This story is PURE FICTION any resemblance to real life events are coincidental.
1987
The story begins when I'm 19 year old high school senior living in a apartment with my divorcing dad. Dad was never there and I mean never. His girlfriend lived like 4 miles away and I didn't give two fucks.
Prom night my buddy Tim and I double date to the dance. His girl Sherry and my girl Anna got along well enough that the night went pretty smoothly except both Tim and Anna had work commitments in the morning. So about midnight Tim takes off for home which is 15 miles south of town and I take the girls home. First Anna because she needs to be up in the morning. So we hop in my car and drop her off with a quick peck to the cheek. Sherry jumps out of the back seat and sits next to me on the way to her house.
Now let me tell you about Sherry, these details will be Important later. She stood about 5'3" 135 lbs pure blonde with double d breasts and a cute birthmark between her left thigh and her butt cheek.
Back to prom night, After Anna went into her house, Sherry and I started back to her house and on the way she tells me she didn't want to go home. So I asked her where she wanted to go and she said back to my place. So as we are cruising back to my place Sherry asks me the question. Gentlemen you know what it is the am I cute / sexy question. Well I tell her flat out I think she is sexy in her dress so she leans in and gives me a kiss at a stop light. Well obviously the kiss has stirred something in her loins because the next thing I know is her hand is rubbing my cock as I'm headed back to my place.
Let me explain some logistics to everyone. Anna lived across the river and about 15 miles north east from my place and all of it city streets so Sherry and I had time to fool around and did we.
So I'm about 6 blocks from my place and hard as a rock kissing Sherry at every stop sign. Well at one of these stop signs she unbuttoned my pants and fished out my cock and under the dashboard lights engulfed it. So I had to pull into the old Kmart parking lot and park for a minute while she worked my wood like she was possessed. Now Sherry was a decent blowjob artist but not in Anna's league. Anna could take all of my 8+ inches down her throat and not miss a beat while in a torrid 69.
Sherry and I hadn't been there a few minutes before a car pulls up behind us and it's the cops wondering what we are doing. Luckily I had quit drinking 3 hours or so before and brushed my teeth etc. before I brought the ladies home. So I roll down the window and it's my almost retired cop friend Carmine. He asks me the standard battery of questions and for Sherry's id ( she was 18 thank Jesus) and told me to go home. Yes sir we left with my cock still hanging out of my rented prom tuxedo.
Once we walk into the apartment Sherry grabbed me and we headed to my bedroom shedding clothes the whole way. Now you all know what happened next, yep we fucked till the sun started to come up, got a few hours of sleep and fucked some more.
I knew Sherry was on the pill just from information from my buddy Tim, so I didn't bother wearing condoms at all. She took my 8+ like a champion and I even got her to squirt a few times especially after I violated her chocolate starfish with my thumb as we were doing it doggie style.
So that started our torrid secret relationship. Almost every Friday night my buddy Tim would go to the races at the fairgrounds and then work the next morning. Sherry would come over and we would fuck for hours and she would either spend the night or go home. Your wondering about Anna, she dumped me the week after prom, which was cool for me because one of her girlfriends thought I was just swell and came over weekly to "console my broken heart".
Skip to August and I fuck up bad and get caught making a 5 finger discount while drunk and get caught. Monday I get hauled before the judge and given a choice Military or prison. Well given the choices it was to the military I go. So the next day I sign up for the Navy, shipping out in October.
Now after I tell Sherry the situation she tells me no more fucking around behind Tim's back because he proposed to her. Well I was cool with it because I had to get shit right before early October.
Now I didn't see either one much till about a week before I went into the service and Tim springs the idea of getting married before I leave for basic. I ask him why and he tells me Sherry is pregnant. I'm like oh fuck in my mind but I tell Tim I think it's a fine idea. So the Friday before I ship out we run down to the courthouse and I witness them getting married. Honeymoon suite is a motel 6 that night.
Saturday morning comes around and they go tell the parents. A nuclear explosion would have been a better disaster. Sherry's single mom lost it and disowned her and threw everything of hers out of the house. Tim's mom and dad were ecstatic to kick Tim the fuck out of the house also. Your old enough to get married then your old enough to live on your own, good bye. This started a sequence of events that will make you go WTF.
Intervening years