I'm now thirty-three but the most eventful year of my life was my eighteenth. It was the year of my prom and that was when I lost my cherry to my boyfriend, Eric. Yes it was planned, carefully planned. I'd been on the pill for several months, I'd even talked with my mom about it, that I was going to have sex and she wisely whisked me right to the doctor the very next day.
So, I knew I was going to have sex the night of the prom but Eric didn't; I hadn't told him I was on the pill, I was saving it.
But I did book us a hotel room, my mom knew about it, that I'd be out all night and she knew what I'd be doing. Well, I was eighteen after all.
I did have some dildos and vibrators so there was no worry about any hymen, no, that was gone long before. My mom actually gave me the sex toys, she's that kind of mom.
It was the hotel where the prom was so about twelve-thirty when the prom was being officially shut-down, I suggested to Eric that we go up to a party that I'd been invited to.
We took the elevator up and I slid my key-card in the door and it buzzed open and we went in.
"Where's the party?" he asked.
I was already half out of my dress as I told him, "Right here, Eric, just you and me."
"You mean it, we're gonna do it? Sex? You and me?"
"It takes two, yes, Eric, get your clothes off. I want you to fuck me," I told him.
"I need to go get some condoms, Emily, I don't have any."
"I went on the pill almost two months ago, Eric, come fuck me," I begged as I pulled the covers down and got down, widening my legs open offering him my carefully-shaven pussy for his own.
Now you might think that we're going at this pretty fast and there's little foreplay. That's true except that it was all I'd been thinking of the whole day and night. I was so wet I had to go to the girl's room and fold up some toilet tissue and put it in my panties.
I was ready.
As much as Eric had pushed me to have sex with him, now that my legs were spread open for him to fuck me, he was all of a sudden looking a bit hesitant. But he moved up between my legs and put his dick right up at my slit and began pressing his hips forward while I held still.
I know that it would have been nicer if he'd given me oral sex before he took my cherry but, well, I knew that once I gave him the green-light or the open-legs, he would be singleminded and, honestly, so was I.
He entered me quite easily, I was expecting a lot of pushing and pulling like I'd heard some of my friends describe but once he started pushing it just slowly eased up into me fully, all the way. He just held it there at first letting us feel so full and connected.
It felt nice but it was when he started to move back and forth inside me that the feelings began to take off.
I knew three of my girlfriends were also in hotel rooms in this same complex, all of us with our legs open for our boyfriends, two of us for the first time.
"Oh, Em, this is incredible, just so good. Is it for you?" Eric moaned.
"Really good, not so much right at first but now, oh, yeah. I like doing this. Maybe we should have done it before this, huh?" I asked him pretty much knowing what his answer would be.
"Well, you kept putting me off but it sure was worth waiting for," he said as he groaned and began cumming inside me. Thankfully, he was still feeling pretty hard and he kept going until I did have an orgasm but I wondered for a while if I would.
We did it once in the middle of the night and then once more before we got up to go down for breakfast. Then one more time before we checked out. And, no, I never got my oral sex.
So our first time was really our first four times which began our having sex as a regular thing. We would be going away to college in the fall, each of us to a different school, Eric all the way to the West Coast so while our sex was good we were keeping some distance between us emotionally to lessen the pain when it came time to go our separate ways. I was staying local, attending a small, private university about ten miles away.
The other big thing that happened in my life (things always come in pairs, it seems), was that I got a new family.
My mom had divorced my dad many years ago, I was three when it happened. Typical sordid story, not worth telling here but she dated a little over the years, not a lot, just a few guys each year.
But the last couple of years, she'd met a man who was a vice-president at the bank where she did business. One thing led to another, he found out she was single when she filled out a refinancing application and, after the deal was struck, asked her out to dinner.
They'd pretty much been together since and he'd stay the night a number of times so it had gone that far for sure.
So I wasn't surprised when she told me that he had asked her to marry him and that she was probably going to.
He had the larger house and the plan was for us to move and they would rent out our house as income property.
So, about a month before the wedding, we moved into his house which was somewhat larger and, yes, nicer, than ours. I especially loved the in-ground pool in the back, that made it easy for me to work on my tan.
About three months before they got engaged, that's when I found out that he didn't just come alone, he had a son, a son who lived with him. Oddly, Tim was the same age as me.
It was then that I knew I would no longer be an only child, I'd be sharing my mom's attention with a stepbrother.
I still remember the first day I met my soon-to-be stepbrother. My mom and Robert, her new fiancee, had planned an outing for their two children to meet and when they came over to take us out for the day, I got to meet Tim.
Well. He was hot. Really hot. Just over six feet tall, a nice tan, it seemed that he used their pool all summer, and he had a killer smile.
You can ask me why I felt flirty that first time and I'm not sure I could tell you. But I was and so was he. Looking back on it, two new step-siblings meeting for the first time, well, it seems odd that we acted more like we'd each just met some new person at school who seemed sexy rather than someone I was going to be somewhat tied-to as a family member.
But we did smile our sexy smiles and make a few passing remarks that had a bit of a sexy edge to them.
That first time when we met was nice but we really didn't start keeping in touch with each other and the next few times we were together there was more friendly talk mixed in with a bit of flirting as well. It was fun but not especially serious.
I was still involved (read: fucking) with Eric and so I wasn't especially trolling for any new cock.
I know that sounds really slutty but, well, I'm afraid lots of us girls think that way today. Sex is not far from our minds no matter what we're doing.
So, Mom and I planned the rather simple wedding that they wanted, mostly a few friends and family, and we moved in with Robert and Tim a few weeks before the big day.
I immediately fell in love. With the pool. Oh, it was beautiful, large and partly shaded by a large overhead canopy. It also extended into the house, into a workout room complete with exercise equipment, a sauna and a hot tub. It was incredible.
There was a small pool in the exercise room which led out to the outdoor pool and it was enclosed by a large glass window which dipped into the pool sealing the house from the outside. The minute I saw it I wanted to swim from the small indoor pool, under the glass to the outside. That was the height of luxury as far as I was concerned.
So, we moved in and a few weeks later the wedding took place and Mom and my new dad went on their honeymoon for a week to Cabo San Lucas.
Now, before you panic thinking they left both their kids alone, we were each eighteen and had driver's licenses and Tim's aunt and uncle were only about two miles away and the freezer was stocked.
As soon as we'd moved in, I was at or in the pool much of the time. I had bought some new bikinis, including one thong set that I didn't show my mom, yes, it was hardly there, I figured I'd use it when she was at work.
Of course, now Tim and I were together much of the time and we continued our mild flirting, it was fun, after all, and even did a little kissing and fanny-slapping at times in mostly an innocent, fun way.
But I was also teasing his eyes, letting him get some glimpses of his new stepsister, especially around the pool on my new thong outfit. I was shaved clean these days, just about the only way you could wear this suit. It covered my nipples and my slit and that's about all.
I knew Tim was watching me from his bedroom window as I sunned poolside and I imagined him jacking-off up there as he looked down on his mostly-naked new stepsister.
There was one particular afternoon, it was the Monday before the wedding, that I rolled over, looking up, and saw that he was in his window, hidden back, but I still knew he was there. I was feeling really horny and, even though I didn't have on the thong outfit, just a normal yellow bikini, I reached around and loosened it, slipping it up off my boobs to give them some sun. I slathered them with lotion, knowing I was giving him a good show.
So, yes, I was teasing the poor guy, especially whenever I was feeling particularly horny and naughty. That was a lot because Eric and I were not getting along like we had been, he was acting like a jerk quite a bit now and I wondered if it was because I was now living in the same house with another male my age.
.... There is more of this story ...