During my Christmas vacation of senior year I spent some time staying with my older sister. She had an apartment in Atlanta with a roommate, Charlotte. Both of them were flight attendents (stewardesses in those days). There was always a bed available for me as they were gone on flights.
One morning I was watching TV as Charlotte did some dusting. Julie, my sister, was flying. As Char leaned over to dust I got a great view down her cleavage – and she had a lot of cleavage. I was straining my neck for a better angle at that T-shirt when she caught me. I blushed as she laughed and said she didn’t mind. Sitting next to me, Char said she took it as a compliment and asked if I had liked what I saw, what I liked in girls, was I a breast man, did my girlfriend have big boobs. When Char asked if I had ever made love to a girl with breasts as big as hers I said no. Then she said ” You’ve never made love to any girl, have you?” Kissing me on the lips, she whispered “I’ll show you.”
I was scared to death as we moved to her bedroom. She was an experienced woman, 23 or 24 years old, a beautiful blonde with a big chest and I was a dorky old virgin. I was shaking as we undressed and got into bed. As we laid kissing Char had to take my hand and place it on her breast. I was too frozen to make that move on my own.
I loosened up a little as we kissed and explored each other’s bodies. Char was a big woman, maybe 5’9″, shoulder length hair, big breasts with very large dark nipples. Maybe it’s just that they were my first, but in over 20 years since I have never seen nicer breasts or nipples.
Next Charlotte kissed her way down my body and knelt between my legs. After tying her hair back she nuzzled my genitals with her cheek and lips, then lightly kissed the shaft of my penis and my balls. Giving me a wicked smile, Charlotte gently put her lips over the head of my penis.
I know she was being as careful as possible not to trip my virginal trigger but it was too much. I gave some kind of warning and Char released my penis but it was too late. Cum flew almost to the ceiling, I think. My erection wilted as I laided there, embarrassed and splattered with semen. I just wanted to slink out of there but Charlotte was reassuring and kind. Cleaning me up, she said we needed a break to relax.
The apartment complex had an indoor pool so we went for a swim. Alone in the pool, Char told me she had initiated several guys and they had all been nervous and quick. The excitement she could generate in a virgin was a big turn-on for her and she had enjoyed our abortive session upstairs.
Returning to her bedroom I didn’t feel much confidence because my penis was limp in my swim trunks. Char pulled down the trunks and dried me, then knelt in front of me. Holding me full length in her mouth, she gently got me hard again. Then Charlotte stripped off her suit and laid back on the bed. A pillow was under her hips and her legs were spread wide as she parted her vaginal lips for me. I touched my cock to the pink target Char was offering and slid it in. As I pushed into her, Char gave a little groan. I’m not that big so it boosted my ego to make her cry out.
This was in the days before AIDS so I wasn’t wearing a condom. I could feel all that wonderful wet warmth I had imagined for so long. I started to stroke a little back and forth when I guess my nerves returned and my erection disappeared.
First premature ejaculation and now impotence. I was having a bad time of it. Thank God for Charlotte’s understanding and experience. She calmed me down, got me hard in her mouth and we tried again.
This time I laid back and Char got astride me. As she lowered herself onto me Char told me to close my eyes and enjoy the feelings. Then she put a pillow over my face to make sure I didn’t watch. I laid there listening to the sounds of pleasure Char gave and the wet sound of my penis sliding in and out. I felt her big breasts slap against my chest when she bowed low toward me, taking a quick break from her vertical motions. I put my hands on the side of her chest, helping her move up and down on me and feeling her breasts sway against my wrists. Then I felt the stirring in my crotch and grabbed her firmly, forcing my penis as deep as possible as I orgasmed. Charlotte fell on top of me, kissing and congradulating me.
I’ve been marrieds now and my favorite sexual position is still my wife on top with a pillow over my face. She thinks it’s wierd but I’ll never tell her why.
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