The List

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."

At that moment I received a text from my boyfriend, I didn't want to be rude but I felt I should quickly reply. His text read simply:

'Where are you?'

'Just got fingered in my teachers car. About to cross no.1 off the list ;)' I replied, and put my phone away but immediately felt it vibrate several more times. He asked for this when he wanted his revenge on me so I figured I'd let it stew a few moments. We took the highway around town to Mr. H's house rather than drive through and I could see him glancing over at me as we drove.

"What's on your mind?" I asked playfully.

He glanced over at me and nodded towards my pants.

"Why don't you take those off?" he said.

I slowly slid my pants down, took my shoes off and removed them completely. I set my legs up on the dash and took his hand again and had him gently rub my wet clit. His fingers felt so good circling it and he inserted one in my vagina and slowly finger fucked me. I closed my eyes and leaned back in the seat trying to gyrate my hips against his hand.

After a moment or two I could feel the car decelerate somewhat and I heard him whisper,

"Look out the window,"

I opened my eyes and we were right along side a transport truck that Mr H. had deliberately slowed down right beside to show me off. I looked up and the driver was staring down at me smiling, my naked bottom half getting finger fucked by my former high school teacher. I immediately gasped and tried to close my legs but Mr H. wouldn't let me and told me to lie back and lift my shirt for him.

I looked up at the trucker who we were driving along in tandem with and he was clearly not bothered by the display. I hesitantly leaned back again trying to relax in front of this strangers and I lifted up my top and then my bra to expose my 36C breasts. Mr H. immediately took his hand from my pussy and ran it over my breasts, squeezing them and flicking my hardening nipples. I spread my legs wider and started to rub my pussy, I was so wet that I could feel my juices running down my thighs and onto the seat. I closed my eyes and masturbated in front of Mr. H and the trucker until I felt my orgasm building and I tensed up and squeezed my thighs together with my hand between them an came hard while being watched by these two. It was so hot having a stranger watch me cum while driving along the highway. I looked over and my former high school teacher was smiling at me. I brought my fingers to my mouth and tasted myself on them, sucking each finger completely clean.

I pulled my top back down and put my pants on as we drove off leaving the trucker to do whatever he was going to do, I wondered if he was masturbating while he drove...

Another few moments we pulled into the driveway of Mr. H's place, as soon as we got inside he pushed me against a wall and kissed me passionately while running his hands up my body and roughly squeezing my breasts, his lack of emotional conflict while touching a former student made me wonder if he had done this before. He placed his hands forcefully on my shoulders and pushed me down to my knees right there in the entrance halls. He didn't even wait for me to undo his pants, he quickly undid them himself and pulled out his hard cock and shoved it into my face trying to get it into my mouth as quickly as possible. It was fairly short but oh my god, so thick! I didn't even have time to get a hand around it as it was thrust into my mouth, stretching me as wide as I could open.

I wasn't sure I'd be able to get my lips around it and I protested a little with a few gasps and moans at his forceful ways but eventually I was able to get it in my mouth and he grabbed my hair and started literally fucking my face. I had to take a few breaks as he made me gag but he didn't allow me rest for long and kept moaning and mumbling dirty things while fucking my mouth. He reached down and put his hands down the front of my shirt and played with my breasts under my bra. Eventually he reached down, stood me up and lifted my shirt, I raised my arms to let it slide over my head and unclasped my bra right away, allowing my breasts bounce free.

His mouth was all over them in an instant, licking and sucking, covering my chest in his saliva as his hand was down the front of my pants vigorously rubbing my clit. My knees felt weak as I could feel my wetness soak through my panties and even my pants again. I wrapped my arms around his neck as he continued sucking my breasts and I braced for another orgasm. I screamed as I felt the flood of girlcum soak my pants and run down my legs.

As I came down from my orgasm I mistakenly thought I might get a break but he quickly moved me into the next room and pulled down my pants while turning me around and bending me over a couch. I could hear him unwrap a condom and snap it on and then seconds later I felt the massive girth of his cock at the entrance to my soaked pussy. He wasn't too gentle and thrust it in causing me to gasp in shock feeling my pussy stretch around him. He grabbed my hips and immediately began pounding into me harder than I've ever been fucked. If I was not already soaked, there is no way I could have managed it.

He fucked me hard like that while bent over his couch for at least half an hour, I rarely have guys that can go that speed for that long. I must have cum five or six times but my pussy was also starting to get sore from his thickness. I heard my phone going crazy in my purse knowing well that my boyfriend was trying to get a hold of me wanting details of my evening. It took a fairly good effort to get Mr. H to let me take a break but finally he removed his cock and I fell to my knees by the side of the couch, breathing heavily as he announced he was getting some water and would be back. I took the opportunity to check my phone, I was sweating profusely from the fucking I'd just had and wrote a quick reply to the numerous texts from my boyfriend -

"Looks like its going to be a busy night. Just got fucked HARD over a couch. He's way more comfortable with this than I thought and he might be into some rough/humiliation stuff. I'm going to be pretty late. Will send you updates later baby;)"

I felt my phone go off again just as I put it away and Mr. H returned, two glasses of water in his hands and this time completely naked and still hard, but the condom had been removed.

"Thank you," I said as he handed me a glass of water and we both took a minute to rehydrate.

We set our glasses down and he sat on the couch beside me and leaned down, kissing me hard on the mouth. He grabbed his cock in one hand and my hair in the other, leading me over to it. His forcefulness kind of turned me on and was totally contrary to what I imagined fucking my old teacher would be like. He again brought my mouth down to his cock and this time I was prepared for how thick he was, I took him all the way in and sucked deeply and quickly knowing now that he liked fast and hard. My head bobbed up and down on his cock for what seemed like hours and suddenly he grabbed my hair and lifted my head off his cock and put his legs up on the couch and spread them wide...this was new to me and I wasn't sure what he was doing until he forced my face down lower.

"Lick my asshole, baby." he said, which threw my off guard completely. I'd never done such a thing and had never even found myself in such a humiliating situation but the passion with which he demanded it and something about the moment I was in, I strangely found myself willing to comply. I grabbed his hard cock with one hand and looked right up at him, maintaining eye contact, I licked his balls up and down for a moment before maneuvering myself lower and slowly extending my tongue out to his asshole. We were both sweating and I could taste the salty flavour and everything smelled like sex as my tongue probed his hole. He moaned deeply and then I felt a hand on the back of my head and he pushed my face deeply against his asshole. I couldn't breathe for a second but then got the hang of it and inserted my tongue, flickering it around as I fucked his ass with my tongue.

It was by far the dirtiest, naughtiest thing I'd ever done. I tried to figure out the rhythm of tongue fucking his ass while I jerked his cock and maintained eye contact, it was surprisingly challenging. Again it seemed like a lot of time passed and I had to time my breaths when I could come up for air, he didn't allow me much time at all. Eventually he lifted my head and I gasped deeply, having my first proper breath since the ordeal began. I wiped the saliva off my mouth and chin and my eyes felt a little teary so I wiped them too. He put another condom on and stood me up, grabbing me by the waist and having me straddle him as I lowered my pussy onto his cock. Strangely enough the humiliating aspect of the evening had me very wet and he slid into me with ease. I began gyrating against him and within seconds I was wildly riding his thick cock, bracing myself against him and the back of the couch as I fucked to several more orgasms.

"Soon its going to be my turn" he grumbled into my ear as I rode him.

"Ya?" I said as I didn't even break pace fucking him. "You going to cum for me?"

He grabbed my breasts as I sat back and fucked him, he looked right at me and said,

"I'm going to cum right in your pretty face baby." he didn't even ask but just made the assumption which was obviously degrading but oddly hot to me.

I'm never surprised anymore when guys want to cum on my face, I must have one of those faces made for it. I would say 99% of requests for finishing are on my face. I'm ok with it as I'm always messy by the end of sex anyway but I always find the psychology of it interesting.