(This story was inspired by "Impossible Situation", one of my favorite stories from the Old Impregnorium. I was never able to contact the original author JJenny, but I hope this will be taken as my homage to a piece that certainly fired my imagination.)
Before I tell you my story, I should probably tell you something about myself. My name is Maeve, which was my grandmother's name; since I was an only child and my mother couldn't have any more children, she thought it was appropriate. Apparently it means "intoxicating", but maybe "easily intoxicated" would be more appropriate in my case...
Unless you like short, dowdy ladies I'm probably not fantasy material, although I've always been proud of my double-D's and try to work out. Stuff tends to sag as you get older, though, and the summer this happened I was feeling my age with my 50th birthday just around the corner. The girls at the office tried to cheer me up, telling me I was cute with my blonde bangs, but I definitely felt my age as I noticed my monthly friends were drying up and my doctor confirmed that I'd soon be entering my change of life. But anyway, it had been years since I'd been with a guy so I was resigned to being single and childless.
I still enjoy a good party, though, so I was game when our office manager June invited me to join a road-trip to Monterey for Independence Day. I was a little reluctant at first since we'd be going to a beach party, and I wondered if I might look very dumpy compared to the younger girls from the office. June actually felt the same way, though, since she was in her early forties and had never gotten her figure back after having two kids in her twenties. To boost our confidence, she offered to go bathing-suit shopping with me and talked me into a rather-revealing orange bikini that definitely showed off my boobs. When it was actually time to go, though, I pulled on a long white T-shirt over the bikini, along with a floppy sun hat, sunglasses, chunky clogs and a beach bag.
Well, it was fun; the drive took over 3 hours but it was a sunny day and the beach was packed when we got there, full of people enjoying live music and the natural beauty of the sea. I kept my T-shirt on for most of the morning, though, until after I started drinking and got a good buzz going. Then I took my shirt off to expose my bikini and enjoyed occasional glances from guys who appreciated my cleavage; there were plenty of younger girls around, though, so I didn't entertain any illusions about hooking up with anyone. Only June's young son looked at me with sustained interest, though not exactly for the reason I thought at first. Although I didn't know the boy well, June said that her son Larry was very bookish and shy so I wickedly decided to give him a treat with a flirty wink and jiggle of my boobs. Sure enough, Larry looked flustered and uncomfortable and avoided my gaze when I looked right at him. But then the 15-year old summoned the courage to come closer and note that I was turning bright red with a bad sunburn.
"Oh, shit," I said; "you're right..."
That was typical of me; I started drinking and spaced-out on what I was doing. I had started rubbing some lotion on my legs earlier, but didn't bother with my upper body while I still had the T-shirt on.
"I just wanted to let you know..." Larry said, as he started to move away.
"Hey," I said, "would you help me rub some lotion on my back? I'd really appreciate it."
Although Larry was obviously uncomfortable around girls, he overcame his shyness enough to come back and help me, rubbing lotion into my back and neck and shoulders, but nervously avoiding the front of my body. I had to take care of that myself.
"Thank you," I said, taking the tube of lotion and rubbing some into my boobs. "You're a gentleman."
"Um ... thanks..." Larry said, obviously enjoying my cleavage before anxiety pulled him away. "Bye."
Then things got a lot more blurry, as I've never been good at holding my liquor and continued drinking a lot. I do remember the sun going down and someone starting a bonfire, but not much else. Although I'd come with June, I vaguely remember her being very angry about something and driving off before I was ready to go. But other girls from the office had also come on the trip, so some of them offered me a ride home in the back of their SUV. All the front seats must have been packed, since they tucked me in the back among some blankets and coolers, but I hardly noticed since I was completely wasted. All I remember is it was cozy and dark and I was soon out like a light...
For me, the beach party had been very frustrating. At first I thought it would be cool to join my mom for the 4th of July trip, vaguely fantasizing about meeting some cute girl there, but of course I was just as shy at the beach as I was at home. The only girl I really talked to was some old chick from my mom's office who was so drunk she didn't even realize she was roasting in the sun. Glancing at her boobs did put a charge in my cock, but she was like 50 or something way too old for me. I was brave enough to help her rub some lotion on her back, but I soon felt the familiar anxiety of being close to a girl and had to run away. Feeling pathetic, I then snuck a beer from an unguarded cooler, but that just left me feeling even more frustrated.
When I tried to talk to a young girl later, she just ignored me; so I returned to sneaking beer until Mom caught me. Naturally, she was livid.
"Young man, you are so grounded! Come on, we're going..."
But for once I actually stood up to her. I guess it was the beer talking.
"You can't tell me what to do, bitch!"
"How dare you!" Mom said. "I will leave you here, young man!"
"Fine! I'll find my own way home!"
So I felt empowered for about 10 seconds, until Mom stormed off and I remembered our home was in the Central Valley more than 200 miles away! Not for the first time in my life, I thought about humbly apologizing to Mom, but Mom really wanted to teach me a lesson and took off without me. Luckily, though, some other girls from her office had another SUV handy and took pity on me. Ordinarily, being around so many girls would have given me hives, but I mostly just wanted to get home somehow before it got really late. I'd worry about apologizing to Mom later.
The only problem was the front seats were all occupied; all the driver could offer was the rear cargo compartment.
"There is someone back here already," the driver said, "some chick from your Mom's department, I think. But you're pretty small; just wedge yourself in there if you can."
"O ... kay..." I said, trying to move some coolers and blankets enough to wedge myself in. Then, as the driver closed the hatch on us, I noticed the sleeping lady was that same older lady I'd helped with the suntan lotion earlier. Instant nervousness again; but she didn't seem to budge at all as I tried to make some room for myself. Smelling of booze, she was probably out cold. My nervousness subsided a little.
More compelling at first, as the SUV got underway, were the nearby coolers. Remarkably, one of them still had a few beers in it so I happily helped myself. Up front, the girls were chatting loudly and listening to the radio, so I could open the cans without being caught. Maybe it was wrong, but my buzz from earlier was wearing off and I was still worried about what would happen when I got home. I figured a few beers might help me get some sleep at least.
For a guy who doesn't drink often, the light-headed rush felt wonderful and I briefly wondered if any of the girls up front might be drunk or desperate enough to try anything. Even with a buzz, though, I wasn't bold enough for that. I knew I was a nerdy dork, and might as well accept that; my best friend Joey and I were classic virgins, and would probably be that way well into college.
So I tried to stretch out a bit, and only then recalled my companion in the compartment. I didn't know her name and she was facing away from me toward the rear row of seats, but a flash of passing headlights gave me a good look at her backside; with that blonde hair and orange bikini bottom, she was definitely the same lady. I kind of wished she hadn't pulled a T-shirt on over her top; I'd enjoyed looking at her boobs. But maybe, if she really WAS passed out, she wouldn't mind if I slid her shirt up a little...
"Um, lady... ?" I whispered, giving her shoulder a nudge. "You awake?"
She didn't respond, but it was starting to get quiet up front as the driver turned down the radio and the passengers were trying to get some sleep.
"Lady... ?" I continued, giving her shoulder a stronger nudge. But she was definitely out of it; I leaned in closer to get a look at her face and saw she was definitely passed out, not only smelling strongly of booze but also drooling a little spittle from a corner of her mouth.
Then an idea started to percolate in my mind; maybe I could do more than just lift her shirt a little. Nobody up front could really see in the back very well, and I myself could only catch an occasional glimpse of my surroundings when another vehicle passed by. And here was a flesh-and-blood lady passed-out drunk, sure but still right in front of me. The anxiety was still there for me, but it wasn't nearly as strong with a lady who didn't even know I was there...
.... There is more of this story ...