By the time I was nearly 27, I had had sex only twice, with two different girls. One was a woman who was seven years older than I and whom I never saw again after that night.
The other was, in a way, a long time coming, a very close friend of mine. The problem was that she had already been married for three years.
Needless to say, I wasn't very proud of myself for either instance once the euphoria wore off, although both experiences in and of themselves were a ton of fun and hot by anyone's standard. To be fair, the main reason I had such limited sexual experience was because I wasn't looking for cheap sex. Sure, I had and still have my share of fantasies that deviate from the norm, but at the end of the day, I wanted a real relationship, maybe even a wife and kids.
The problem was I had terrible luck dating. Terrible luck, that is, until I met Ann. Incidentally, I met Ann the same day I last saw my ex-girlfriend who's a whole different story that isn't worth your time.
It was Ann's first day at work where I was and still am a supervisor. She now works as a manager at a different place, but back then she was starting in an entry-level position. The first time I saw her, I sincerely had no intention of pursuing her romantically, since I had twice tried the coworker route with disaster as the result. Ann was different, though, and immediately caught my attention regardless of my hangups.
Ann was and still is absolutely gorgeous and exactly my type. Her long, straight, very dark brown hair was the first thing I noticed, followed by her deep brown eyes, as soon as I was close enough to see them.
Those features along with her tan skin gave away her Italian heritage. I couldn't believe when I found out she was 30 years old, a few years older than I. I had pegged her at about I remember she wore a blue button-down blouse with a black pant suit and black open-toe high heels.
I even remember the red nail polish on her toenails. She was thin and about 5'6", making her short enough to still be shorter than I when she's in heels but tall enough so that I don't dwarf her when she wasn't in high shoes. Of course, I noticed her firm rack and tight ass as well.
I mean it when I say my intentions were pure, but I am human, after all. We chatted a bit that first day, but I didn't think much of it, other than the fact that I truly was hung up on how pretty she was. However, not only did we work together, but Ann came across as a very strict professional. Don't get me wrong; she was very sweet and friendly.
However, I couldn't imagine she was much fun outside of work, given how serious and task-oriented she was at work. Fate, however, seemed to have Ann's and my paths cross frequently. Part of it too was that she was so pretty that I didn't mind sneaking opportunities to admire her and perhaps get her attention, even when I didn't fully realize I was doing it.
As we had more chances to talk, I quickly found out that there was more to Ann than I initially realized. Not only was she sweet, pretty and, yes, professional, but she was also clever, funny and actually very laid back and a lot of fun to be around. It wasn't long at all before I seriously wondered if she were the exception to both the rules and to my past bad luck that was convincing me to not ask her out. Not three months after we met, I did ask her out and haven't regretted it since.
We had instant chemistry and spent a lot of time together, but neither one of us wanted to rush to get physical. Ann had a checkered past sexually, which I'm still learning more and more about, and with my lack of success in that department, we figured not to complicate things. We did, of course, eventually have sex. It was a slow start, I have to admit, but by the time we were fucking regularly, it got awesome.
I discovered that Ann was a highly sexual being, which made me the one who had to keep up, and I had always had a pretty big libido myself, even if I had trouble finding the right outlet. Ann had me beat in the experience department, which wasn't a hard feat, of course. Within two and a half years of meeting, we got married, and it really was kind of happily ever after. We even had a baby and have talked about having another one. But my point in writing for the first time after years of reading erotica is not to give you my love story.
It is to recount the truly shocking experience I enjoyed with my wife several months back that has led not only to shedding more light on just how sexual a being my lady is, but also other experiences I never dared imagine with my wife before.
I don't even know how that initial conversation turned the way it did. All I remember for sure was Ann's telling me that she "used to" have bi-curious dreams. I wasn't sure I heard her right, so I asked her to say it again. She became a bit defensive, or maybe embarrassed is the right word, and explained that she hung around the LGBTQ crowd a lot before she met me. I knew she had several gay friends, but I didn't know she had ever entertained lesbian thoughts to any extent.
I was more surprised that she would share that bit of information with me, since she had always been very clear on her sexual standards and expected me to live up to high ethics with her. Homosexuality did not fall under those high ethics. I didn't find that type of lifestyle appealing for myself, but the thought of my wife with another woman was as appealing as anything I had imagined up to that point.
I didn't bring up that conversation again but I knew Ann well enough to know it didn't leave her mind. I didn't forget either, and now knowing that there was even the smallest bit of interest there in my wife's sexual appetite had me conjuring up scenarios where we could play it out. While I considered what girl would be perfect for the two of us, fate threw a different curveball entirely.
Just a few weeks later, we were at a family function at a nearby restaurant. Ann had a big family, so we took up a whole room. As you would expect, it was a noisy bunch. Ann and I sat at one end of the room with Brittany, Ann's sibling, and her husband Jack. Brittany was Ann's little sister of about five years. While Brittany isn't as sexy as her sister, she was still very hot.
They looked like sisters, for sure, and had a very similar facial structure. Her colors were lighter, though, by which I mean her hair and eyes were a lighter brown and her skin a lighter tan. She was much shorter, too, maybe not even 5'. I didn't know it yet, but she was just as naughty. While Jack was off with a couple others talking about work and such, Ann and Brittany were having some drinks while I stuck to water and chatted with them. After maybe one drink too many, Brittany asked me what guy I would make out with if I had to.
I told her it was a silly question because, well, it is. Under what situation would my life depend on making out with a dude? Brittany was frustrated with the answer and said that she and Ann would each give a real answer. I could tell that she was very tired and maybe also had too much wine. I would kiss you now, Ann. Now that the thought was there, though, it wasn't going to leave.
We weren't even at the car that night before I asked Ann what her sister had meant by "it's been a while. Apparently, Ann and Brittany had each had lesbian encounters when they were a bit younger and had even "messed around" with each other from time to time.
I later found out they had done a couple threesomes with at least two different lucky bastards who got to fuck both of them in one session.
If only I had met Ann before Brittany had gotten married! I was stunned silent. Like I said, I had always suspected Ann of being guilty of behaviors a little naughtier than simply solo fucks with guys before we met, but I never imagined any of it involved her sister.
Not only was I speechless, but I was entirely turned on. Ann took my silence as disappointment in her, but I quickly corrected her. Ann blushed, laughed and then told me exactly how we could make it happen. It had to be a prank, I thought, but I went along. Brittany came over the next weekend, early in the evening on a Saturday. Their dad was more than happy to babysit our child that night, though he certainly wouldn't have been thrilled to know the real reason.
Of course, it wasn't unusual for Ann's sister to come over, so Brittany casually came into the house wearing her typical hoodie and jogging pants. Her hair was up in a bun, but I could tell it had been straightened and that she had done her makeup, which she normally didn't take the time to do when she was just stopping by. Still, maybe she had just gotten back from a dinner out with Jack or something.
Ann, too, was dressed pretty casually, wearing just sweatpants and a t-shirt. She, as well, had spent some time on her makeup, and her hair was already down. I didn't actually believe what Ann said was going to happen, but I couldn't help but notice those seemingly minor details that hinted that there really was something else planned beside just hanging out. Ann brought out a bottle of wine, and we all sat on the couch. We chatted and drank for about 45 minutes before Brittany finally asked Ann if she wanted to get started on the couch or in the bedroom.
My heart stopped, and my cock got hard instantly. Now my dick was so hard that it felt like it was going to fall off. Next, Brittany pulled off her hoodie to reveal only a black bra underneath. Not surprisingly, I had never seen my sister-in-law in her underwear before, and it was at that point that realize that Ann hadn't been kidding.
Ann responded by taking off her top so that both sisters were in their bras. Shocked beyond anything else I had felt before in my life, I awkwardly asked, "Where do I go?