Bobby Jo
Introduction:
Young man’s introduction to sex
We first met just after I started junior high school. I had entered the seventh grade like many others, in that I was awkward, felt alone and out of place most of the time. Miss Bobby as she was called singled me out on my first trip to the library in search of a research book. Even at that moment in my backward way I felt she had strange and wonderful things planned for me. What they would be was beyond my comprehension but I still felt they would be wondrous.
When I noticed her watching me I defiantly returned her stare for a few moments, then hesitantly walked toward her. As I approached my eyes darted down to peek at her inviting puckered lips then on down to her large breasts. Her lips looked to be in a naturally puckered ready for a kiss pose. I asked where I might find the book I needed and she smiled almost wickedly as she placed her hand on my shoulder and said “ how portentous you should ask for that book, this way” guiding me down the aisle into a dimly lit corner that was out of sight of everyone else where she pointed out the book.
When I turned to thank her she moved forward and placed those always pursed lips against mine in my first real kiss of passion. I stood there shocked and when I didn’t pull away she slipped her small wet pointed tongue into my mouth and probed me frantically. I had no prior experience with kissing and was at a loss what to do so I pressed back then began to push my tongue into her mouth. I loved the feel and taste of her as she continued the long wet kiss. Her smell was so fresh and sweet it made me want to lick her skin. The odd thing was I was wanting to lick her in a lot of intimate places and it was an urge I had only read about and never had before.
I could feel the blood rush into my groin as an erection was forming and pressing against my Levi’s. She finally broke the kiss and looked down at the ever increasing erection then said “I think you will do nicely young man. I believe you are just what I have been looking for.”
Miss Bobby was a middle aged slightly overweight woman with large round pendulous breasts but still possessed an attractive alluring body. Her skin was pale and smooth and beckoned to be caressed and touched. Her hair was cut short and light in color with a little streaking. A round face with chubby cheeks and almost heart shaped pouty lips that gave promises of the sweet kisses to be had or a seductive oral interlude as they parted and slide down over a boys penis.
Not to say she would confine her attentions to only males as I was to learn she was most alive when in the company of other females and considered herself to be A-sexual, not hetero or homo or bi or as she put it she would have sex with either men, women or animals. Any one or any thing. I think she actually prefers women her own age with slightly overweight bodies similar to her own.
I later realized she chose women that could not compete with her and young students instead of men who knew no better and could be controlled easily. I was never fortunate enough to see her with an animal in person but years later did hear a few stories from one of her closest female friends who also had pictures that were almost scary of her being violated by a dog, a donkey and a small horse. All very frightening but still erotic.
Our relationship started that day and has continued. As she walked away she turned back and said “when you are ready for some more of that come and see me and maybe I will show you what to do with that rise in the front of your jeans.” I was red faced and embarrassed that she saw my lack of control. My mind was racing as I thought of the things she might want to do with my small throbbing penis.
The following week was our first time alone and my first non self induced orgasm. When I finally did approach her she just stood smiling but said nothing. I was nervous and fidgeted until I could take the silence no longer and quietly whispered “I’m ready for some more.”
Her smile turned into a contrite grin and she said “good. Follow me.” She licked her lips and looked into my eyes as if she were a predator that intended to devour me, then turned leading me down a closed hall past a couple of storage rooms and through the door into her private office at the back of the library.
When we reached her office her demeanor changed into all business. She retrieved a couple of forms she handed me and said “since you are going to be my assistant you need to fill out these forms and have your parents sign them. You will be spending your study hall class in the library each day and at least an hour most nights after school. Also there will be special projects that will take up many of your Saturday’s. Do you think your parents will agree to your committing that amount of time.”
I was at a loss what to say and felt deflated, since I was hoping for something more of an intimate nature. She saw my dilemma and said “maybe I should give you a better outline as to what your duties will be and what the benefits are. You will assist every day in the library with general help. You will in return receive help from me and a couple of others with your homework to prepare you for high school and college. You will very quickly become a straight A student and assist with weekend projects that will give you extra credit. That should please your parents.”
“Now those are the things you will tell your friends, fellow students and family when asked. I see the disappointment in your face. You are wondering what else you can expect of a more physically fulfilling nature. Come around to this side of the desk and I will help you to understand.”
As I stepped toward her she pulled me close and placed my head between her large soft breasts. My heart pounded as did my penis when I inhaled her sweet smell and felt the soft boobs press against my cheeks. She tilted my head up to her and again kissed me with her warm open mouth and tongue. The kiss lasted a couple of minutes with her pulling me close and rubbing our bodies together.
Not knowing what to do with my hands I finally put them around her and slowly guided them from her waist down to her soft butt cheeks. This caused her to intensify her deep kissing and groping of my body as she ran her hands over every part of me she could reach.
She broke the kiss and pushed me against her desk as we both gasped for breath. She said with a sly smile “lets see what we can do with this.” She had cupped her hand and pressed it against my pulsing penis as she pulled a short rolling stool over and sat down in front of me. She quickly unbuckled my belt and opened my Levi’s, pulling them down below my knees taking my undershorts with them. Her face was inches from my erect penis. It was bobbing up and down a bit with involuntary flexes.
I had only read about some of the things men and women do and only had a rudimentary idea of what was to come. She looked up so her head was tilted back and took my penis into her heart shaped mouth as she kept her eyes on mine. I groaned with the pleasure of feeling her warm wet mouth surrounding me and it was intensified by being able to see it slip into her mouth with her eyes locked on mine.
The feeling was far beyond anything I had ever experienced. My inadequate masturbation while looking at nude pictures of women had never given me this kind of sensual explosion. As she stared into my eyes she twirled her tongue around the head several times then up and down the bottom side as she slowly pushed the entire length to the back of her throat. I was rigid all over, holding as still as I could for fear of loosing control. In less than a minute I was ready to spurt my load of semen but was just managing to hold back.
Her throat was constricting around the head of my cock in a gag response that she was controlling by pulling out a little just before she retched and would then push it back down her throat again to cause another spasm. I was loosing control and she pulled it out completely to quickly say “go ahead. Shoot it all down my throat. I want you to cum in my mouth right now.”
Through this whole episode her eyes had never left mine as if she were savoring every groan and wave of pleasure I was experiencing by reading it on my face. She pushed the head of my cock down her throat again and I started to spurt with jerks of my hips that jammed it into her harder. At that age I could shoot a quarter of a cup of cum on my first climax of any day. It felt like I doubled it this time. Bobby Jo was trying to swallow it all and barley keeping up. It was all going down her throat but she was hard pressed. As I finished she managed to choke down the last few squirts and then slowly suck what was left from my still rigid cock.
She was still making eye contact as she pulled her head back saying “that was the biggest load I have ever taken from a man or boy. You could divide that up and artificially inseminate enough women to repopulate the western United States with one climax. This is going to be more fun than I had anticipated. I have a couple of lady friends who will absolutely pee their panties if I let them get their hands on you.” Needless to say both of my heads swelled with pride.
Bobbie Jo stood up and moved me around to sit on the rolling stool. She leaned against the desk where I had just stood and opened her blouse then unharnessed her large breasts. My eyes bugged out at the sight of them. I had never in my life seen real breasts. They were very large and the nipples were enormous. I wanted to touch them but was unsure of what I was allowed to do.
She pulled me closer and bent over a bit as she guided a nipple into my open mouth. It was large and hard to start with but did something that seemed impossible. It grew larger and seemed to shrivel up at the same time. As I rolled it around in my mouth and continued to nip and suck away she began to moan softly. I could tell it was very sensitive and that she enjoyed what I was doing as her whole body would shudder with pleasure every five or ten seconds.
We were still holding eye contact when I realized she had lifted her knee length pleated skirt above her waist. I broke eye contact and looked down loosing the nipple from my mouth. She was leaning on the edge of her desk with her legs spread. She wore no panties but had on some type of corset with garter belt and nylon stockings attached. Her vagina was left exposed and had short trimmed dark pubic hair with a crease down the middle that was wet and oozing clear liquid. I sat down on the low stool and stared at my first real woman vagina. The pictures I had seen were just like it but this one had my total attention. Bobbie said “see something you like?”
I didn’t know what to say so I looked up and nodded. Her face brightened and became almost evil with the lewd look she gave me. I finally said “I don’t know what to do. I have never seen one before. Can I touch it?” She grinned and said “ you better do more than just touch it. What do you want to do to it? Tell me all the things you would do if you could.” I finally said “ I really want to touch it and if I could I also want to kiss it and put my thing in it. Please tell me what I should do?”
She pulled my face up to within an inch of her partially open slit and said “ do every thing I tell you and I will give you a lesson that few males ever get in school.” She had pulled the large outer lips open with her fingers exposing another set of pink lips with a small open hole between them. This is where the clear sticky looking fluid seemed to be coming from.
I promised to follow her instructions and she began by pulling my face into the open gooey cleft. My nose and lips were inside the long warm slit. The woman smell was awesome. It was kind of earthy with a little ammonia and I could tell she had used some thing sweet and minty inside it. The taste was a pleasant mixture of salty/minty ambrosia and was making me crazy with wanting more. The aroma had brought my small dick to full attention again.
I could tell the contact of my face inside it was turning her on as more and more of the clear slippery fluid kept oozing out. I was experimenting with licking up the fluid and noticed if I licked the inside at the top of the slit she would shudder and moan longer and louder with each contact of the hard little protrusion.
She said with a moan “ I see you found my love button without any help. That is the most sensitive place on a woman’s body. Every time you touch it it sends a blast of pleasure through me.” when she said that I went to work on it with a passion. I sucked it into my mouth and rubbed it hard with my tongue and between my lips and teeth. She shook with spasms of pleasure and let out a loud groan and squeal, then pushed my head away to break contact.
“Although that feels great it is too much stimulation right now. We need to work up to that point slowly. You will bring me to climax to quickly and when doing a woman orally it should be a slow gradual build up to the orgasm. Now begin again but with a lot of licking and probing of your tongue. Oh yes that is better. It feels so good when you push your tongue as deep into me as you can. Ooh god yes!! Now just touch my little button every once in a while after your tongue licks the inside and pushes in and out of the hole a few times. Now slide you middle finger up under your chin and into the hole as far as it will go. Ooh god that is perfect. Now push your finger in and out as you lick the outer lips.”
I had slid three fingers into her hole and was working on putting my little finger and thumb in also as I concentrated my sucking and licking on the love button. “Ooh my! talking to you as you do this is making me crazy. My insides are tingling like never before. I think I’m going to cum already.”
She had grabbed the back of my head and was grinding my face into her crotch, forcing me to lick where she wanted. The only area I could lick now was centered on what she called her love button. It had grown and protruded out more than a half inch. It was swollen a bright red and throbbed when ever I touched it with my tongue or lips.
Her whole crotch area was sticky with the clear thick fluid that continued flowing out of her. I assumed it was like the semen I shot out when I came and I was trying to swallow as much of it as I could like she did when she did me earlier.
As her orgasm continued to build she started to release a thick white froth also that was almost like weak whipped cream. The inside of her vagina was getting hotter and sloppier but I never quit and soon had my entire hand inside her almost up to my wrist.
She groaned and told me to push it in as far as possible and hold it when I could go no deeper. At about two inches past my wrist I could go no deeper. Since she wanted me to hold it still instead of pushing in and out I began flexing my hand into a fist and releasing it with a slight twisting back and forth.
Her full on climax crested with a flood of juice squirting out and running down my arm before I could lick it up. The front of my shirt and both of her legs were soaked in wet globs of her sexual emissions. She was twitching and shaking with wave after wave of orgasmic clinches and she continued to moan loudly as if she ached inside.
As she finisher she became quiet and I looked up to see her eyes had rolled back and it appeared her mind was lost and in another place as she sat there rigid and trembling. She finally came back and smiled down at me saying “that was one of the best I have ever had. I can’t believe you could bring me to that height of orgasm. You are an exceptional young lover. I need to get back to work soon. Is there any thing else I can do for you before you go?”
I looked at her sheepishly and asked in a halting manner “could I put my ugh thing into your ugh thing?” She smiled and thought for a few moments then said “ maybe next time. We should have something to look forward to in our next encounter. Until then I want you to think about all the things you would like to do to me until we are together again.” With that she helped me clean up and dress then sent me on my way. Even though I washed before going back to class I could smell her essence the rest of the day and each time I looked down at my right hand I got an immediate erection as I thought about where it had been.
So started the first and most important affair of my life. My parents were delighted when I approached them with Miss Bobby’s proposal and couldn’t believe I had been selected to receive this extra help in my education. They pressed me to give even more time to my duties with her and do exactly as I was instructed. My mother was concerned that Miss Bobby Jo had just judged me on what she called my boyish good looks and she would soon discover I was not qualified for this extra help and take it away. I promised to give my all with body and soul.
Our second encounter came three days later. I had been instructed and started my new duties in the library. I was busy sorting books when a young girl walked up and gave me a note from Miss Bobby. It read [PLEASE STOP BY MY OFFICE TODAY AFTER YOUR LAST CLASS. MISS BOBBY.] My last two classes of the day were absolute agony as I contemplated what delights might be in store for me.
I was at her office door at the appointed time and anxiously knocked. I heard a slight commotion inside and a cabinet door close, then a few moments later she unlocked the door and ushered me in with her face a bit flushed. The leering look on her face almost made me shoot my wad right there as she led me over to her desk and positioned me on the stool where I had sat the last time. I wondered if she had been playing with herself as she waited for me.
As she had done before she leaned against her desk but this time she slowly removed her sweater and skirt before we began, leaving me confronted with a woman clad only in a white garter belt and nylons with a bra that had cutouts so her large nipples were protruding out and swollen in the most tantalizing manner. She sat back and spread her legs causing her large gash to open, then said “see anything you like.”
I was tongue tied and just sat there staring at the beautiful slit she had presented me and finally looked up at her face. Her eyes were open wide and twinkling with delight at the obvious lust and admiration I was showing as I gazed at her exposed private parts. “ I would love it if you would use your tongue and hand on me just as you did last time.”
I proceeded just as before, sucking and pulling at her clitoris with my teeth and lips as I diddled it with my tongue. I had also started the insertion of my right hand into her sloppy wet vagina from below my chin. I kept tilting my head up to see her face but this time her eyes were not fixed on me but were looking across the room to my right at a cabinet.
I thought I saw her wink and wiggle her tongue in that direction a few times as I continued to suck and pound away at her pussy. She was soon breathing hard and moaning as she grew nearer to orgasm. It was hard to look up again as she had her hands behind my head pulling me in. Her finish was not as spectacular as the first time but I still had her gasping for air at the end.
She sat there a few moments to compose herself and then said “last time we were together you said you had something you wanted to put somewhere.” I nodded and she continued. “ Why don’t I make it a little easier for you to do just that” and she laid back on the desk resting on her elbows as she lifted her legs. I was overwhelmed with her large shapely legs spread wide into a V with the open gaping slit staring back at me as if it were an eye.
I stepped forward and the height was just right. My small penis was pressed against the lips of her slit and I soon had it pushed all the way inside her. The slick warm wet sheath felt like heaven and she flexed it several times making it grip my penis. I began to pump in and out. My first real sex and I was soon pounding away nearing climax. It felt better than I could have imagined as I squirted my semen inside a real woman. The entire intercourse probably took no more than five minutes but was the greatest minutes of my life .
She smiled and I felt my inadequate performance amused her. She said “ well that was fun. Don’t worry, your penis with get bigger as you mature. Your not that small now. As a matter of fact you are probably larger than most young men your age” and with a twinkle she added “ we didn’t use any protection. I hope I don’t get pregnant.” Then she laughed at my shocked look and said she was kidding. Again her essence lingered on me for the rest of the day and I felt a thrill each time I got a whiff and my dick began to respond.
Bobby and I had sexual encounters daily. Many times two or three times each day where she gave me instruction in great detail. She also worked with me each day on my homework and I soon was a straight A student with a bright scholastic future in front of me.
My first special project was on a Saturday morning about five weeks after I had first met her. I had been prompted to tell my parents I was joining a group of other students and would be spending the day doing clean up after a local political event. There was such a cleanup going on but my name was only on the list of helpers and I was not present. Miss Bobby picked me up in front of the school at 9am and drove me to a friends house.
We were met at the door by a woman I recognized as another teacher from school. Miss Phillips was a bit younger than Bobby and a bit slimmer with short red hair and she wore large framed glasses as you would expect from a teacher. She also had large breast and a pale complexion. As we entered Miss Phillips was staring at me with a smirk and almost drooling. I was very uncomfortable with how she eyed me. She winked at Bobby and said you have surpassed your self with this one BJ, confirming my suspicion there had been others.
She took my hand and said “you will be the cameraman today” as she lead me over to a digital camera mounted on a tripod. She gave me instructions on how to operate it and stood close rubbing herself against me as she talked. She pinched and squeezed my butt cheeks and rubbed my crotch several times as she made sure my face came in contact with her large breasts.
I enjoyed the attention but kept getting the impression she had an evil streak in her. Not the kind that is a turn on but the kind that can be hurtful and mean. As the women began to fondle each other Miss Phillips told me to start taking pictures and then added “before you do remove all your clothing. You heard me, I said take off all your cloths now.”
She walked over and gave me a pinch on the cheek that hurt a little then glared at me until I started undressing. I removed each piece of clothing and soon stood there totally nude. I was embarrassed at being exposed in front of these women with my penis standing straight out. They were both staring at my young body. When I was exposed in front of Bobby it felt different. This was demeaning and I wondered what I had gotten myself into.
Even as weird as this situation was my penis stayed erect and I was turned on. I could tell in the short time I had been having relations with Bobby my penis size had grown. I guess having sex two or three times a day and masturbating at night was making it larger. The things we had been doing gave me an almost perpetual erection. I couldn’t get my mind off sex when I was not with Bobby and when I was that’s the first thing we did whenever possible.
As I stood there totally exposed, embarrassed and feeling very vulnerable Miss Phillips walked around me eying every part of my body. When she had checked me out completely she smiled and reached down, pinching the head of my penis. The tweak she gave it hurt but only increased my erection.
Miss Phillips returned to Bobby and as she sat on the couch they began kissing and touching each other. They would stop to pose for me every time one of them removed a piece of clothing or found a new item of the others body to suck or lick. In a short time both were nude except for their high heel shoes and they were taking turns sucking each others breasts. Miss Phillips wanted me to get close ups of their vagina’s.
She would pinch or squeeze sensitive parts of Bobby to make her jump and squeal with the pain. It would appear she was the dominant one and in charge but I finally decided Bobby was really in charge. She like to be hurt and made to do things that were degrading but I felt she was really in command which helped to relieve some of my apprehension about being around Miss Phillips.
Miss Phillips made her kiss her feet and suck her toes then had her lay on her back on the floor while she squatted over her face and had her lick her vagina and asshole. She made threats about peeing in her mouth as she ground her pussy into her face while twisting one of her breasts in what looked to be a very painful manner. The threat of being urinated on seemed to really excite Bobby.
I had repositioned the camera and was getting very good close up shots of the whole thing. Bobby was so turned on that Miss Phillips leaned forward in a sixty nine position laying on top of her so they could lick each others pussy’s. They were soon both involved in a squirming snake like orgasm with arms, legs and heads gyrating everywhere. As they finished Bobby got her wish when Miss Phillips lifted her pelvis and let loose a stream of piss right into her face.
Bobby was a little shocked and came up spitting and coughing. At first she appeared to be angry but soon burst into laughter as she called Miss Phillips a filthy bitch. Then they both began laughing hysterically between gasps of air as they began to recover from the orgasm. I was a little lost at what the joke was and stood there with a puzzled look on my face which made them laugh all the harder.
Miss Phillips got an evil look in her eyes and turned to Bobby saying lets show him what the joke is. They both stood up and each grabbed me by an arm, pulling me into a back bedroom. From there we entered a large master bath with a large round tub. I was made to sit in the center as both women stood over me. Each was standing on one leg with the other up on the tub rim. Bobby was pulling her pussy lips apart and was first to let loose a stream of hot piss. I was looking up at the lovely slit I had come to adore so much when I got the first blast full in the face. My eyes burned and I ducked my head but she continued to empty her bladder on me.
Miss Phillips was holding her vagina lips open also and managed a weak stream that quickly subsided. Thy both began the crazy laughter again and sat on the edge of the tub. Bobby said “now you are in for a real treat Portia. My little friend here is going to give you the best eating out you have ever had from a male.”
Miss Phillips was sitting back leaning into a corner on the edge of the large tub with her legs spread and her heels propped up on the edges. Bobby pushed me over between Miss Phillips legs and guided my face into her open waiting cunt. I began giving her the best tongue work out I could muster. Bobby had squatted down behind me and was pushing my face into the open crotch and began to whisper in my ear.
“When she gets real worked up I’m going to stand up and hold her in the corner. When I do I want you to do exactly what you did to me the first time we were together. As soon as you do she will try to stop you but I want you to continue. You will have to force it quite a bit as she is much tighter than I am but I don’t want you to stop for anything no matter what.”
I nodded my head and Miss Phillips was already getting excited. She was moaning and making sounds that said she was really having fun. Bobby tapped me on the shoulder and stood up. She was standing with her legs on each side of me. She leaned forward putting her knees so Miss Phillip could not close her legs, then put her hands against her shoulders. Miss Phillips was pinned into the corner and could not move.
I already had two fingers in her wet vagina below my chin and could tell she was very tight. When I inserted the third finger she began to struggle and yell for us to stop. Bobby leaned into her and covered her mouth with her own to cut off her words of protest. I proceeded to insert the fourth finger with great difficulty, thinking there was no way I could get my whole hand into her as I had with Bobby. She was struggling against us both but unable to get free so I kept up the pressure of insertion.
I was enjoying violating her even though I knew she might later retaliate. I think what made it more fun for me was that she enjoyed hurting others and it seemed like payback she deserved. I had moved my head back against Bobby’s crotch and was enjoying seeing my hand partially inside Miss Phillips. Her vagina was stretched to the point of tearing and she was whimpering in pain but Bobby kept their mouths glued together.
Bobby was turned on also as she rubbed her crotch against the back of my head to massage her crotch area. I renewed my assault by repositioning my weight to apply more pressure. I gave it one last hard push and my whole hand entered her up to and just past the wrist. She screamed and went from totally rigid to limp. I was afraid we had killed her but could see she was still breathing. I could feel the pumping of her heart through the walls of her vagina.
Bobby stepped back and said “don’t worry, she has just passed out. We have done the one thing she has feared most. She has never let me put anything larger than my finger inside her. She has some kind of phobia about vaginal penetration. I think it is a physiological problem from her childhood. I have wanted to do something like this since the first time we were together but every time I have tried she would go crazy and physically overpower me.”
Miss Phillips was coming around and at first was disoriented not knowing what had happened. Then she looked down to see me kneeling between her legs with my hand still firmly embedded in her pussy up to my wrist. Her eyes got big and tears ran down her cheeks but she remained quiet and just stared at the sight as if it were overwhelming and she didn’t want to comprehend what was happening.
Bobby was right behind me and whispered to me “time to start giving Miss Philips her first fist fucking.” She said to start out slow but keep putting pressure on to insert my arm further. I followed her instructions and in a few minutes was managing to increase the depth of the strokes. After my hand was past the initial entrance I kept I kept it balled in a fist so it would go deeper and she was soon reluctantly responding.
The pain of my invasion was apparent on her face but the pleasure it was bringing her was what she craved right now. Within ten minutes she was in the midst of the most violent orgasm I have ever encountered. It was an experience I have never seen repeated as she thrashed around and screamed through the whole experience. She cried and moaned when she finished and begged us to release her.
When I looked up at Bobby her face shown a look of satisfaction and a bit of disgust at Miss Philips lack of control. After I extracted my arm from her Bobby helped me out of the tub and assisted in washing off the gunk that clung to me. We dressed and soon left without saying anything to Miss Philips or even checking on her. I could hear her sobbing as we went out the front door. I went home that day without any sexual release and was unsure what had happened.
Miss Bobby avoided me for over a week. When I would approach her she made excuses for not seeing me but said things would be back to normal soon. I was concerned I had displeased her and so just kept making myself available without questions as I didn’t want to mess up the best thing going in my life. I saw Miss Philips in the hall several times but when she saw me she would scurry away before I was in speaking distance. What could I have said anyway, gee your pussy sure is tight or can I give you a hand.
A little over a week later the female student who had given me the note and also worked in the library told me Miss Bobby wanted to see me in her office in one hour. I was elated that she finally might resume our relationship so hung around waiting to see her.
When I knocked at her door an hour later and was bade enter she was sitting at her desk with a sly smile on her face. Before I stepped forward I noticed what appeared to be the toes of someones shoes in the small gap under her desk. As she had done on a few other occasions I was told to lock the door and stand in front of the desk for inspection. Wanting very much to please her I did exactly as instructed. I knew what was to follow as she had me do this twice before.
She said “now, unbutton and unzip your trousers.” I did as instructed and pushed my Levi’s and undershorts down to my knees as I knew this was the next step leaving myself exposed. “Now stroke your penis slowly. Oh yes that’s just right. Just keep your hand going up and down slowly. I want to see you shoot a load of sperm on the top of my desk.”
She had lifted her sweater to reveal her large breasts and pulled them out over the top of her bra where she began pulling and tweaking the nipples. I saw she was scooted down in her chair with her lower body hidden from my sight under the desk. Her eyes were glazed over and her breathing was a bit erratic as if she were approaching and orgasm.
All of a sudden it dawned on me, someone was below her desk giving her the oral stimulation I so loved give. I never let on I suspected. As we had done before I kept on masturbating as she became more excited and the thought of someone licking and sucking her delicious pussy added to my masturbatory mental fantasy. I was soon on the verge of squirting and she began coaxing me on.
“Oh yes make the strokes long and slow. Pinch behind the head and make it bigger. I love it when the head gets dark red and angry looking. Don’t cum yet. Stop stroking for a few seconds until your orgasm subsides. Just squeeze the shaft and hold it for a few seconds longer. Oh oh oh. Now pump it hard and cum for me baby. Yes stroke it. Oh god I’m going to cum.”
Her hands went under the desk. She was caught up in the throws of orgasm and was writhing around in rapture. I had started to cum and the first spurts went all the way across the desk and landed on her exposed belly in two large blobs that ran down. The following five or six squirts landed on the desk top in large puddles on the shiny wood surface. The last dribbles hit the edge just in front of me and ran off in long strings down to the floor.
Bobby was coming down off the climax high and smiling up at me with a lazy spent look and scooped up the blobs of cum on her belly then deftly sucked it off her finger as she said “I have something important I need to take care of. Why don’t you put that beautiful cock of yours away and go back out to the library and finish up your assignment. I will talk to you later after school.”
Wondering who was under the desk, I did as she told me except near the end of the hall I slipped into a supply closet, leaving the door open a crack so I had a view of anyone leaving her office. About ten minutes later the girl who had given me the message earlier stepped out and leaned against the door as she closed it. After checking the hall and determining she was alone she pressed her hand into her crotch and massaged the area as if she was either in pain or needed of relief. She tilted her head back and began running her hand up and down what I knew was her small vagina.
She continued for about twenty seconds and realized she might be caught so she straightened her self up and walked down the hall unsteadily toward me. On a whim as she got to the storage closet I opened it to confront her. Her eyes opened wide as I stepped out and she stood not knowing what to do. With a wave I motioned for her to enter the closet and reluctantly she did as I said “your name is Sarah isn’t it.” She nodded yes as I closed and locked the door behind us.
The room was dark so I flipped on the low watt light so I could see her and said “I know what you were just doing under Miss Bobby’s desk.” She flushed bright crimson and started to leave. I blocked her way and she said “well I know what you were just doing also, so you better not say anything to any one.”
I smiled and asked how long she and Miss Bobby had been fooling around. She stammered “we ugh started about six months ago and I was there the other two times she had you play with yourself and also I was in the cabinet watching when you put your hand in her then had intercourse.” I blushed a little and asked if she was a lesbian and she said sheepishly “no! I’m not gay. Miss Bobby caught me doing something in that little back bathroom a long time ago and then started making me perform oral sex on her when she wants. I kind of figured it was the same with you.”
I asked “when you left just now in the hall you looked like you were upset or in pain?” She replied reluctantly “some times when she has me go down on her I get really turned on. Especially the times when she has made you play with yourself in front of the desk. I asked if I could join the two of you some time but she just said no. After you leave she makes me lay on the desk and licks me down there until I’m on the edge of an orgasm. When I get close she stops and says when I beg enough she might let me finish. It’s driving me crazy. I don’t know what to do about it. I usually go the the girls bathroom and try to finish myself by hand but it never seems to be enough.”
I said “would you let me see if I can help you. I have just started to learn how to please a woman and would like to see if I could make you climax.” she swelled with pride at being called a woman as I reached forward and pressed my hand into her crotch like she had done at the door and could feel that she had no panties on underneath the thin dress she wore. I looked at her with a questioning expression and she said “sometimes when she makes me come into her office she takes my panties and keeps them. My mother is getting upset and asking questions. I told her someone steals them out of my locker when I shower after P.E. I’m afraid she is going to call the school and complain.
Sarah’s body was thin and without the curves ones see’s in a woman. She had nothing but small buds on her chest but they looked erect and excited as they pressed through the thin material. Her hair was short and she had an elfin or pixie look to her with large eyes and small cute features. She reminded me of a half starved waif out of some painting I had seen somewhere.
I lifted her dress and was sliding my finger up and down her slit. She gasped with the pleasure it brought. I asked “is it all right if I try?” and she readily accepted but then added “only if you will take your thing out so I can see it while you do me.” I removed my penis and stroked it a couple of times so she could see and took her small hand to grasp it. She smiled in wonder as she gripped it and I flexed it giving her a surprise. We stroked each other for a few minutes enjoying the feel of each others sexual parts and I kissed her as Miss Bobby had taught me with our tongues entwined and plunging in and out of our mouths.
I knelt in front of her and while holding her dress up began to lick her small sparsely fuzzed vagina. She responded by hooking the heel of one shoe up on a shelf behind her opening her tiny slit slightly giving me easy tongue access to her sweet young insides.
I knew nothing about virgins or whether she was one and slid my finger into the tight wet canal. She sucked in air with a hiss and was soon breathing hard. I continued to finger fuck her and ravish her clitoris with my tongue and teeth. As the orgasm was building she said “please don’t put your whole hand inside me like you did to Bobby. I would love to try it someday but I think it would kill me now.” She was soon deep into a climax that made her buck her pelvis into my face. I stayed with her gyrations and was still sucking her pussy when she finished.
As she eased down I told her I didn’t have a rubber but still wanted to put my penis in her. She responded “ I have never had sex before but it is all I have thought about since I saw you do it to her. I don’t know if I can take anything that big inside me but would love to try and don’t worry you won’t need a rubber because I won’t get pregnant.”
I didn’t understand why she wouldn’t get pregnant but was more interested in getting inside her at that moment. The floor wasn’t that clean so I asked if it was alright to try it standing up. All she said was “yes please and hurry I can hardly wait.” There was an old desk in the corner that she moved to and after leaning back against it lifted her dress exposing her lower body just as Bobby had except she had one leg up on a box next to her to open her crotch for me.
I used my finger again plunging it in and out of her tight pussy to restart the juices flowing then rubbed them on my cock for lubrication. The head was pressed into her slit but it seemed much to large for her. I was probing in hopes something would give when she said “your going to have to force it. The only thing I have had inside me is Miss Bobby’s finger and a slender candle I have at home. I think your penis is about four times bigger around than the candle. Maybe if you do it quick it won’t hurt as bad.”
I wiggled it around a few times to get positioned and then plunged in hard. She squealed as the head forced past the tight entrance and I saw I had almost half of it in her. It was tight and she swooned a bit as we both waited for her pain to subside. After about thirty seconds .she told me “start pumping it in and out a bit. I think I can take it. Oh god that feels good even though it hurts.” She looked down and saw I had only about half of it in her and said “ I can’t believe there is more. It feels like you shoved a baseball bat in me. I’m so filled up I feel like I’m going to split open any minute.
The tight sheath than enveloped was wonderful. The pressure that was squeezing me was beyond belief. It tried to stop me from pushing in farther and then tried to hold me as I pulled out. After a couple dozen strokes I was making headway. I had all but the last two inches in her and gained a bit on every thrust. Her eyes were closed as she endured the assault with a quick intake of breath each time I plunged further in. I felt the head of my dick make contact with what ever is at the end of a woman’s pussy. The first time I bumped it she jumped and cried out a bit so I stopped to just let her get used to feel.
Soon her breathing slowed and she urged me to continue. I started to pump again, going slow and doing the longest strokes I could. The feel of truly filling and fucking someone was quickly bringing me to the edge of climax. In the back of my mind I was worried about shooting a load in her so asked if she was sure it was alright. She replied in a breathless voice “don’t worry. It’s safe. Please keep going it feels great. I think I’m going to cum again. Oh yes! Oh god I’m cumming!! Yes! Yes! Yes!
With her words and moans I was pounding away again and soon squirting a huge load deep inside her. Her hips were meeting my every thrust and we both were soon totally depleted and holding each other in a tight embrace. As we held one another quietly each of us would occasionally have a sex organ flex or spasm that would cause the other to do the same. With me still inside her those sexual twitches were indescribable. This went on for at least ten minutes making for one of the most intimate and sensual times I can remember.
I found rags to wipe up the mess I had made of her pussy and delighted in being able to lightly dab away at her small vagina. We straightened up enough to get to a restrooms and finish our cleanup. Both of us left after school that day without returning to the library.
We met at a small fast food place where kids hangout near the school to talk over what had happened. My first question was about why we didn’t need to use a rubber. She explained that when she started having a period she had some trouble getting regulated (what ever that meant) so her older sister told her if she played it up a lot her mother would get her on the pill. She did and had been using birth control for over six months. She then told me Doctors found that birth control pills help to regulate young women. My first response was “so this means you and I can have sex anytime we want.” She quickly replied “yes we can and I hope that is often because that was the best feeling I have ever had and I want to have it everyday.”
We both continued to participate in the sexcapades of Miss Bobby through junior high and never let on we even knew each other. We also watched as she recruited others to play out her fantasies. I stopped in to use Bobby all the way through high school and college. She was not as interested in me as I became an adult but would still let fuck her any time and any way I wanted. The last time I screwed her she was over sixty and still loved it.
Sarah and I continued our affair and still do. It has always been as friends and we still get together often. We found many places in our neighborhoods to secretly fulfill our desires. I had a tree house that no one used any more and she had a playhouse her father had built for her and her sister. We found many families have these abandoned buildings that we could use if we were careful. We explored the world of sex together and used a copy of the Kama-Sutra and every porn magazine I could get to find new experiences and positions. Miss Bobby set us both on the road to full sex lives and I will always be grateful.
Writing this has wet my appetite again so I think I will call and see if Sarah can get away for a couple of days to continue our experiments.
