Woulda….. Coulda….. Shoulda…. Didn’t!
Introduction:
Many of you have read about young Bill and Granny. If you didn’t notice, except for Granny, I wasn’t really an aggressor. I planted a thought and let it grow until they made it obvious they wanted me or, they took me.
First was Janice’s older sister. By dating Janice, I was the envy of all the guys my age. The word around town was that both older sisters put out at any time for any cock. So, I was or would soon get all I wanted.
Two to three years later I got her cherry. But, this was at a different time.
I went to her house and she was gone. Her older sister answered the door wrapped in a bath towel, NOT a bath sheet like we have today.
She invited me in to wait explaining that she was using a sunlamp. I sat, she asked me to move to another chair and went in the next room. In the next minute the door creaked open clearly exposing her naked body to be viewed only from where I was sitting.
I sat looking and chatting for about an hour but, never moved. At the sound of Janice opening the front door the viewing door swung shut.
Several weeks later she came in to find Janice and I necking and said, “It’s okay Jan you are too safe with him”.
Then one summer on a Saturday after noon. I was at a local soda shop and met a girl from the next town. We took a back booth and necked. After a very short time she was “asleep” on my shoulder with I my hand in her bra, and a finger in her pussy.
She woke up and suggested we go for a walk. The park was crowded so we strolled to a hidden maintenance area at the local campus. For an hour or two we played. And, caused each other to cum several times.
Later in life, I would have pinned her to the wall and fucked her! But then, I only knew “missionary”, and she did not take the lead so that was it. I never got her name, only her panties.
My next shoulda was the summer after high school. I was in a expo at the state fair and met an older lady (26 or 27) that I spent some time with. After the final show, we left the fair grounds and strolled around the area necking for some time.
She invited me to take her home and I accepted. After two long bus rides and a short walk we got her apartment. As soon as we closed the door she took me in her arms rubbed her crotch on my stiffie and French kissed me! I grabbed her tits and asked, “Are we going to fuck?”
She responded, “Sssh don’t wake my room mate!”
I whispered, “I’m sorry”. And left!
Later on that summer I was laying under the stars in the backyard of a teen that also been a part of the expo. It was two days before I was to leave for college and I was playing with a great set of tits. Those tits had alerted her clit to wake up and be eaten.
She moaned, “Why is it every time I’m ready and want to screw, the guy goes out of town”
I responded, “I’m so sorry”, licked her to another cum, and dumped a load in her mouth. And left!
Then came the worst “didn’t” of my life. I had enlisted and was using my last day home to look up friends. I was in a soda fountain and ain walked a high school friend. She was a year ahead of and the biggest rack on a trim body I ever met. (Think Dolly Parton).
We sat and talked thru a soda: she was married; he was in Korea; I was invited to her apartment; I went!
We talked til 4AM the topic was always about sex: her first time; (What is the fuss? — it did nothing for her!) her second time; (She came) what she liked; (everything) how many boy friends she had; (7-9) how cold it is in Korea; (look at the fur lined jock strap she made) she “got” comfortable; (many times) I rubbed her smooth thighs; (short loose shorts) yes, her husband would like that thin tight sweater; (Her nipples were lovely) Would I try the jock strap on; (It a was sooo warm) she loves oral; (So do I) she never touched me; (What do I do) it is four o’clock I must go; (Do you like my baby doll nighty?) half way down the steps, with her above me, here’s a kiss; and damn it, it was a hot French kiss!
I was knocking at her door on my first leave. And got a big, “I don’t do that any more”.
Thirty seven years later she still didn’t!
Now I was in the service and in spite of servicemen’s reputation there were a few coulda events. (Very few)
I was a waiter a couple nights a week as the Staff Club. And had developed a set of regulars including a sexy redhead. One time as she and her friends were leaving at last call she asked me to sneak her drink out for her.
I took the chance and met her in the parking lot. As I handed it toward her she pulled my head down, kissed me, handed me a slip of paper, and said, “Bring it to this address in base housing”.
I already had the experience of being in a bed when hubby came in the front door to announce, “Baby I’m home!”
She had to go to bed without her drink or me!
Then there was that time at the base pool a bikini “uncovered” 16 YO tried to take me home for lunch. —— I went to the mess hall. (Shuda tried to stir up a mess hole)
I remember taking Sandy home and going up the outside stairs to her bedroom. She pulled me over beside the bed for our first kiss. I went back down the stairs caus my bud was waiting in the dark car.
Took divorced carhop home, got introduced to her live-in ex and left.
Walked out on a Woman Marine, what Marine could eat another Marine!
First time in Iwakuni, Japan walking across Skivy Bridge with Master Sgt; local “lady” opened her kamona baring it all; she said, “I give you something you never had before Sargent”.
He slammed my back with, “Run like hell Smith, she’s got leprosy! I RAN!!!
An older sister repeat. A girl I was fucking’s sister was getting married, I was at their house the morning of the wedding for a big two family breakfast. I ate at the base, the bride didn’t feel like eating, we were on a day bed on the sun porch. She started to tussle with me and I ended up laying between her legs. her panties gone, sundress around her waist, and my cock in her hand. She whispered, “Fuck me hard”.
I struggled, yelled, “NO I CAN’T!”
Both families ran in; I jumped up; hubby “to be” shouted, “Why wouldn’t you fuck my sweet bride? Since you think you’re to good for her, get the fuck out!!!”
I went back to the base.
I was a Marine dating, hell, fingering a local college gal that was afraid to fuck. I fucked her mom.
