My Sister Shows off Her Cheerleading Skills Pt III

It was only a week before Christmas vacation, my grades were better than usual and I was feeling real complacent about my academic life at the University. I was therefore surprised to see a note in my box to see Mrs. Weissman, my studies coordinator at Henderson Hall right after my last class. I could not think of anything I had done recently that might have come to light. My relationship with Madison was ended shortly after Thanksgiving. She was boning a Dentist who was giving her some free dental care and a lot more in her mouth than dental equipment. I bet she was the best blow job expert on campus with exceptionally white and sparkling teeth.

Jason told me it was for the best because she was too much into taking it up the ass. Now, Jason was kind of fixated on butt fucking, so I figure he had her number real good. It was kind of a shame because I had developed a bit of a liking for Madison and suspected I would have stayed with her for a long time if she had any inclination in that direction. I watched her from a distance, not stalking or anything like that, but I knew I was ready to be her puppy dog if she crooked her finger at me.

Mrs. Weissman was an old married woman and her husband was a tenured professor in the English studies department. When I say she is old that may be a little misleading. She is in her mid-thirties and is kind of a knockout with a nice package up top and a tight little ass that could have been on a female 15 years younger. I thought I might have pissed her off by peeking up her skirt in class from my vantage point in the first row. She didn’t report me and I tended to avoid her except at our scheduled meetings. I once helped her when her heel got stuck in a grate behind the gym. I have to confess my face was only inches from her sweet smelling snatch as I held her tiny little ankle in my hands. I hope she didn’t see the huge erection I had to take with me into the gym class. Then, she was a witness to Madison giving me the sloppiest blow job of my life in the movie right before me and Madison broke up. I was so embarrassed for her to see the cum stains all over my shirt and trousers after the lights went up.

I was a little nervous about meeting Mrs. Weissman because I was afraid she would think I was a real horn toad to want to see her little pussy and went around getting blow jobs in public places. The truth was I had only had sex with 4 girls other than my little sis Sue Anne. My friend Jason, on the other hand, had already had sex with almost 50 females of all types and ages. He even had screwed the minister’s kindly little wife after a bingo game in the church basement. I was watching from behind the door of the men’s room and he pooched her bottom like she was a 16 year old high school student.

Jason and I were almost 20 now and my kid sister Sue Anne was 17. I started to give it to my sister big time after she showed me what she could do with Jason in our playroom basement. I think it was the noises she made when he was ass fucking her that made me decide to be more than just a brother to her. Sue Anne was always ready to take it in her mouth, her pussy and even deep into her tight little ass. She had apparently been practicing her oral skills in high school since after her 16 th birthday party and her tongue was the most skillful I ever had the pleasure of being licked by.

This past summer I had taken her ass every night. We were very discreet, she restrained her vocal outbursts and I slid in slowly and quietly for a long time each night as we lay under the blanket on top of my bed. When she started to climax, I usually put my hand over her mouth to remind her to make it a silent orgasm. I generally just made a little gentle moaning sound as my creamy cum oozed into her pretty little ass.

The good thing was we never argued anymore and she would do little things for me like butter my toast or save the last ice cream pop for me. I found I was getting more into her like wanting to sniff her dirty panties and giving her a nice back massage or a foot rub when nobody was looking. She would purr like a kitten when I paid attention to her like that and I know she really loved it.

She had a “boyfriend” in her class. I knew she was just playing him and using him to get some things she wanted. The most she gave him was feels of her boobs and sometimes letting him put his finger in her poop chute or touch her on the outside of her vagina. She did a lot of public kissing with him and I think she did it to keep the other pussy hounds at bay.

My thoughts were of Sue Anne and the upcoming Christmas holidays when we could be together again for two long weeks.

I guess I was daydreaming a little, walking into Mrs. Weissman’s office at the appointed hour. I could see her staring at me as I approached her desk. When I sat down, I realized I had a really hard erection that stuck out in a visible tent.

She must think I am a real pervert.

“Robbie, I want to let you know that next year you will be in the accelerated student program. I have selected you because of the improvement you have shown these past six months.”

“Thank you, Mrs. Weissman, I really appreciate your confidence in me.”

“Connie! Call me Connie, Robbie; you can call me Connie when we are alone like this. I could not help but notice your thing down there is all excited again. It seems whenever I see you it is trying to get out of your trousers. Are you still seeing that girl I saw you with at the movie?”

“No, Mrs. Weissman, excuse me, I mean, Connie! We broke up. I guess you could say she dumped me.”

Mrs. Weissman rose from behind the desk and leaned over it to look at my throbbing “tent”. She looked me in the eye and ran her tongue over her lips very suggestively. I had no doubt about what she was thinking. It took me only a second to expose my little guy, well, maybe at 9 inches, not too little; to her scrutiny.

She came around the desk and I could not help but drool at the sight of the tight skirt across her ass cheeks. I wanted to bury my face in her beautiful ass crack and drive my tongue deep inside her.

She took a cushion off the couch and placed it on the floor in front of my chair. When she fell to her knees between my legs, I knew she was about to put a buzz on my waiting cock. The little flicks of her pointed tongue all over my shaft and even down on my hanging balls made me start my pre-cum leaking right away. Connie licked all my liquids up with her wet tongue and swallowed it all into her thirsty mouth. I desperately wanted her to cover my shaft with her pretty lips. When she finally took me in between her beautiful lips, I shuddered with repressed emotions. My body started to shake with uncontrollable desire to impale this proud and strong woman with my cock and make her take me deep inside her core.

I could hear Connie humming and singing to herself as she stroked my firm shaft with her suctioning mouth. Her saliva began to leak out her pretty red lips along with a mixture of my pre-cum. I saw it dribbling down her chin and falling onto her bare skin between the end of her skirt and her knees. The sight was too much for me and I grabbed the back of her pretty head and jammed her face, that adorable face, up tight into my groin as my spunk began to rise and shoot into my shaft with a high level of force. My first spurt of creamy cum must have hit Connie in the back of the throat because she gagged a bit and then started to swallow with a resolute manner. When my overabundance of semen started to come out around my cock, I pulled out just before my last spurt shot out with some force onto her forehead and eyebrows and slowly dribbled down her pretty face.

She got up off her knees and went to the sink and wetted a wash cloth. She wiped her face clean and came over and cleaned my cock with her gentle hands. I saw Connie look at herself in the mirror and I thought she had a look of disgust for her slutty performance. It seemed almost impossible that this unapproachable mature woman would be on her knees to me in such a submissive manner.

I decided not to put my cock away.

She saw me get up from the chair and take off my trousers and drawers. I was naked from the waist down. My cock was still standing straight out in front of me at a slightly upward tilt.

Connie looked at me in the mirror and started to whimper like a little girl. She knew she was going to get it real good now. I could see her tremble a little in anticipation of the sex to come.

Her hands had a good grip on the sink and she was bending forward slightly into the mirror. She could see I was standing right behind her and knew I was naked from the waist down. I took hold of her skirt and pushed it up all the way to her waist.

She had on these exquisite sheer transparent pantyhose that shaped her ass cheeks into a heart-shaped target of opportunity not to be ignored. I pulled them down being careful not to damage them or appear overanxious. Now, all that stood between my pulsating cock and her wet and ready slit was a pair of flimsy thongs. They were so flimsy and so narrow that I just pushed them to one side and presented my cock against the rear of her pussy. Her hole was primed and ready. I slid right in and was captured by her throbbing vaginal walls clutching my shaft as I entered deeper and deeper into her mystery of womanhood.

Connie’s delightful ass pushed backward into my groin and muscular legs. I started to hump her wet and open pussy in a standing doggy style while we both looked into each other’s eyes in the mirror. She was so tight that I was forced to push with some force into her vagina. It was strange that a 35 year old woman would have such a tight pussy. I found out later her husband a bit of a switch hitter and he mostly penetrated her mouth and her ass for his pleasure. Most of the time he stuck it up her ass with her bent over wearing men’s clothing. She told me he would call her dirty names and spank her ass cheeks. He told her to beg him for more of his dick in her ass. She had to use a very deep and manly sounding voice when she did so.

Mrs. Weissman told me it did not bother her that much because he was always kind enough to masturbate her pussy at the same time and bring her to a satisfactory orgasm.

I was really deep inside Connie’s pussy now and my juices were struggling to flood into my shaft. She looked into my eyes in the mirror and nodded her head in assent. That was all I needed. I grabbed her sexy hips and pulled her into my cock as I shot my entire load deep into Mrs. Weissmans’s pussy. She felt my shower of sticky cream coat her insides and yelled very nasty things at me in the mirror. She spit into the mirror at my image and told me I would have to lick her asshole if I wanted any more pussy.

Actually, that sounded like an interesting proposal to me.

I couldn’t wait for our next meeting on the last day of school just before the Christmas vacation.