tagFirst TimeMy Friend Jessie

My Friend Jessie

bySkipper_Malone©

I had just stepped out of the shower when I heard the front door open. I haphazardly wiped myself off and slipped into a t-shirt and sweatpants and walked downstairs into the kitchen.

"I'm back Adam," Jessie said, placing two brown bags of groceries onto the kitchen. "You didn't have any food here so i went out to the farmer's market and got some stuff." She said as she tied her long dark brown hair into a ponytail.

"Aww c'mon now Jess, you didn't need to do that." I said as I hugged her. Her 5'6 slender body was small against my 6'2 muscular frame. I for one have never been a big hugger, but she seemed to like it when anyone hugged her.

"It's the least I could do Adam. I'm staying in your house for one week, I should at least get some food for us." Jessie's parents were out on their second honeymoon for their 25th anniversary, and my parents were on a couples retreat in Bora Bora. Since neither of our parents were home, I decided to let Jessie stay at my house for the week.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

I had first met Jessie Slayton in our freshman year of high school. Jessie had moved to my suburban town in New York that year. Like me was a very intelligent. When I walked into my Chemistry Honors class that day, I was assigned a seat at a workstation near the back. The stations were set up so that a pair of people could sit together and be lab partners. I walked to my seat and found a pretty girl sitting at the station next to mine. I sat down at the seat marked "SIMMONS, ADAM" and took out my books. Just as I sat down the bell rang and the teacher started class.

"Class, it appears that we have a new student with us today. Everyone say hello to Ms. Jessie Slayton. Jessie, introduce yourself to the class" the teacher, Mrs. Crowley said. Jessie, who I discovered was the girl sitting next to me at the workstation, stood up.

"Hi everyone, I'm Jessie and I just moved here from New Jersey. I hope to have a good year with everyone here!" She said as she sat down. Mrs. Crowley started to drone on about the usual things teachers talk about on first days, and I took this chance to talk to Jessie.

"Hey there Jessie, I'm Adam. Looks like you're stuck with me as your lab partner this year."

"Ha yeah, I guess so. That can't be too bad Adam." Jessie said with a smile of her own. I was struck by how white her teeth with and how beautiful her face looked, framed by that brown hair of hers.

We became friends very quickly. She didn't know anyone around town, so I helped familiarize herself with the school and the rest of town. She has been my only constant friend throughout high school. I was a somewhat late bloomer in the puberty department. I had always been a really small, scrawny nerd throughout elementary and middle school, interested in computers and online gaming. I had always wanted to play football, but due to my size I never played. During freshman year I grew from 5'5 to 6'1 and began to gain muscle. I pushed myself to exercise hard and became stronger. I eventually deemed myself ready to try out for the football team at my school.

I surprised everyone by making the varsity team at tight end. I befriended most of the senior players, and was frequently invited to parties. I started to abandon my introverted nature, and alienated most of my old friends. I moved up the social "chain", and became one of the most popular guys at school. With this, I started to get alot of attention from girls at parties. I lost my virginity on my 16th birthday, which was in January of my sophomore year, and quickly became known as a stud. But all of that empty sex just couldn't compensate for what I really wanted: somebody to love. My 18th birthday had passed and it was senior year, and I had yet to have a serious relationship before.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

"So what are we doing tonight?" Jessie asked as she walked into the living room. She had changed into a pair of short denim shorts and a black tank top that gave a limited view of her midriff. She had let her wavy brown hair down. I liked it when she did this. "Are we going out? Staying in? Throwing a wild party?" she said with a smile.

"Actually, I was thinking of just staying in an watching a movie or something." I answered. I opened up Netflix on my Playstation 3TM while Jessie went to get two beers from the refrigerator I kept hidden from sight in the basement of my house. She returned with two bottles and placed them on the coffee table. I found one of my favorites, When Harry Met Sally, and put it on.

For some reason, it felt different. Something was not like it usually was. I had watched movies with Jessie all the time, but this just felt different. Maybe it was the subject of the movie, or maybe it was the way I could see Jessie's cleavage when she leaned over to get her beer from the coffee table. Before I knew it the movie was over. I was lost in my own thoughts until Jessie snapped me out of it.

"Oh c'mon, that was silly. Guys and girls can be friends without them being attracted to each other? Right?" Jessie said. I had a realization in that moment. I had not had a relationship all this time because the girl I should have been with all these years was right in front of me. I looked into her deep brown eyes. They were looking at my own eyes, and they had that shine only she could have. My lips came closer to hers. Her lips that contained her smile, that formed her words, that allowed her beautiful laugh to escape. Our lips touched and shock waves went down my spine. I had had many kisses before, but none that felt this right before. My tongue pressed against her soft, warm lips, begging for entrance. She let me in and our tongues began to move in sync with each other. Jessie's hand rest on my thigh and she began to stroke my thigh. As she did this, my cock began to spring to life in my sweatpants. I nibbled my way down to her neck and rest my head on her shoulder.

"I don't know how else to say it Jessie but.." I paused to continue nibbling at her "I love you. You're all I've wanted all these years and I've never been able to express it until now."

I looked Jessie in the eyes as I said this. She smiled and whispered to me in the sexiest voice I've heard "I want you to be my first," as her hand moved to my crotch. I didn't need to be asked twice. My hands traveled to her full, rounded breasts, and I rubbed her aroused nipples through her bra. A soft moan escapes Jessie's mouth as I continue to knead her breasts through her bra and tank top. Jessie helped me take off her tank top until only her lacy black bra remained. My right hand continued to tease her erect nipples through her bra while my left hand went down to working the zipper of her denim shorts. After I undid the zipper Jessie maneuvered the shorts down her legs until they fell to the floor. Jessie then helped me out of my t-shirt and that fell to the floor next to her shorts. I plunged my hand into her black satin panties and felt the heat escaping from her pussy. I continued down her trimmed bush and whispered in her ear "What do you say we finish this upstairs?"

Jessie wrapped her legs around my waist and I placed my hands around her round, firm ass for support. I lay her down on the bed and stand at the foot of the bed. I continue to kiss her as I undo the strap of her bra. I remembered that her bra size was 34C from the time we went shopping and she dragged me into Victoria's Secret to buy underwear. I recognized the panties she was wearing were the same pair she bought that day. They felt similar now as I pulled them down inch by inch down her legs as the time that she told me to feel how smooth they were. I had pulled her panties down to her feet and finally pulled them off. Jessie, my best friend, was now naked on my king sized bed in my bedroom. I climbed on the bed and kneaded her full, round breasts with my hands. I teased her pink nipples, which were now hard as rocks, by placing them between my forefinger and thumb and giving each a slight rub. Soft moans escaped her mouth as I continued to tease her. I moved my left hand down to her exposed pussy and ran my finger around her opening.

"Oh Adam...please...I can't wait any more..." Jessie moaned as I ran my fingers around her lips. I put one of my fingers into her pussy and a loud gasp escaped Jessie's mouth. One finger turned into two, and I continued to massage her pussy. I took her clit in my mouth and I began to slowly suck. Jessie continued to moan and pant as I speeded up my pace with my fingers. I brought my face up to look her in the eyes.

"I want you to cum for me Jessie. Be a good girl and cum for me." I said in a commanding voice. I felt her hips buck and loud screams came from her mouth. Wave after wave of her orgasm hit her as her toes curled and her fingers scraped into my back. After Jessie's breathing had returned to normal I felt her hands start to explore inside my sweatpants. I lay down on the bed next to her and she started to climb onto me. Her hands worked the waistband of my sweatpants and pulled them down my legs until they slipped to the floor. My 7" cock sprang free. Jessie's small hand was around the shaft of my cock as she lowered her head down to the head. Her tongue wrapped around the head and slowly licked up and down from the head to the base. She took my cock into her mouth and her warm lips wrapped around my cock. Jessie continued to raise her head up and down on my shaft, continuing to suck on my cock. After a little while I told her to stop and get on her back. I spread her legs and got a full view of her pussy.

"Are you sure you want me to do this Jessie?" I asked one last time for assurance. She nodded slightly to assure me that she was ready, and I plunged my cock into her slit. I started slowly at first, allowing her to adjust to my shaft. She cried out in pain at this new sensation in her; she was not used to this. I felt sorrow as I heard her scream. I asked if she was ok, but she nodded her head yes and bit down on her lip. I slowly took my member out of her pussy and then slammed it in again. This time, not a scream but a moan escaped Jessie's lips. I soon started to increase my pace. Jessie moaned and moaned as I continued to pound into her sex. Jessie opened her eyes and I saw her eyes glow. She pleaded for more as I continued to go into her. Jessie screamed as I pumped into her and I felt her hips buck for a second time. Her back arched and I felt her climax tear through her. Her muscles clenched against my cock and I felt myself release. My nectars coated her pussy as I came in her. I fell next to her. Jessie gave me a quick kiss before getting up to do whatever it is girls do after sex in the bathroom. Jessie returned and curled up next to me. We continued to kiss and nibble at each other as both of us fell asleep.

Rays of sunlight peeked through the blinds of my bedroom window. I awoke and curled up to my side is my best friend Jessie, sound asleep, her head resting on my left pec. I move slightly and she sleepily moves herself off of me. I go downstairs to the kitchen to make us both a cup of coffee. I returned to my bedroom with two mugs. Jessie was now awake, sitting up in my bed naked. I climbed in next to her and handed her a cup of coffee.

"So...was that I dream or did last night happen..." I said as my voice trailed off.

"I hope it wasn't Adam. Last night I realized that you were the one for me. After all these years I have finally figured out that you and I should be together." Jessie said. I smiled and kissed her on the forehead.

"I realized that a little bit ago, but I haven't been able to express it just yet. I guess we're boyfriend and girlfriend now?" I said with a smile.

"Like we haven't been already all these years Adam." Jessie said, playfully slapping me on the arm. I kissed her again, a passionate kiss.

"I love you so much Adam." Jessie said as I released.

"I know," I said, "and I love you too.

Report Story

bySkipper_Malone© 10 comments/ 27552 views/ 6 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartburninglove, tjdhall2 and 4 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous10/04/13

really good

you should comment how u guys are doing now

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous09/27/13

Nice short story

Many friends are in the same situation. Neither wants to make the first move. It is better to take a chance than regret it. It is wonderful when both realize the true love.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Skipper_Malone09/26/13

Accusation of copying

Thank you for drawing this to my attention Anon. I commented above that this is based off of real events. Of course, this is the internet, and nobody's word is valid on the internet, so I greatly apologizemore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous09/25/13
by Skipper_Malone09/25/13

"Total Fucking Rubbish"

Thanks Anon for your comment, means alot to me!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 10 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel