tagFirst TimeAnn and Me

Ann and Me

bybadboy005©

It was a hot night I remember thinking as I laid in bed next to her. Summer in Phoenix is always hot regardless how much A/C you got going on.

Going back in time I remembered when I met Ann and thinking about it more, time and ages passed away. We met in a very unusual circumstance with me being a teacher and Ann, or course being a student. Yes, it was college and I a professor but I was far from being a "dirty old man". I was a gifted student myself and soared though school very quickly gaining several academic awards and recognition, and I gained the position I held at the ripe old age of 22 years. The Subject of History having a special calling to me I took a position at the local university and directed our spirited youth though my classroom. Teaching these history lessons, I quickly discovered while this subject was something I loved it wasn't everyone's cup of tea.

In my third year teaching I came across Ann. She was a fierily red head who didn't like to take or receive any direction at all. While she was brilliant she lacked direction and motivation. I decided to take it upon myself and help her. Let me say Ann was stunning. She was 5'4 and about 110 pounds, long flowing auburn hair and the most perfect breasts, which begged to be embraced by the lips and tongue.

The summer of 1969 was a different era and the people of the sixties were free and without boundaries and Ann was a child of the times. She loved wearing the low rider bellbottom blue jeans and flowery tight fitting blouses with flowed at the cuff. Of course Ann didn't believe in wearing a bra or any underwear for that matter, because while I was teaching the class today I remembered seeing her sitting front row center wearing a short skirt, and as she moved her legs to and fro during the class a glimpse of luscious auburn hair peeked out.

Was she teasing me? I asked myself later when I got home. Could I have her? I knew about free love but being a shy man I wouldn't know where to begin. Do you just go up to her and say, "Hello, my name is Max. Do you want to fuck?"

Nevertheless I needed to try. That night while at home alone, seeing her shapely legs crossing and uncrossing in my mind, the thought of Ann was consuming my thoughts and I took my cock out and began masturbating to the memory of her auburn pubic hair and hard nipples, straining against her tight blouse. Yes, as I stroked my cock faster I knew I needed to make her mine but again, while I was smart in the classroom I was lame as hell out of it. In my entire life I only had sex with one person and that was awkward and short-lived. Cumming as I whispered Ann's name I rubbed the cum over the head of my cock enjoying the feeling. Not bad for a white guy, just over 7 ½ inches but I was getting tired of beating off. I wanted Ann so badly but again, not sounding like a broken record didn't know where to begin. Rubbing my cock head between my fingers I decided I needed to take a chance and try something new. I decided tomorrow would be the day.

The next day before class I didn't wear my usual suit and tie and tried something different. Earlier that month I received some clothes from some "hip" friends who decided I needed a change. I, of course, said thank you to them and put the clothes away in the closet, thinking at the time I would never wear them. But now I watched as I put them on. Everyone said they were cool but I didn't like them. The shirt made me feel like a pirate and the pants were way to tight for my comfort and showed a definite outline of my cock. I had no choice but to continue on with my plan regardless how uncomfortable I felt.

Class that day was uneventful and as surprised as I was my outfit fit right in with the students. As the day neared the end I asked Ann if she could stay after class and discuss (what, I didn't have a clue) some school matters with her. Smiling at me she said, "Of course."

When the class had concluded for the day and all of the other students left Ann walked suggestively up to my desk, leaned over so I could see the natural fall of her perfect breasts asked what was on my mind. Going over some lame details affecting her grade I asked what were her plans with her life.

Speaking with her about personal matters was like being in heaven. We talked about how she wanted to be involved in saving the whales or why the war was wrong. The truth was I didn't give a shit what she said I was just trying to get her to open up and spend some time with her. Agreeing with her on some of her political point and not on others I suggested we meet for drinks later that night at the local bar where several professors and students mingled after class (remember, it was 1969, not 2006 and the times were different).

Ann agreeing said she would like to have a drink with me and continue our conversation got up from her chair and I believe I saw her look down at my crotch and smile as she left. Seeing her close the classroom door behind her I noticed my cock was as hard as I was happy. I did it! I asked out Ann for a drink and she accepted. Now I just had to keep the good times going.

Before I, met at the bar I had time to get home, and clean myself up. Finding a small table in the corner I sat down and waited. A little before 8 o'clock Ann came in wearing a low cut sun dress which showed off her long luscious legs. Her hair was free and as she walked it looked like she was dancing. Motioning to her where I was at she smile at me and came to my small table.

"Hello Ann, What would you like to drink tonight?" I asked.

"Whatever your having." she replied.

Ordering the drinks we continued our conversation. While I was telling her about my college days she interrupted and suggested we leave Bar and take a walk. Quickly agreeing with her we left table and walked out of the bar and into the night. Approaching the college campus we Ann asked, "Max, do you find me sexy?"

"Yes", was all I could say as my voice caught? "You know, I kind of think you're cute and would like to get to know you a little better." Ann said as she brushed up against me. "I would like to know you better also." I replied hopping I wasn't blowing this.

"Good, lets go back to your place. I have a idea what we can do so we can better introduce ourselves." Showing Ann the fastest way back to my place I opened the door for her and showed her around.

"Do you live by yourselves or do you have a roommate?" she asked

"Just me Ann"

"Good, Sit down in this chair and I will sit across from you on the couch"

Doing as I was asked Ann told me she liked me a lot and wanted to know me better but first I had to show she something.

"What", I asked.

"That cock in your pants but before you get any ideas in your little teacher mind I just want you to know who is in charge here. I like you Max but I'm a virgin and I entail to stay a virgin, but that doesn't mean we can't play together. If your willing to not put your cock in me we can have a lot of fun and both feel good."

"Alright, what do we do first?" I asked being confused.

"Take out your cock and I will show you what you were staring at yesterday."

"Will I be able touch you?"

"Maybe, let's see how good your are first." Ann replied smiling. "Go ahead, let me see what you got."

Standing up, I slowly unbuttoned my shirt and removed my pants. Trying to fit in with the crowd I decided not to wear underwear tonight and as my fly was opened my engorged member sprang out greeting her.

Ann smiling ear to ear retuned the favor and quickly pulled her sundress over her head, standing naked in front of me. She was the most beautiful woman I have ever seen, and still to this day nobody had come close to matching her perfection. Her skin was creaming while and her nipples rosy pink, stood out begging for attention. Her body was like a perfect hourglass and between her thighs the most luscious thicket of auburn hair. I could just make out her womanhood beneath the hair. Thinking back on my history background it was visions of this men fought over.

Telling to sit down in the chair she said she wanted to watch he pleasure myself the best way I know how. In turn, she would return the favor and when we were done and she would come over and meet me in the middle of the room and then, once trust was established we could explore each other body.

Agreeing with the rules she set forth, I watched on as her hands slowly caressing her neck and slowly, very slowly moved down to her breasts, tickling her nipples slowly and pinching them. I watched on being more aroused then I could ever remember was rubbing my balls and from them following the stroke up my long shaft, rubbing the gland as I reached the top. Ann watched on and smiled approvingly. "Feels good doesn't." she asked.

"Yes" I replied as I watched her pleasure herself.

Time went on – how long I don't know but I watched as her hands found her center and began stroking it. Ann didn't enter her pussy with her finger, she just rubbed her slit, her finger finding her clit began to slowly move it back and forth. I was now stroking my cock long and hard now and wanted – needed to cum soon or I swore I would die.

"You're being so good Max waiting for me. Are you ready I want to cum with you!" Ann husked

"Yes, Ann cum with me" I gasped as I watched her as she came, her finger quickly rubbing her clit, her breasts swaying with her movements as she pleasured herself. Seeing this was too much for me to take and as I stroked my cock I came, the sticky white fluid splattering upon my stomach and chest. It was the best cum of my life.

Catching our breath Ann told me that was fun and crawled to the middle of the room as she said she would. Meeting her there, we embraced and Ann kissing down my sweaty chest and stomach licked the spent cum from my body.

"That was great," She said to me as we wrapped ourselves around each other and I explored her wonderful body inch by inch with my fingers and tongue. Sucking upon her perfect breasts my cock became alive again and I asked what do we could to do about it without breaking her rules. Smiling, Ann said to trust her and not to move or take any control – let her do it. Telling her I would trust her she told me to lay flat on my back, my cock jutting into the air

Sitting lengthwise upon my cock Ann use the flowing juices from her cunt to lubricate my hard shaft and began rubbing herself back and forth upon it's length. While I knew I wasn't inside of her, the friction of her thighs, the weight of her sexy body and the warm juices flowing from it felt wonderful and so right. Very shortly, Ann screamed she was cumming again and I told her I was too and reached up and grabbed her tits as I blew my second load over both of us.

Ann falling on top of me, we fell asleep and awoke in each other arms. A perfect night of lovemaking.

That was around 36 years ago and as I look at my beautiful Ann sleeping next to me on a hot night in Phoenix, Arizona I'm grateful. Maybe someday I'll tell you the story when I took her and she made me a real man.

The End?

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bybadboy005© 0 comments/ 55664 views/ 2 favorites

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