on the deck. I put my piece away and she put her shorts back on. We turned around to see Jack standing on the porch he had watched us fuck. He looked at me and then at his now ex-girlfriend. He walked away as we sat back on the cum soaked bench together.

"How was it?" She asked? I didn't say anything for a moment.

"It was better than all the times I jerked off thinking about fucking you," I said as I kissed her head again.

"Why didn't you say anything before?" I wanted to date you for so long. I thought you had no interest because I was with Jack," She said as she got up and walked to the door of the house. She walked inside. I followed her.

"I didn't say anything because you were or I thought you were out of my league. I didn't think you would like someone like me," She went to the cupboard and got some crackers out. She then to the fridge and got some pepperoni and cheeses to make a snack plate for us.

"Well, I think we both know now how well we fit together. In more ways than one," She said as she put the snack tray together with a smile on her face. Her mother came in from outside.

"Hello James, it's nice to see you. It's been ages. How are you? She Asked?" I looked at her and then at Tina.

"I've been well. I think you're gonna be seeing more of me Mrs. Morris," I said as Tina picked up the snack tray.

"Mom we're gonna go play video games can James stay for dinner?" She asked?

"Of course, he can. A nice guy like him is always welcomed here. I prefer him much more than that caveman Jack," she said with a laugh.

"Jack and I are finished we caught him redhanded with that skank Denise. James is my guy now," she said. We went downstairs to the basement. As we played games she looked at me.

"As I said earlier what happened today doesn't have to change our friendship unless you want it to change?" She said as she took a piece of cheese from the plate and fed it to me. I smiled before I bit the cheese.

"I think we should give this, give us a try," I said as I took a piece of pepperoni off the plate.

"What about Jack?" She asked.

"He'll have to get used to it. I mean he's the one who really ended things with his actions. He is the reason you broke up with him. He has no one to blame but himself. If he wants to hate me that's on him. I'm only worried about making you happy and keeping you that way,"

We finished the snack plate and had dinner with her mother and as I left her house that night we kissed on the porch. What a day that was. I'll never forget Tina Morris...