My High School Principal Ch. 01bywalterio©
My high school principal was Helen Eisenhower a very distinguished and professional looking lady. She was about 5'7", 130 pounds with a lovely figure. Her hair was blond turning to gray, which she wore tied up in a bun. She always wore tailored suits with the skirt cut right at the knee and looked very regal almost like the Duchess of York. Helen was 50 years old and her presence and stature demanded respect.
My name is Walt and I am the Senior Class President. I am also one of the schools top student athletes and captain of the football team. I am 6'0", 200 pounds, light brown hair and blue eyes. My physique is sculptured because of sports activity and I have been blessed with a very impressive dick that is 9" long around about 6" around. I know because I can grip my tennis racket but cannot grip my cock with my fingers touching the heel of my hand.
I have been dating a cute senior girl named Karen, a cute blond haired cheerleader who can't get enough of my cock. Karen has a killer ass and has learned to take my cock all the way into her asshole. She loves our sex bouts when we 69 first with both of us coming, Karen usually several times on my face while I fill her throat with my jizm. Then we move to missionary style or with Karen's legs thrown over my shoulders so I can fuck the daylights out of her. Finally I roll her exhausted and seemingly lifeless figure over on her knees and fuck her ass thoroughly, filling it with my third load of cum.
This particular day I was to meet with Helen Eisenhower as I routinely do on Tuesday afternoons as the School's Student President. When I arrived at her office there was no one around. The secretary normally there was not to be found, so I took a seat in the waiting area outside her office. I waited about 10 minutes past of scheduled meeting time and decided to see if she was in her office. I walked into her office and she was not there. I thought to check her desk calendar to see if she still had the appointment scheduled and as I was reading it I faintly heard voices coming from an adjoining room.
I moved closer to the door leading to the principal's conference room to try and hear better. It was still very faint so I picked up a drinking glass and held it to the door with my ear pressed up against it. The voices were much clearer then and seemed more like moans and groans. I tired the door handle and it was open, so I pushed it open a crack and the sight before me was incredible. Here was our distinguished looking principal lying on her back on the conference table. She had shed her suit jacket and her suit skirt was pushed up to her waist. She still wore her stockings and garter belt but her panties had been removed. Standing between her legs with his trousers and boxer shorts down around his ankles was my Gym teacher and coach, Mr. Scanlon. He was fucking her pussy for all he was worth.
"Oh God, fuck me and make me cum", yelled Ms. Eisenhower. "Yes, yes, yes", she continued. Then Mr. Scanlon announced that he was cumming and Helen pleaded with him not to cum until she had. "Please Mike don't cum yet, make me cum, make me cum", she begged. But her pleas were to no avail and the coach came in the principal's cunt leaving her unfulfilled. "Damn you I asked you to wait for me", she said. "Fuck you, you ungrateful bitch you are lucky I come in here to fuck you at all. If it wasn't for me you wouldn't get any cock", replied the coach.
The coach pulled his dick out of her and proceeded to wipe it off on her panties. I was surprised to see how small the coach's cock was in comparison to mine and other students. "I hate it when you wipe your dick on my panties, you are so gross and inconsiderate", she told him. "Fuck you, you love it", the coach said as he finished getting dressed. Then he left the room through an entrance that was well disguised as not being a door. "Damn him", Helen said as he left and then she began to finger her pussy trying to get herself off quickly. She clearly had forgotten about our scheduled meeting. This was the first time I had seen anyone else fuck and it was kind of a turn-on. I had a raging hard-on pushing up through my trousers. I decided to go for it.
I walked into the room and quietly closed and locked the door behind me. As I approached Helen I noticed that she had her eyes closed as she finger fucked herself. I lowered my trousers and briefs and walked over to her. "Let me help with that Ms Eisenhower," I offered and a startled Helen sat up quickly. "What are you doing here, how did you get in, Oh my God!" she carried on. "We had a meeting scheduled for today"; I answered noticing that her gaze was fixed on my erect 9" cock. "I thought I cancelled that, oh my God what you must think of me", she went on. "Relax, this will be our secret and I want to give you what that asshole Coach Scanlon didn't", I assured her.
I moved between her thighs and placed my cock at the entrance to her cunt. She shivered in anticipation. I eased her back down on the table and proceeded to feed my thick cock to her. "Oh we mustn't, we shouldn't, it is not right and then oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", she cried. I slid in and out of her pussy slowly allowing her to adjust to my size and continued to go deeper with each thrust until I was buried balls deep in her pussy. "Oh my I have never been so full of cock, fuck me, make me cum, make it last forever", she cried out.
I pounded her pussy making sure that my cock was in constant contact with her clit. Ms. Eisenhower had multiple orgasms as I fucked her. I pulled her blouse out of her skirt and pushed it up over her bra. Then I reached under her and unhooked the bra and pushed it up over her tits. She had pretty firm little tits with rock hard nipples that extended a ½ inch. I twirled the nipples in my fingers and then leaned over taking one then the other in my mouth. She went wild telling me. "Suck my tits, suck my nipples, fuck me good!"
I could feel my balls start to tighten and I knew it wouldn't be long before I filled her pussy with my cum. Helen stiffened and then had a violent orgasm and she yelled, "Hold me, please hold me, I'm cummmming!" I reached around behind her and pulled her toward me as she shook and trembled through her intense orgasm. As she was cumming so was I and I fired a barrage of cum into her pussy. As she started to recover I laid her back down on the table and slowly fucked her as my cock softened. My cock was swimming in her cunt; there was so much jizm in there mingling with her own juices.
"Are you okay, Ms. Eisenhower?" I asked her. She smiled at me and said,"I think you should call me Helen from now on. My God, I have never cum like that in my life, nor have I ever had anyone cum that much in me before." She looked down at my soft cock and took it in her hand, "My you are a big boy", she said. "I think we should schedule our meetings for Tuesday evening at my house from now on", she continued. "Fine with me", I replied and we agreed to meet next week.
We both cleaned up and got dressed. I looked at her again and she looked just as professional and regal as ever. You would never know that she had just been royally fucked and filled with dick juice.
The Second Meeting
My girlfriend Karen and I had fucked like rabbits on Friday, Saturday and Sunday but I made sure to rest Monday. By the time Tuesday evening rolled around I was ready to fuck Helen Eisenhower's brains out. As I headed over to her house I tried to anticipate the night ahead. I knew that I wanted us in bed naked and I wanted a shot at her ass. I wondered if she had ever been fucked in the ass. The idea of fucking this regal looking high school principal in the ass gave me a roaring erection.
When I arrived at Helen's house she invited me in and made me feel quite welcome. She was wearing a full-length robe with matching slippers and looked very beautiful. After some chitchat, Helen showed me her home. Her bedroom was exquisite complete with a huge Jacuzzi tub in the master bath. As she was showing me the room I moved up behind her and put my arms around her waist. I pulled her back toward me and nuzzled her neck and ears. She trembled slightly in my arms as I ran my hands up over her tits and pressed my hard cock against her ass cheeks.
I moved her over to the bed and slipped the robe of her shoulders, she was completely naked under her robe. Helen then lay back on the bed as I shed my clothes as fast as I could. I surprised her by sliding my tongue up her legs and kissing the inside of her thighs. I licked the outer folds of her cunt and she moaned softly. "Are you sure you want to do that?" she asked me shyly. "Absolutely, I have been looking forward to this for a week", I told her.
I began to eat Helen's pussy and drove her crazy. "Turn around and give me your cock, I want to eat you too!" she said. We moved into a 69 position on our sides and then Helen rolled over on top of me. She began to deep throat me and it was obvious that she had sucked cock before. I licked her pussy and penetrated it with my tongue. I held her by her gorgeous ass cheeks and marveled at how firm she was for a 50 year-old. After awhile I started to finger her pussy and then her asshole. It took her a little bit to get used to my finger in her ass and it became clear to me that she was surely an anal virgin.
Helen had several mild orgasms before another shuddering one. As she trembled and shook through her orgasm, I imbedded my entire middle finger in her asshole and at the same time filled her mouth with a gallon of cum. Helen swallowed as much as she could and then began to lick up the remainder off of my thighs and balls. She continued to suck me and fondled my big balls as well as I gently nibbled on her clit and fingered her asshole.
We were both getting aroused again when Helen asked, "Would you fuck me now, please!" She rolled over on her back and opened her legs as I moved in to position. "With pleasure my lady", I responded. She looked like a queen about to be ravaged by a knight with his powerful lance. I have had my share of girls and Karen is a beauty, but I had never been so turned on as I was tonight. Helen and I fucked for hours as I held off coming for as long as I could. I wanted to pleasure her all night if possible. Finally Helen said, "Please stop, I have to rest. I have never been fucked so thoroughly in my life. I want this to go on forever but I need a rest. I am not sure I can cum any more."
Helen ran a bath for us and we soaked in the jets of the Jacuzzi tub. She had added some bath gel and salts, which were very refreshing. Helen leaned back against me and I reached around and fondled her tits lovingly. She was in ecstasy and totally relaxed. After the bath we dried each other off with huge terry cloth towels and as she was drying me, my cock was at full attention. "Does that thing ever go down", she asked as she dried it tenderly. "Not as long as I am around you", I said cupping her ass.
I offered Helen a massage to which she enthusiastically agreed and gave me her favorite body oil. She lay on her stomach but I rolled her over and said, "Front first". I started at her feet and worked my way her legs and thighs but I did not touch her pussy. Then I moved my hands up to tits and twirled her delicious nubs in my fingers. I worked my hands back down her torso and this time I work her pussy and fingered her gently as well. She had another small orgasm just from being touched. "Time for the other side", I told her rolling her onto her stomach. I marveled at her soft flawless skin and shapely ass.
This time I started with her shoulders and worked my way down to her ass, thighs and legs. She was so relaxed I felt that she might fall asleep. I paid special attention to her ass and placed a well-oiled finger in her bunghole. My finger was so slick and she was so relaxed that it slid in easily. I continued to massage her shapely beautiful ass and finger her hole. I added a second finger and although it was much snugger Helen didn't complain. I pulled her up by her hips until her curvy ass was in the air and she lay with her head to one side on the bed. She was almost crooning as I continued to finger her asshole and then began to finger her pussy as well.
I removed my fingers and eased my engorged cock into her pussy. I began to fuck her slowly and then added first one then two fingers back in her asshole. Helen was on the verge on an uncontrollable orgasm and as she began to thrust and shake, I took advantage of her state and slid my cock from her cunt to her asshole. I managed to get the head in past the spincture and then let Helen do the rest. As she bucked and shuddered with an intense orgasm she impaled her ass on my cock. Only when she started to come back to earth did she realize that about half of my cock was in her ass.
"Oh my God you are in my ass. I have never done this", she said in a panic. "Relax", I told her "I would never hurt you, trust me, you will learn to like this", I reassured her. I continued to ease more of my cock into her ass feeding her a little at a time. It seemed like hours before I was all the way in and began to slowly fuck her. I played with her tits with one hand and her pussy with the other. Soon I had a smooth rhythm going and I was sawing in and out of her ass easily. I felt my balls tighten just before I blasted an enormous load of cum into her asshole. I had never come so much and my cock felt like it was twice its size in her ass.
My cum was backing up out of her asshole and running down over her pussy between her legs. My dick softened and I eased it out of her asshole with an audible popping sound. I collapsed on the bed and Helen lay next to me handling my softening cock. She blew me away when she slid down and took my cock in her mouth. As she lovingly cleaned my cock with her mouth she kept repeating, "Thank you; oh thank you, thank you".
It was quite a sight to see this sophisticated lady, this regal beautiful woman, sucking on the very cock that just fucked her in the ass. We fell asleep and the last thing I remember was my cock in her mouth.
The Tuesday Meetings Continue
For the next several weeks I continued to meet Helen at her home Tuesday evenings. Our routine stayed pretty much the same with us eating each other, fucking her pussy and fucking her ass. I learned that Helen had a small collection of vibrators and dildos that she had ordered through the mail. She started with the smooth battery operated vibrators and then got bolder moving up to the realistic looking dildo.
We added some variation to our sex routines. Sometimes when I would be eating her I would push a dildo into her pussy. Other times when we were in a 69 position I inserted a small vibrator in her asshole. This really accelerated her orgasms. I began to stick dildos and vibrators in her ass while I was fucking her missionary style. Helen really enjoyed the double penetration. However in spite of all this debauchery, Helen always looked sophisticated and regal. She loved sex in a passionate but tender way, something she was not getting before our affair.
One time when we were in a 69 position I placed a dildo in her cunt and another one in her asshole as my cock filled her mouth. I nibbled on her clit as I worked the two dildos to perfection bringing her to multiple orgasms until I filled her mouth with my seed. She went wild and drenched my face with her own juices.
Afterward we lay in each other's arms and as I stroked her sensuous tits I asked her, "Have you ever had sex with more than one person at the same time". "No I haven't", she said, "But recently I have been thinking about it, particularly since you started penetrating my other holes with those dildos". "I have actually fantasized that there were two other virile young men such as yourself filling my holes", she added. "Would you be interested in doing that", I asked excitedly. "I think so but I really have to think about it and be assured that if I did, that the two added partners would be as discrete as you", she replied. "Let's give it some more time and I will think about it. In the meantime, I am ready for you to fuck my pussy until I can't cum anymore"; she said as she rolled over on her back and opened her arms and legs to receive me.
My large erect cock slid right in to the hilt and we fucked like crazy for the next several hours. I finished up in her ass again as we had before but this time I was able to stay hard and fucked her ass twice without removing my cock, filling her asshole with two generous loads of cum.
Tuesdays are not enough
Helen got to the point where she could not wait a whole week between sex encounters. My cock was on her mind all the time and she found herself masturbating frequently with her dildos. We agreed to meet Thursday in addition to Tuesday evenings and they were just as intense.
Helen began calling me into her office on Monday, Wednesday and Fridays. We would adjourn to the conference room and she would slip off her skirt and panties, I would drop my trousers and briefs and fuck her on the conference table. Sometimes if we were in a hurry she would just raise her skirt and lower her panties and I would either eat her pussy or fuck her. Once I even fucked her in the ass with her bent over the conference table with her skirt pushed up to her waist and her panties dangling around her ankles. It was the most erotic sight I ever had with her, to see this sophisticated lady dressed all prim and proper bent over the table with my huge cock fucking her asshole. I thought to myself, what the reaction of the School Board would be if they walked in and saw the High School Principal getting "corn holed" by a student. Helen continued to get more demanding and I made up my mind that it was time for her to have additional sex partners.
One afternoon we were having a high school assembly in the auditorium and Helen Eisenhower was presenting to the student body. She was impeccably dressed in one of her best-tailored suits. As she moved around on the stage her body language displayed confidence and sophistication. She moved with a grace and a kind of sexual aura found in Royalty. As I watched her it was hard for me to believe that this was the same woman that had taken my cock and dick juice in all of her holes the night before. No one watching her would ever guess that she was capable of so much raw sexual passion.
I was seated with two other jocks, Ken and Jay who were also my best friends. I heard Ken say almost under his breath, "Man that woman is special I would love to fuck her". To which Jay responded, "Me too, but that's playing with fire a good way to get yourself expelled and fuck up your chance for a scholarship". I smiled and thought if they only knew.
I enjoyed listening to these guys during the rest of the presentation as they were fascinated with Helen and were sporting obvious erections. I decided then to include them in my plan and how to launch it to protect everyone's integrity, particularly Helen's.
The three of us went out that night to get a few pops before we hooked up with our cheerleader girl friends. When I told the guys about Helen and I at first they didn't believe me but then understood why I had no reason to make it up. We all had all the pussy we could handle so why fabricate any stories. When I asked them if they still wanted to fuck her, they both chimed in,"Hell yes!" So then I told them how we would set it up and what time they should arrive at Helen's house this Thursday evening. I knew that Ken and Jay were well hung although not as big as I was, they would be very satisfactory for Helen.
Our dates eventually showed up that night and the three of us guys were extremely horny from all of my talk about Helen and their anticipation of what was to come. It was a sex filled night for us and our girls, the girls didn't know what hit them or what brought it on but they didn't complain.