It has been a while since I’ve written about one of my sexual encounters, but that is because of the lack of sexual encounters. Nothing in this story involves me crossing something off the list, but I think you will all enjoy the story nonetheless. I recently met a woman online, who for the purpose of anonymity I’ll refer to as ‘Z’. In fact, she is the one who chose the moniker ‘Z’. Everyone goes through a dry spell, but there is hope and this is my story about overcoming it and the possible start of a new chapter for The Fucket List, enjoy.
The funny thing about meeting ‘Z’ was that I had just deleted all of my dating apps; I had planned on taking a break from it all until the new year. The last app I was ready to delete was OkCupid, but moments before I could, I received a notification that I had a match. I opened the app seemingly one last time to see a picture of ‘Z’. I looked through her profile and it seemed as though – based on her answers to the questionnaire – she was an open and sexual woman. I sent her a message and we began to talk back and forth until she gave me her number. We began to talk a lot over the next few days; trying to get to know each other better. We agreed to meet for a date on Wednesday night.
One thing you should know is I live in a fairly small town; a summer town – so in the winter there isn’t much to do. I mentioned possibly going for coffee since there were limited options. We ended up meeting earlier than that. I pulled into the wrong driveway and waited for ‘Z’, unsure of who was going to walk around the corner. I’ve learned in the past that pictures can be deceiving. I was surprised when she opened my car door and said introduced herself. She was better looking than her photos – not to say she wasn’t good looking in her photos. I only say this because people tend to manipulate the way they look in photos.
It was only five o’clock in the afternoon, but was already getting dark. We were talking and I had completely missed our turn and we ended up in some other town. I was surprised how open she was about the topic of sex. Many people can be quite open about it online, but in person they clam up. About five minutes after meeting her she brought up my blog and how she had read most of the stories on it and loved it.
Let me jump forward to the part you’ve been waiting to read. I decided we should go to a spot looking out at the water, but when we arrived there were other people there. ‘Z’ said we should find somewhere more private; saying she knew of a place. We drove to yet another town – three towns in one night – where she directed me to a provincial park. It was dark; not a single light in the parking lot and not a single car – it was perfect. I parked in the back corner; the furthest spot from the road and turned off the engine. There was a bit of tension at first – we were still a bit skeptical about the expectations. ‘Z’ used her phone as a bit of light so we could see each other and we continued to talk. Bringing up The Fucket List on her phone we went through the different list items and discussed them, until I made a move.
This move would have been made earlier, but just understand my car has a console separating us, so leaning in for a kiss can be a bit awkward. I leaned in and kissed her – momentarily missing her lips because of the damn console. We both laughed – I was positioned in such an awkward position. I suggested we try the backseat and without hesitation ‘Z’ agreed. I got out of the car, but she just maneuvered her way into the back seat. We kissed and she moved my hand to her breast. Then she asked “now what?” after a few moments of making out. I was speechless, I wasn’t sure what to say for a moment. I suggested it was up to her and that I was up for anything.
We began to shed our clothing; my sweater and her top coming off first. I reached around to unlatch her bra, but the bra got the best of me; they still confuse me even now. ‘Z’ unlatched it for me and revealed her breasts to me. Now if you’ve been reading my blog you know I’m an ass man, but I’m telling you her breasts could easily change my mind. She had perfectly round, perky breasts and small dark nipples. I couldn’t help but stare in awe, they were the best breasts I had ever seen in person. I squeezed them and leaned in to sucked on her erect nipples; burying my face in her chest.
I leaned back and the two of us removed our pants and underwear, my hard cock popping out of my pants, followed by my t-shirt. The two of us were naked in the back of my car in the middle of the Canadian winter; our clothing scattered from the front seat to the back seat. ‘Z’ suggested missionary and laid back; her legs opened and I immediately went down on her; missing the taste of a woman on my tongue. She taste fantastic as I sucked on her clit and fingered her. I could hear her subtle moans as I curled inside her. Moving up her body, she grabbed the base of my cock and guided me inside her warm, wet pussy. I began to thrust, however the car doesn’t offer much space and I had the top of my head pressed against the window and ‘Z’s’ head was tilted to the side. We didn’t do that for long before ‘Z’ made another suggestion; she was going to try being on top.
I moved up into the front passenger seat, ‘Z’ moved forward, but before making her way to the front she leaned down to my crotch and took my cock in her mouth. It felt amazing and I had full view of her ass bent over next to my head – her body was made for sex. I reached over and spanked her before squeezing her cheeks and she continued to blow me. She joked that she had to do that before getting in the front. As she moved into the drivers seat, her bare butt hit the steering wheel and the horn honked; echoing into the dark forest before us. We both laughed.
By this point the windows were steamed up and you couldn’t see outside. ‘Z’ positioned herself above my lap and sat down; her pussy sinking down over my cock. There wasn’t much I could do from that position because of the limited space, but I sure as hell loved it. ‘Z’ began riding me; my cock sliding in and out of her; her beautiful breasts bouncing against my face. I moved my hands all around her body; discovering it for the first time. “Your cock feel so good,” she said. My heart was racing as I had this beautiful woman on top of me; enjoying herself as she pleasured me. This was the position we stayed in the longest, but we both wanted more.
“We could try doggy in the back maybe?” said ‘Z’. I agreed and she climbed into the back once more; I followed close behind. She bent over; her head pressed against the back door. I moved behind her and slid into her. I was too tall for the backseat so my head was sort of turned sideways and pressed against the roof. However I was still sort of able to thrust into her; it was limited, but it was worth it to look down at her arched back and round, plump ass pressed against my waist. This position somehow managed to last longer than missionary despite me knee being in the cup holder.
We were both sweaty, beads of condensation drizzled down the windows; leaving streaks. I sat down, my back against the backseat door and without hesitation she went back down on me; taking my cock back in her mouth. “I just love sucking cock, I don’t know why,” admitted ‘Z’. I was happy to let her suck me as long as she wanted. Despite her saying it wasn’t the best of her oral skills because of how crammed we were, it was quite good; she is definitely orally talented. It was a weird sensation to have your entire body in a cold car, but your cock in the wet heat of someone’s mouth. A first happened for me, as she was sucking my cock she would take breaks and ask me questions about my writing. She was trying to get to know me better while going down on me. It was kind of endearing and adorable. Here I am in the back seat of a car on a first date, telling this girl more about me as she has her lips wrapped around my cock.
“Do you think you can cum?” asked ‘Z’. I had a feeling I couldn’t because of the cramped positioning. She laid back down and I played with her pussy and anus a bit. She said she considering masturbating and cumming and asked if that was okay – I told it her absolutely. She began to rub herself and I was absolutely turned on by her masturbating in the back of my car with me watching. She figured it would take too long and sort of decided against it and we ended up cuddling in the back butt naked until another car pulled into the parking lot. We got the hell out of there after getting dressed; trying to find our scattered clothes in the dark was another interesting challenge.
I took her home after and we agreed that we would like to see each other again. For those of you who have read my older stories, you’ll know that my one night stand I was adamant that you can’t really have good sex on a first meeting because you need to get to know your partners body. However this may have changed my mind on that because despite being limited we both had a really good time with some fun and pleasurable sex. I guess it all depends on the chemistry you have with someone. I’m excited to see her again and she is also excited to help me cross items off The Fucket List. I look forward to telling you more about ‘Z’ and my sexual escapades! Remember if you’re also on a dry spell, it will come to an end; just be patient because it may happen when you’re least expecting it.