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.
I continued to play with my new stepbrother, giving him little peeks, little brushes against him, quick little kisses, even a few darting the tip of my tongue between his lips. Oh, I know, but it was fun and made my pussy tingle.
Then, three days after the wedding, Eric and I were out and had a big argument and I told him to take me home which he did. I stormed out of his car, ran to the front door, unlocked it, and ran up to my room crying.
As far as I was concerned, we were through.
So, I sat there cross-legged, rubbing up under me, frustrated in so many ways.
Then, I thought, fuck it, and got up, took my clothes off and slipped on a clingy, black negligee that I'd bought for that first time with Eric. I left the panties in the box, turning in my full-length mirror getting a good view of what my new stepbrother was going to see.
Then, I slipped a robe on and went down the hall to his room. The door was open and he was stretched out watching something on television.
"Whatcha' watching, Tim?" I asked.
"Well, here's something better to watch," and I stepped in front of the television and opened the robe, dropping it off my shoulders onto the floor.
"Omigod, Emily, you are so beautiful, I..."
"Here's the rest," I said lifting the hem over my head and dropping the nighty on the floor.
"Oh, wow, I can't believe this. I know you have a boyfriend and all so I never ... you are so pretty."
"I'm ready for bed, Tim, tonight, right now, are you ready? Like together?"
"You really mean it? What about your boyfriend?"
"He's history. So, are you ready?" I asked as I got in bed with him and pushed him over kissing him, shoving my tongue into his mouth while I gripped the bulge in his shorts.
I held him down kissing him for a minute then got up and began loosening his belt and opening his shorts. Then with one big tug, I pulled them straight down and off followed by his white briefs.
Up jumped a beautiful, light pink, thick, long penis. Oh it really was beautiful, I thought as I took it in my hand while he was pulling off his polo shirt. He laid back down and I could see just how beautiful my stepbrother was with his all-over tan. I bent down and kissed it right on the soft, round tip then let my lips slide over the crown to give a few pulls of pleasure.
Then I got up over him, squatting down, reaching under to hold him steady as I rubbed his hard dick across my wetness then began pushing him up inside me. As I felt him slowly penetrate me, I knew this would only be the beginning of his cock being deep inside me. We were home together alone with each other after school and it was soon summer and this is what I planned for my summer vacation: fucking my stepbrother all summer long. It felt that good.
His hands were rubbing and playing with my boobs, his fingertips running circles around my sensitive, excited nipples as I began rising and falling on his long, thick cock.
Delicious was the only word I could think of as I scissored up and down over him, looking down at him below me. My pussy felt filled and fulfilled. It was full of a male cock and that was exactly what my pussy was meant to hold.
"Oh, Em, I think ... uh, UH, UH, uh, oh, wow," he groaned as I felt a new warm slipperiness inside as I drew up and back over him. As I rose and fell on his hardness, I began pushing down to take him as deeply as I could. It was feeling so good all the way up my vagina from the outer lips deep to my cervix just tingling and throbbing as I moved his cock in and out.
"Mmm, god, this is so good. My own stepbrother. Right in the next bedroom. Oh, we're gonna be doing this a whole lot. I sure hope you're as horny as I am. And that's a lot," I said giddily.
"Don't worry about me, Emily, I'd never pass a chance to have you in my bed. And we've got the rest of the week before our parents get home. We can sleep together."
"And we can work on getting some over-all tans out by the pool. You look like you're tan all over already."
"I was using the pool naked before you and your mom moved in but Dad said that had to end. But, when they're not here, well, that'll be fun, just you and me, naked swimming and getting some sun and, well, doing this, right?"
"Yes, especially doing this. This is the best. And I'd love to do this out by the pool, that's so sexy."
I squatted on him sliding up and down, yes, it was delicious. He was so handsome under me, so obviously thrilled that we were together like this as was I.
The feelings were mounting, this was better than my sex with Eric who seemed to mostly do it to get himself off, with Tim, he was more wanting it to be good for me.
"Mmm, oh, yeah, omigod, I'M ... UUH, UUH, OH, OH, oh," I screamed as my body was swept up in the most luscious orgasm I'd ever had. I fell down over him as we kissed and kissed, his cock still inside, my hips still rising and falling, keeping the newfound heat blazing where we were joined as one.
"Don't stop, Emily, it still feels so good," my new stepbrother whispered in my ear following his words with his wet, sexy tongue.
I fucked him to a second climax for us both and we went to sleep in each other's arms.
The sun streaming in around the corners of his window drapes the next morning woke us to a new life together as he rolled me onto my back and pushed up into me welcoming the new day together united as one.
What a way to wake up, I thought as I looked at his happy face smiling down at me. I lifted my legs onto his shoulders so he could push deeper which felt so good.
Oh, sex first thing in the morning, how lovely. I was really liking having a stepbrother in the same house, even right in the next room. And I was loving sleeping all night together and waking up together, that was the best.
He was fucking me slowly, something that Eric had never done, he always went like he was in a marathon. This was lovely, so nice. I was getting to know just how good sex could be. And how good it was having a horny, healthy guy in the next bedroom.