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It was the first day of my third year at MIT. My major was civil engineering but I had signed up for this statistical analysis class. As I walked into class for the very first time, I almost bumped into her; there she was with all her goofy looks. It was Gertrude from middle school and high school. Being polite, I said, ‘Hi Gertrude.”
She just gave me an ugly look and stumbled on by. She just stumbled on by me without a word. Stumbling was the best way to describe the way she walked. It was as if she was falling forward and her feet were trying to catch up. She had frumpy looks and matted hair. Her little tits were too low on her chest for such small ones. Gertrude never smiled.
All the boys in school had picked on Gertrude with no letup. All the boys and even some of the girls had played Gertrude germs all day long. If you brushed up against her in the hall or came in contact with anything she touched, you wiped your hand on the next person and said, “Gertrude germs.” Then that person wiped their “Gertrude germs” on somebody else. We always made fun of her, like asking her if she was walking with a stick up her ass or what happened to her tits. I was one of the worst little bastards.
Somehow she had survived our torment and here she was at MIT. MIT had a very low acceptance rate so she must have had something on the ball.
My nursing student girlfriend had broken up with me over summer so it had been over a month without pussy. And MIT was not a place to find any. Back then girls were very, very scarce at MIT so what to do? Gertrude? NO! Not Gertrude. I wondered if Gertrude had a pussy, but who cares. It is probably goofy if she does.
As fate would have it Gertrude sat to my right front in statistical analysis. The professor was very boring. All he did was read from his book, word for word. The book was brilliant but I had bought it and read it as soon as I had signed up for his class. So her legs, sticking out of her dress were the only thing that could hold my interest. OMG! I am looking at Gertrude legs. But is there a pussy where they come together? When she sat somewhere else, I was disappointed.
Over the next several days, my attempts to talk to her were met with the same cold shoulder. Then one day, outside class, I said, “I know a lifetime of apologies will never make up for years of being such an asshole, but please, can we start over.”
She gave me a dirty look and said, “Careful, you might get Gertrude germs.”
“Let me take you to dinner.”
“Ha! Do you have any idea how many boys asked me out in high school? Meet them at such and such. But they never showed up.”
“Okay, I will pick you up.”
“I want to take you to dinner.”
“Look, I will give you cab fare when I pick you up. If you think I am being an asshole, just leave.”
“But what’s the point? We shrinking izle have not seen each other for over two years. I am still the same ugly duckling and you are still one of the cool ones.”
“Gertrude, what I did all through school was not all that cool and you are not ugly. You were different so they (we) picked on you.
Then she just walked away. I continued to ask her out every day and she continued to turn me down. It was becoming an obsession on my part. But then one day it happened; she smiled when she said “No.” I had known her for over eight years and never seen her smile.
She said, “If I go to dinner with you, will you leave me alone?”
“No. Not unless you really want me to.”
We went to dinner that night and had a good time. Was I actually out with Gertrude and enjoying it and having a good time? Yes! She was intelligent company and I wanted to fuck her. But I knew if I tried to rush her, it would scare her off? Her dress came to just above her knees and her legs were beautiful. I really wanted to see where they came together. Maybe I could have a little taste? Or maybe I could have a big taste? Her legs made up for all her goofy things.
Later that night, when I drove her home, I walked her to the door of her rooming house. She got a little ahead of me and I had a view of her legs again. My manhood started throbbing and a tent appeared on the front of my pants. I wondered what would happen if she saw it. When we got to her door I took her in my arms and kissed her. My cock was rubbing against her front. My tongue explored her mouth and got tangled with hers.
Then she confessed that it was her first kiss and asked, “Did you ever, you know?”
“Yes, a long time ago.” That was not really a lie. A couple months can be a long time ago.
She looked real serious and said, “I am sorry but I am scared.”
“Scared of what?”
“I know you only took me out to have sex, but I am scared. I have never done it. I am sorry if that disappointed you.”
“How can I be disappointed after a nice meal with nice company?”
“I may be a naïve little virgin but I know what that thing is that you are pressing against my belly. And I am no trophy date.”
“I admit that you have me plenty excited and I want to make love with you but don’t do anything that you are not comfortable with.”
We kissed for a few more minutes and said goodbye.
A couple nights later we went to diner again. This time she loosened up more. I wondered what my old high school classmates would say if they saw me out with Gertrude and enjoying it. After dinner, we caught a movie and sat way up back. I folded up the armrest between us, put my hand up her skirt and started massaging her inner thigh. She touched my love stick and then jumped away as though it had bitten her. When she came close again I went back up her skirt and continued sihirli annem izle where I left off on her inner thigh. After a long time my hand found her pussy mound and started rubbing it. She started moaning softly and put her hand on my cock. I moved her panties aside and stuck my finger in her pussy. I loved the feel of her vagina and she was getting wet. She was moaning against it and opening my pants. When she got my cock out her little hand started going up and down on it. But that was as far as we went that night.
When I picked her up for our next date, she seemed to have a lot on her mind. When I asked what was wrong, she burst out crying. She finally said, “I got used to being the little nerd girl that nobody wanted but you made me special and now I have to lose you.”
“What on earth are you talking about?”
“You want to have sex. If I don’t give it to you, that will be the end. You will dump me. But if I do, you will have gotten what you were after and not have any reason to stick around.” By then she was crying loud and shaking.
I held her in my arms for a long time. We never made it to eat or anywhere else but just sat in the car. Finally she said, “If my only choice is to lose you because I did or lose you because I didn’t, I would rather have something to remember you by. Let’s do it.”
“Are you sure that is what you want, Gertrude? If that is what you want. Once your hymen is broken, there is no putting it back together.”
“Let’s get a room. It will be my treat. I want my first and maybe only time to be special.”
“I will pay for the room, but are you sure that you are ready?” Somehow, I had gone from making fun of her to craving and respecting this little lady.
When we got in the room, we started kissing and fondling each other. For a girl with no experience, she became a great kisser in a short time. Her mouth tasted good as my tongue entered it. Then we took our clothes off and started kissing each other’s bodies. Her tits were small and sensitive. The more I kissed and sucked her nipples, the more she moaned and softly screamed. Then I got between her legs and started licking her pussy lips. She jumped at first and then started pulling my head into her crotch. I nibbled her clit with my lips and she screamed loud. I cautioned, “Careful, we will attract company.” My head was still between her legs so the licking continued.
She said, “Am I supposed to do that for you?”
“You may try it if you are comfortable with it.”
“Will it make you happy?”
She started sucking and stroking. It felt wonderful. Then I turned her around and got her straddling me. I started rubbing my bulb up and down her slot. Her little pussy felt fantastic, rubbing the head of my love stick. She was very wet and I had passed the point of no return. With her pussy juice and sizi dinliyorum izle my pre cum, we were well lubricated so I said, “Last chance to back out.” That is when she slammed down on me, breaking her cherry and nearly breaking my lap. As she started stroking me, I could feel the back of her pussy rubbing the head of my cock.
If they gave an award for pussy rookie of the year, she would have to get it. At first I blamed it on the fact that I had not been fucked since mid-summer but I soon realized that she was that good. She kept stroking back and forth and up and down and then with my cock buried all the way in, she started going round and round. The feeling was better than anything I had ever experienced.
I wondered, where did a little virgin girl learn to fuck like that? So I asked, “Where did you learn all this?”
Even though she was bouncing on my meat and her pussy felt like a million magic fingers, she paused and spoke very sincerely, “This is embarrassing but sometimes I watch a little porn. Now that we are doing the real thing, I just go with whatever feels the best. Do you like it?”
“I love it”
Her cowgirl was fantastic, but then she turned around and rode me reverse cowgirl, which felt just as good. When I couldn’t hold back any longer, she said, “Do me doggie style. I think it would feel good if you came in me from behind, don’t worry about getting me pregnant, the doctor said that I can’t conceive.”
As I pumped my swollen, throbbing, hungry, manhood into her from the rear, I thought that I never wanted this to end. It felt that good. I tried to slow down but it felt too good. I grabbed her hips and rammed my cock as deep inside her as it would go. Then I started pumping faster and faster. It felt like the top of my head was being sucked in and blown out the end of my shaft. My balls delivered a huge load and the feeling kept surging over me. Wave after wave of ecstasy rolled over me as river after river of semen shot into her willing hole.
We laid on our sides for a while with my dick still in her. My love stick was just as hard as before I came, so she said that she wanted to try missionary style.
When I climbed above her and entered her thrilling little passage, we started kissing again. Her kisses continued to be amazing. Then she said, “I love kissing you.”
“I do too.” As my manhood continued to stroke inside her, her little pussy never got loose. In fact, it never stopped feeling wonderful. As my hips went up and down and my penis slid in and out of her tight little passage, she started to shake and have her first orgasm. A few more strokes and then I was coming too.
She tried avoiding me the next day in class. I asked, “What is wrong?”
“Well, now that we did that.”
“Gertrude, now that we did what? I want to see you tonight.
“What if you get Gertrude germs?”
“Honey, if I spend the next 50 years saying that I’m sorry, it won’t make it right. But let me try.”
We were married during Christmas break. All that happened over 30 years ago. We have 2 adopted children and 5 grandchildren. We still make love almost every night. Sometimes we do it more than once.
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