Early last year my boyfriend of ten years and I broke up briefly. During that time, I dated a guy for two months which really upset him so when we got back together I told him I'd do anything to make it up to him. I was very apologetic as it was a silly thing to do and he agreed that I would have to do some things to make it right. We always had a very adventurous sex life, we were open to experiences with other people as long as we were honest about it and he liked seeing me take on sexual challenges and sometimes be in compromising or somewhat humiliating situations to see how I'd handle them. He also liked knowing that I was a bit of a slut at heart which is why he came up with a list of sexual challenges that I had to complete before I was allowed back at the house. Each challenge had to be documented with photo or video evidence to prove I did it and I had one week to complete them all. The list he provided was as follows:
contact and have sex with one of my former high school teachers
make a taxi driver accept "favours" as payment instead of money
have a doctor make an overt sexual pass during a routine examination
perform on amateur night at a strip club
perform the "pizza delivery challenge" (this is when you order a pizza and at the very least show your naked body to the delivery guy...sometimes more)
Initially my impression of this list was that some were absolutely impossible but he was uncompromising and I desperately wanted him back so what else could I do but accept.
My impression of each item on the list was as follows: No. 1. - Finding a former high school teacher to have sex with would be VERY difficult. I am thirty and am not of the generation that has their teachers on social media. I can barely remember most of them and would really have no idea how to find any I might have found attractive, let alone proceed with something that wild...or even if they would remember me as I was much different in high school than I am now. This one was a biggie.
No. 2. - A cab driver didn't seem that hard. This one was doable. I regularly use cabs and am regularly hit on by cabbies. I also have a somewhat regular cab driver that has picked me up from clubs and from various sexual experiences and although we've never had an obvious discussion about it, there have been certain things alluded to on the way home. This one I thought was possible.
No. 3. - No way was this one happening. I cannot imagine a doctor in his right mind that would compromise their livelihood no matter how hot the girl or how exciting the thrill. This one was clearly the biggest challenge. It occurred to me that maybe there was a way around it...to be elaborated on further at a later time.
No. 4. - Though this one is actually quite doable as there is a strip club in my city that offers amateur night, I do have an actual real life and a professional reputation to protect. No way was I being this obvious about it in my own town...BUT, there is another city about an hour away and I know they too have a strip club that offers amateur night and no one knows me there. It would be an extreme coincidence if someone saw me and beyond that, I could also travel further to other cities to complete this one. I consider this one a challenge but an acceptable one.
No. 5. - Although nerve wracking, this is possible. Knowing my bf, he would not be satisfied with just flashing my tits or something. Obviously he expects a performance and I intend to exceed those expectations. Still though, doable.
Completing this rather comprehensive list, especially to the standards that I know would be required would need some serious planning. I decided it was best to break it down into one task at a time and focus on that and that is how I will organize the re-telling of these stories - each one will be their own entry. For this first story I will recall task No. 1: Fucking a former high school teacher.
As I mentioned, I've been out of high school for some time and I haven't kept in contact with any former teachers, BUT there were two ways to go about this: The first is that I do have some of those busy body, go getter, casual acquaintances on facebook that did for some reason seek out and add former teachers over the years so I could creep them that way an initiate a conversation and work my seductive magic... or secondly - I do recall some years ago being at a bar and running into a teacher that I did have a small crush on in high school. I don't think he even recognized me fully but he did say hello and appeared to be mildly flirty. Also, out of all my teachers he was the cutest and had a bit of a rep for flirting with younger girls so this seemed like my best prospect. Lets call him Mr. H. for the purposes of this story.
I had my target in mind. I checked facebook and only a few high school friends had former teachers on there and none had this particular teacher. Ok, facebook was not going to work. I am a regular at the bar where I saw him last and haven't seen him since so this was going to be tricky. I placed an ad in an unnamed classified site specifically mentioning what I was seeking to do and at which high school I attended during what years...plenty of replies, however most fake and even if any were real, they were not who I was looking for. Hmm...frustrating. My last resort was to go to the school board webpage and see if I could find an email for Mr. H. Shockingly, this was quite easy to do and there it was! I composed a quick message.
"Hi Mr H. You probably don't remember me as its been sooo many years but I was a former student of yours between 20??-20?? at???? and I ran into you at???? a few years ago but was too rushed to strike up a conversation at the time. Anyway, its been on my mind lately and I just wanted to reach out and say hello and see how you've been doing! All the best - L"
Crazily enough I received a reply the same afternoon.
"Hi L! Great to hear from you and of course I remember! I actually remember seeing you at???? back in 20?? and I should have been more attentive to chatting with you at the time but it was a busy night as I had friends there, you were with friends and a quick 'hello' was all we could manage. I'd love to catch up though, if you are free. Let me know and maybe we can grab a drink and talk about the old days:)
P.s. Wish I could have had a dance with you that night!"
I wrote back:
"Hahah oh wouldn't that have been scandalous - a teacher drunkenly dancing with his former student?? I don't know if our city would ever survive. Here is my number?????????? feel free to text me and we can arrange that drink;)"
We ended up texting back and forth pretty much immediately and arranged a drink for the following night. I was pretty confident in my sexual and seductive capabilities but given that this was someone I knew a lifetime ago and in a professional capacity, this was new territory for me.
I chose my outfit carefully - not overly slutty but certainly revealing enough to pique his interest and casual. I wore black yoga pants and a tight white low-cut shirt with very short sleeves. My breasts are my best feature so I always show them off in tight low-cut shirts. We agreed to meet at a restaurant downtown and have drinks and catch up. When I arrived he was already there seated but got up to greet me. He smiled and said hello as we hugged and I noticed it lingered a bit and my breasts pushed into his chest. He took my hand as I sit, very gentlemanly yet quite forward and flirty too.
We got chatting about all the usual topics, work, high school of course and all the people we both knew, pretty surface level stuff. Every now and then each of us would say something flirty and at one point he touched my hand on the table. I was on my second glass of wine and we were talking about travel when he wanted to show me some photos on his phone so he came over and sat beside me instead of across. He sat very close and I leaned in to look at his phone. He scanned through a few photos and then I felt his hand on my thigh. I looked at him, our faces about an inch away, but didn't say anything. Instead, I parted my legs ever so slightly and he slid his hand inside my thigh in response. He leaned in and gave me a very soft kiss right on the lips there in the restaurant. I let it linger for a moment and then leaned back and asked if he wanted to leave.
As we left the restaurant he had his arm around me and suggested we just take one car back to his place as I'd had a few glasses and that he could bring me back to get my car later. I agreed and as soon as we were both seated in his car, I had no sooner done up my seatbelt when he had leaned over and kissed me much more passionately this time. He grabbed the back of my head and our tongues flickered in each others mouths for several minutes. I took one of his hands that was on my face and lowered it down my neck and over my cleavage and place it on my breast to let him massage through my thin shirt. His hands slid lower and run over my body and I again parted my legs for him and let his hands rub my vagina through my pants. I was quite turned on and getting wetter by the second. He broke off the kiss and suggested we get going. As we drove through downtown to his place, it seemed to take forever and I was so turned on at this point, I grabbed his wrist and pulled his hand over and put it down my pants so that he could finger my bare clit for the first time. It felt incredible, being in stop and go traffic getting fingered by my former history teacher. I actually came within seconds, squirming and moaning on his fingers as my pussy got wetter and wetter. I came down from my first orgasm but he left his hand in my pants and gently rubbed around my clit causing me to gasp now and then.
"Did you ever think, back when you were teaching me, that this could happen?" I asked when I calmed down again.
He laughed subtly,
"Well, you were definitely cute in high school, much sexier now and when I saw you a few years ago at the bar, I thought for sure I wished circumstances were a little different and then when you wrote me out of the blue - wow, that was just amazing."