Chapter 1

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft, Mult, Consensual, Romantic, Heterosexual, True Story, Group Sex, Interracial, Black Male, White Male, White Female, Oral Sex, Anal Sex, Petting, Sex Toys, Cream Pie, Exhibitionism, Voyeurism, Size, Teacher/Student, Public Sex, .

Desc: Erotica Sex Story: Chapter 1 - Jenny and I have our last flings as she prepares to go out in the world after high school. Just one problem - somewhere among all the sex, we fell in love. Can I do what I know is right and let this girl go?

"So thanks again for everything you all did for your schools, and I wish you all the best in your lives. Cheers!"

An echoing of "Cheers!" greeted my toast as all my dinner companions drank from their iced teas and sodas. No alcohol among this group of soon to be high school graduates. Every year I host a farewell dinner for my graduating interns from schools all across town. This year there were five of them joining me for dinner; Jerry, Alex, Carlos, Angie and, of course my favorite, Jenny.

We were eating at a downtown hotel. This was probably the first time a few of them had eaten at a four star restaurant. Appetizers, salads and entries were all behind us and dessert was about to be served. This was also the first time they had all met face to face, although they knew each other from phone calls and IM chats when I would have them help each other out with an issue.

Most of the kids were lively chatting about their plans for their first year in college, the strangest problems they had tackled at their schools and upcoming finals. The only one not holding up their end of the conversation was Jenny. She was quiet at times - glaring at me - other times she would be talking only to drift off in mid sentence.

Right now she was staring at her bowl of sherbert that was just placed in front of her. No one noticed when I tapped my jacket pocket, but Jenny jumped and looked up at me accusingly. I smiled brightly at her and she gave a strained smile back and started to eat her dessert.

When everyone was done and the check was paid we got up to leave. I said good-bye to each one and thanked them all again for their work and finally gave them each a card with an Amazon gift card in it. After some hugs, handshakes and a few tears most of them headed for the garage, Jenny said she was going to wait for her ride in the lobby. I excused myself to go to the lobby bathroom.

I came out a few minutes later to find Jenny in front of the door with her arms crossed and a scowl on her pretty face. "You are a jerk!" she said before spinning on her heel and walking towards the bank of elevators.

Trying to contain my smile, and not doing a good job of it, I stood next to her watching the numbers descend to meet us. "A jerk am I?" I asked as the bell rang out letting us know the car had arrived. She just shot daggers at me with her eyes and stepped into the metal box when the doors opened.

"I can't believe you did this to me!" she nearly screamed once we were isolated in the moving compartment.

"Me? What did I do?" I asked innocently leaning against a wall with my hands in my jacket pockets.

"You want me to tell you." Jenny said getting in my face. Well even with her five inch clogs on, it was more like little Jenny was getting in my chest, but you know what I mean. As the little fireball got going I could see that one day she would be as formidable a person as her mother is. "You get me all worked up, but do you fuck me? No!" she said waggling her finger in my face to make her point."Then you stick this ... this ... thing in me and make me promise not to take it out. Every time I had a coherent thought during dinner its buzzing would make me drool like an idiot. And you know the worst part?"

"Um ... no."

"You could have given me satisfaction any time tonight. You could have given me a cum and then let me be. Instead you just kept me boiling and all I can think about is ... OH!"

As she spoke I touched the remote in my jacket pocket and turned our toy to 'high' for the first time since we arrived at the hotel. Jenny's face froze with her mouth and eyes open wide at this new level of stimulation then her features melted into a mask of blissful agony as she came for the first time tonight. Grabbing my lapels she sank down bonelessly on her knees in front of me just as the door opened on our floor. Quickly turning down the vibrations that set her off I scooped Jenny up before the doors could close and carried her down the empty hall to the room I had booked weeks ago.

Working a key card while holding an eighteen year old girl who was still quivering from a powerful, long delayed orgasm is not as easy as it sounds. Finally I carried her in and put her on the bed. "Oh Mr. S. It's beautiful" She said when she opened her eyes and looked around at all the electric candles I had tipped a bell boy to put out for us. On the desk on opposite wall from us on the bed was a tall vase with a beautiful arrangement of flowers spilling out. I reminded myself to give that bell boy an extra tip, he did a great job. "I love it." Jenny said as she lay on the bed panting and looking around the room.

I took her hand and said,"You know four months ago we were in another hotel room and you gave me the greatest gift I've ever received." She sat up on the white duvet and put her hand on my neck. "You will be graduating next weekend and then going to your internship before college, so this might be one of our last nights together. And I wanted to make sure you know just how special you are to me." Jenny stopped me from saying anything else by leaning in and kissing me.

I lay Jenny back on the bed and stroked her long black hair as I savored her lips and mouth. We had come a long way in the past few months. Tonight I wanted to enjoy everything about this amazing girl. My hand left her silken hair and moved down her arm, over her hip and down her thigh to the hem of the pencil skirt she wore tonight. Jenny and I were still deeply kissing as I traced a wavy line up the smooth creamy skin of he leg beneath her navy skirt. Her flesh was getting hotter and moister the higher I moved. I kissed her cheek and neck before moving on to nibble on her ear. When my hand cupped her wet panties I gave her lobe a harder bite just below the jade stud earrings she had in tonight. Jenny jumped in my arms, thrusting her mound against my hand.

I sat back and looked at this beautiful little nymph who had awakened something in me over this year that I thought my ex-wife had destroyed forever. Jenny smiled at me and said, "I love it when you look at me like that."

"That's good." I said gently squeezing her pussy in slow pulses. I could feel our toy, a small plastic vibrating egg, still buzzing deep within her. "I like looking at you. The only problem is you have all these pesky clothes in the way."

Jenny gave me one of her heartwarming giggles and said, "I think there is something you could do about that."

"Hmm. I think you are right." I said. My hand slipped away from her core back down her leg, this time moving all the way down to her delicate feet. It took me a moment, and both hands, to release the claps on her clogs. I peeled away her left sandal first. Putting it aside I rubbed the tender flesh moving from the heel of her foot up to her toes. She let me know she liked what I was doing with a long moan. I repeated my actions on her other foot and then just looked at her while rubbing them simultaneously.

Jenny's skirt had ridden up and I could see the dark green gusset of her panties between her parted legs. The silky material was obviously stained with her flowing juices from her last orgasm. I inhaled deeply the wonderful scent of her passion. I kissed the big toe on each foot before putting them back on the bed. Moving up to whisper in her ear I said, "I love your smell little girl." She shivered against me.

She was siting up on her elbow watching me with her green eyes that sparkled in the electric candlelight. The fitted white Columbia Bahama shirt had ridden up on Jenny's flat tummy and showed her dimpled belly button. The buttons of the tight shirt strained over her swollen bosom that rose and fell with each quickening breath. Ebony hair cascaded over her shoulders and on her neck sparkled a jade pendant that matched her earrings. A crimson blush still colored her pale face and her lips were parted as she continued to pant for air.

I kissed her quickly before I started to undo the buttons of her shirt. The material parted and I pushed it off her shoulders and pulled it from beneath her. Even though her breasts looked large on her petite frame, Jenny was no more than a B cup and didn't need to always ware a bra. Tonight she went without and her puffy nipples stood tall from being stimulated all night. I kissed each one and then took the right into my mouth and suckled deeply at it. She didn't notice my hand reaching for my pocket until it was too late. Jenny cried out when the egg picked up speed again.

I worked the button and zipper on the side of Jenny's skirt and she lifted her tight bottom so I could pull it down her legs. Sitting back I admired Jenny's beautiful body, covered only by her green high cut bikini panties. At that point I couldn't imagine a more beautiful sight.

Standing up I took off my jacket and shirt. Jenny watched as I retrieved the small remote control from my pocket. I ran the warm plastic across my lips as I considered what to do next. "Please Mr. S. I can't take much more." Jenny pleaded as I watched her. True, she had our little toy buzzing in her box off and on for almost three hours. Before that I had teased her most of the afternoon, building her up right to the edge, but never letting her climax. Apparently her cum in the elevator had just wet her appetite.

I moved back to the bed and traced the curves of her teenage body with the remote control. Jenny reached over and rubbed the outline of my hard cock through my pants. "I want it Mr. S. Please." she pleaded once again.

"Where do you want it?" I asked running the remote over her neck and down to circle her breasts.

"Anywhere. Just give it to me. Now!" Placing the remote control in Jenny's little hand, I grabbed the emerald material on both her hips and tugged her wet panties off her body in one swipe. Jenny spread her legs in a lewd invitation that was hard to resist. Her hips rolled in a hypnotic rhythm drawing my eyes between her swollen lips. Covered in her girl cum, I could see the pink ring of plastic hanging out of her juicy hole by a wire running to the toy that had been torturing her today. Below that was her brown eye shining with the runoff of her wet box. It had been weeks since her birthday when I had last penetrated her dark orifice. Seeing that I knew what I wanted to do first.

I moved away from the bed and took my remaining clothes off, glad to finally be free of them. After rooting around in our bag that had been sent up for us, I turned back to Jenny. Grabbing the covers I stripped them off the bed from beneath Jenny's writhing body. I rolled Jenny onto her belly over a pillow, raising her hips for my appreciation.

Jenny turned her head to one side and shuddered hard as she ground her sensitive, swollen clit against the pillow while her fingers manipulated the remote. Spreading her legs I moved between them kissing, licking and biting the flesh of her thighs until I was nose to nub with her. A long slow lick let me savor her taste from the top of her cleft over her clit and weeping cunt, flicking on the smooth skin of her taint and then circling her asshole before continuing up between her cheeks. I reversed the course back over her willing flesh. This time I stopped and griping the plastic ring with my teeth I slowly pulled the egg out to her opening. I licked around the vibrating pink plastic before shoving it back deep inside her.

Moving down I lashed at her sensitive clit before sucking it between my lips. Jenny was close to another orgasm, and I knew it was time. I raised my head and considered her puckered hole before flicking it again with my wet tongue. After a moment of feasting I raised my head and said, "Jenny, I'm going to fuck your ass."

A wordless moan was her only response, which I took to be consent. I picked up the bottle of lube I had recovered from our bag earlier. She jumped as the cool gel dripped onto her exposed hole. My index finger circled the tight ring of flesh before pushing the lube inside her. I dug one then two fingers into Jenny's inviting ass, stretching the strong sphincter muscle and adding more lube to smooth the way for my upcoming invasion.

When I felt she was ready I sat back between her spread legs and stroked my cock, spreading the lubricating gel over my steely member. I lay my glistening rod along the crack of her ass and kneaded her firm butt cheeks with my hands. Reaching my fingers deep between her enticing cheeks, I spread her taut globes apart, exposing her tight little anus. Jenny groaned deep in her throat as I pressed the bulging head of my cock against her backdoor.

Jenny knew it was coming, but still gasped as I pressed my mushroom tip against the tight ring of her asshole and she yelped quietly into the pillow as the head popped inside and began to surge forward. "You okay?" I asked giving her a second. She nodded her head into the pillow. Slowly and carefully I pushed in until gradually, every inch of my long cock disappeared into her tight passage, and my balls pressed firmly against her young dripping cunt. I stayed buried inside her savoring the vibrations I could feel through the thin membrane from the toy lodged in her cunt.

Very slowly, I pulled back until only the head of my cock was trapped behind the tight ring of her brown eye. After a few seconds, Jenny bucked her hips back in an attempt to re-sheath my cock in her ass. When she was unsuccessful, she jerked her head around to look at me over her shoulder, her teeth clenched and she practically growled, "Don't tease me, Mr. S. Fuck my ass! Shove your monster up my butt. You know I can handle it. Fuck me and fill me with cum!"

This time when she reared her bum back at me, I shoved my hips forward and buried my entire cock deep in her hot hole with a satisfying slap. Each thrust made my balls slap against her drenched cunt. Each time I was buried inside her I could feel the vibrations of our egg tickling my shaft. Little Jenny bit the pillows beneath her, stifling her groans and started churning her hips in a tight, hard circle, fucking for all she was worth.

The slapping noise of our mating filled the room as I fucked in and out of her tight ass, drilling her forbidden hole deep and hard. Every thrust was met by Jenny's rising hips as she fucked back on my slick dick. I was trying desperately to hold back until she came again, but I was losing control. She had already had a cum today, I had not. My hands tore the sheet from the mattress as I tried to maintain control over myself.

Just when I thought I was going to loose it, Jenny slammed her hips back a final time, fucking herself on my hard flesh and holding me captive. I could feel the egg jump into high gear again as she pushed herself over the edge. Jenny screamed so loud I had to cover her mouth with my hand before hotel security came to see who was being murdered. Her orgasm rolled over her like crashing waves as she buried her face in the pillow and screamed again and again. That was all I could take. My primal urges took over and I started to piston my hips until I blasted off, blowing my load of gooey cum into my young lover’s tight asshole. My world shrunk to just the burning white hot ember of my climax until I finally collapsed on Jenny's sweat-slicked back, my cock still wedged up her bum.

Slowly, my cock shrank and slipped out of her rubbery asshole followed by a stream of my pearly cum. I wrapped Jenny in my arms and rolled off her, pulling us both onto our sides, and hugged her tightly. Between gasps I leaned in and whispered, "You can take it out now." Jenny quickly reached between her legs and pulled at the ring until the pink egg slipped out of her drooling cunt.

"Oh God Mr. S." She panted holding the toy up watching her juices shine on its hard plastic. "That was something else."

"I hope that was worth the wait." I said as I nuzzled her silky hair and kissed her hidden neck.

After we had cuddled for a few minutes I got up and went to the bathroom to wash up. When I came back I admired the way Jenny's smooth, creamy skin glistened with a thin film of perspiration, the same perspiration that matted her long black hair to her forehead and neck. Her firm teen breasts still heaved with each deep breath and her red, swollen nipples pointed to the ceiling. The bald lips between her thighs glistened with sticky girl cum, but it was my cum that pooled in the crack of her ass.

As I stood over her staring at what was undoubtedly one of the most erotic images I had ever seen, Jenny's eyes fluttered open and she fixed her weary gaze on my large cock and smiled weakly. Her full sexy lips cracked into a grin. "Hey there, Mr. S." she croaked, "You look ready for round two?"

"Maybe. How about you."

Jenny spread her legs wider and said, "Come and get it." My cock was throbbing at her invitation and rose to point the way to the bed as if it recognized her open pussy waiting to be filled.

"Still think I'm a jerk?" I asked as I crawled between her beautiful legs. Her only response was to moan, and shake her head gently as I nudged the slick lips of her pussy with my tongue. Jenny is a juicy little girl, but she wasn't the only one I could taste. My cum had run over her lips and for a moment I thought about how that cum had spilled from her ass, but her cries of pleasure spurred me on. I locked onto her clit and suckled at that hard flesh. Her hips resumed their thrusts and hard circles until I could barely stay in the saddle.

Knowing we were both ready I sat up and ran the head of my rampant cock across her opening. Jenny may have been tired, but as soon as I started to slide my thick pole into her wet box, I felt her pussy muscles tighten on me like a vise, and her hips rose off the mattress, impaling herself fully on my cock.

Sensing how tired she really was, I gently reached back and took hold of her legs, and eased them over my shoulders. In this position, I could really drive deep, and she could lay back and enjoy the sensations as I did all the work. Picking up the pace I fell into a hard, pounding rhythm that I wouldn't have dreamed of using with her months ago. My hips slapped wetly against her sticky ass as I drove into her tight hole again and again. Jenny's eyes were shut tight and her face was contorted in a ridged mask of lust.

Jenny began to cry and moan with each thrust as I fucked her mercilessly. "Oh God! Oh God ... fuck me! Fuck your slut! Oh fuck my slutty cunt!" She cried while my savage pounding made her sweet teen tits bounce up and down on her chest. Unable to resist, I bent my head and took one stiff nipple into my mouth and sucked hard. Jenny moaned at this new sensation, and when I closed my teeth over the hypersensitive nub and bit down, she slammed her pelvis against my groin and her mouth dropped open in a shrill scream of ecstasy.

The strength and duration of her orgasm took me by surprise, and it seemed like minutes later she continued to thrash her hips up and down against me, her eyes opened wide and locked on mine. Her energetic reaction to our aggressive fuck set me off and I slammed all nine inches of thick cock meat deep inside my teenage lover and screamed as I released my jizz in her cunt. Jenny's beautiful green eyes widened and she cried out again until we fell together on the bed shaking and quivering all over.

We lay panting and gasping in a sweaty heap. Finally I pushed myself off Jenny's little body and rolled next to her limp form. Jenny snuggled against me and I hugged her close. Once we could breath again she looked up at me with her bright eyes and said, "Thank you Mr. S. I forgive you for torturing me all day."

"Good, because tonight I think you nearly killed me." I said kissing the tip of her nose and then cuddling her back to my chest.

"Mmmm. Nice to know for an old man you can still work so hard."

"Why you ungrateful..." I complained smacking her bare bum. Jenny squealed and then broke out in her childlike giggles.

Jenny looked at the clock and then said, "Mr. S, I have to get going soon. Mom want's me home by midnight." The clock said 11:07.

"I wish we could stay. After all we do have this great room all night." I said as I watched Jenny sit up slowly and move to the edge of the bed. Her bum flexed as she stood up and she squealed, cupping her hand over her cunt and ass where our juices were starting to pour from her. Jenny scrambled to the bathroom and I heard her sit on the toilet. I gave her a few minutes to finish up before getting up to go in and ask, "Want a shower?"

"A quick one. Want to join?" She asked saucily waggling her butt while looking back over her shoulder as she stepped into the tub. Without answering I stepped in after her and caressed her wet body. "Hey mister! I said a quick shower. You get me going and I'm going to be late. But if you are good you can wash me." she said handing me the soap.

"Damn you winch." I said lathering her back up before moving down to her tight ass and toned legs. She turned and I worked my way up, taking time to gently clean her lovely pussy and sensitive asshole, before moving up her tummy and soaping her breasts.

Jenny then took her turn to lather me up, getting every nook and cranny. She was kneeling in front of me when she asked, "Are you coming to my graduation next weekend, Mr. S?"

"I will if you want me to."

"I want you to." she said standing up rubbing her breasts against me all the way up.

"Then I'll be there. But if you plan on getting home on time, you better stop doing that." I said indicating her hand pumping my stiffening cock.

"Aww. But he likes it. And I won't get to play with him all week." she said in her little girl voice.

"Do well on your finals and you can play with your toy." I admonished her as I turned off the water. Drying Jenny's nubile frame didn't help ease any stiffness in my groin, but I wasn't about to start something we didn't have time to finish.

"If I do well could you take me where you got my egg and get me something else?" She asked as I knelt in front of her rubbing the towel on her rosy skin.

I looked up at her and asked, "You want to go to the adult book store?" My cock gave a reflexive leap at the thought of this cute teen pursuing the shelves of a triple X store.

"If I do well in my tests it will be my reward. She said stroking my hardening cock. "But I can't leave you like this. Hold on one sec."

Jenny left me to finish drying in the bathroom and I heard her on her cell phone. Moving to the door I could hear her end of the conversation. "Yeah ... No it's all good….Uh-uh, he's still worked up….Okay, one o'clock at the latest ... Yes ... MOM! OMG! I am NOT telling you that ... Yes I'll be careful. See you soon."

Coming around the corner I asked, "What was that?"

"Just getting an extension on my curfew tonight." she said coming back to hold her naked body against mine.

"And why would you do that?" I said running my hands over her naked flesh.

"So I could do this." she said and sank down in front of me. I looked into her eyes as she opened wide to take the head of my semi-hard cock into her mouth. Her little tongue swirled over my sensitive glands. Bringing both hands up to grip the shaft, she started to suck on the first few inches of my stiff flesh. One hand left my cock and moved down to caress my hanging fruit, spinning the balls between her fingers. Jenny moved her head taking me deeper and deeper with each thrust.

Sitting back Jenny released me from her mouth and pumped my shaft with her tiny fist. The first gob of spit that flew from her lips was a shock. She had never done that before. She rubbed the fluid over me, using it as lube. She spat again and again until it was dripping off my vainy shaft. Her other hand had released my balls and was busy between her legs until it came up and she started to circle a slick finger over my asshole.

I groaned and Jenny leaned in to lick my balls. Reflexively I spread my legs further to allow this little slut the access she needed. Then another first, she went further back and licked my puckered hole. I had never felt this sensation, but after only a second I realized I liked it. Raising my foot to rest on the desk chair I gave Jenny a sign to continue her analingus. She pierced my bum with her sharp tongue and the feeling of that flesh wriggling in my ass was enough to make wads of cum spurt from my straining cock. I grunted as she fisted my cock encouraging the drizzle of jizz. Only after I was fully tapped out did she come out from between my legs. She licked the cum off my cock then getting everything that had splattered on my belly and legs. Only then did she sit back and start licking her hand like a cat. When: she had lapped up all of my spend she smiled up at me and asked, "All better."

"God yes!" I said sitting in the chair. I pulled her up into my lap and kissed her, tasting my cum and ass on her lips. We sat like that for a few minutes enjoying the feel of the others naked body. "You are too quiet, what are you thinking?" I asked.

"I don't want to do that internship this summer." she said quietly.

"Why it is a great opportunity if you want to study computer science."

"I'll just be getting people coffee." she complained and I could picture the pout that was on her lips.

"You'll be getting coffee for some of the greatest minds in Silicon Valley. You know how many people you beat out for this chance?"

"But ... I don't want to leave yet." she said softly into my neck.

I squeezed her tight and said, "We knew this was coming sweetie. You have your life to live. I'll just drag you down."

"Mr. S. you don't drag me down. I'm doing better than ever. You have been so great for me. And ... I ... I love you." she confessed looking through tears into my wide eyes.

"Oh God Jenny. I love you too."

"Then I should stay!"

"No sweetie. You should go. I will always love you. I will always be here if you need me. But I need you to go. Do this internship. Go to college. Meet some guys your age and have fun. You need to be a girl, and have a life of your own." Tears were falling down my face too. Jenny's departure was the last thing I wanted. But I also knew it was best for her.

We sat with Jenny cradled in my arms until all our tears were shed. I took a tissue and dried her eyes and cheeks. She blew her nose while I cleaned myself up. Finally we could look at each other again and she told me, "I'll go, but I'm not going to stop loving you or wanting you."

"And I'm not going to stop either." I said before kissing her tenderly.

"Promise I'll see you on Friday?"

"Promise."

"Okay, and I'll tell mom I need to have a full day with you before I leave." Jenny said standing up.

"Good." I said then dug our clothes out of our bag. Watching her get dressed was always a bitter sweet experience. I gathered all the candles and gave her the egg after it got a thorough cleaning. Finally with her holding the flowers we were ready to go.

Our conversation was light as I drove her home in my Mustang, and stayed light until we reached her driveway. I could see the lights on and knew Kat was waiting up for her daughter. Jenny looked at me and said, "I'll do it. Pass my finals, the internship, college. I'll do it because I want to, but also because ... because you want me to."

"You'll do great, just do it more for you than for me, okay?"

"Okay." she said. "I'll talk with you soon." With a final kiss she got out and I watched her juggle her flowers and clothes as she let herself in the house. Only then did I slip the car in reverse and head off. All I could think was, Fuck, when did we fall in love?

When this story gets more text, you will need to Log In to read it