21/10/2024
So, I am not a great writer, but here goes. My name is better left unsaid, but I did have a nickname for a while, some called me Ace. I once had a huge crush on this girl, we had our ups and downs but were always friends, never anything more. We did hook up a few times for the couple years we were hanging out, all under different scenarios and circumstances.
Each time ended with a “we can’t do that again” from her which is not what I wanted to hear.
Who’s this girl? Well to me she was the fittest girl I had ever met, incredible hair, tits to make any guy forget what they’re doing to stare at them and unfairly pretty. She also happened to be full of character, funny, lively and easy to get on with. It was all so impossible to resist, and she knew it. We can call her Tess.
At some point we decided to live together, this was after we had slept together a few times and after we fell out way more than a few times. When we moved in together, she made it super clear that we couldn’t hook up again.
While I did agree to this in principle I definitely didn’t like that, I wanted to live with her for fun, to move away from my house, for loads of different reasons. But also, it was a bonus that I was closer to her. I figured I would get to see her in a different light and maybe with less clothes on. I hold my hands up, a couple pervy reasons for wanting to live with Tess.
I will probably tell you about the other times we slept together. But this story is about how it happened in the flat, well one of the first times we fucked in the flat, months after moving in. Now keep in mind she was super open about her sexual habits. She would tell me she was going to watch porn for example, which obviously meant I would be in my room wanking trying to picture her in her room.
Months of watching her walk around with just a top on, nipples visible with no bra. Months of knowing she was fucking herself in the room next to mine. Months of frustration building and building. Not to mention the odd time I gave her a massage. Most of the time when I massaged her I got nothing, but that doesn’t mean I didn’t like it.
I got to touch her, see her bum and take mental pictures for later. Each massage was slightly different. Sometimes I was allowed to take her bra off, sometimes it had to stay on. Sometimes she kept her jeans on, sometimes they were off. Sometimes I couldn’t touch her bum, but very occasionally I could spend hours massaging ONLY her bum.
So anyway, we went day drinking in a nearby seaside town. Tess had this very tight orange top on and a short black skirt. I could tell her mood was a little different but that was nothing new, every day was different with her. We ended up at a pub and were talking about random stuff as always, but I could tell she was a little less defensive, a little more open. She asked me if I wanted to give her a massage when we got back to the flat.
This wasn’t the first time she asked, although it was usually me offering, she did ask occasionally. I obviously said yes, especially as she said it with just a little ounce of sexiness, not enough to be obvious but just a hint of a clue. Now this is Tess, she did like to tease me so at this point I just figured I might be lucky enough to take her bra off and that’s probably where it would end.
When we got back to the flat, I specifically didn’t mention the massage, I wanted to see if she would ask again. Lucky for me she did, I would have mentioned it later, a huge gamble from me that paid off, I wanted to know that she actually wanted one. She had the bigger room of the two and every massage was on her bed. We went in and she told me to face the other way, not that she really did much. She took off her top but everything else stayed on, much to my disappointment.
As she laid down, face down onto the bed, I got onto the bed and took up my normal position, which was essentially sitting on her bum. She still had her skirt on as well as her bra. I put oil on her shoulder and began to massage her back, neck, shoulders and arms. Now, I had been in this position a couple times before but at this point it had never ended in sex, the times we hooked up before did not start with a massage, this wasn’t the last massage fuck though, luckily for me.
I would always be slow and test the boundaries as I went, frequently leaving 5 to 10 minutes between each test, inching my way to different areas of her body. Putting my hands under her bra after 20 minutes of massaging her shoulders was always a little test to see if she would take it off was always the first test.
As I continued to massage her, she reached behind to unhook her bra “I will get this out of your way”. Jackpot, or at least up until that point I thought. I know you’re thinking that it’s just a bra strap but keep in mind I fantasized about this girl most of the day. Here I was looking down at her covered in oil with my hands just a little more free. I had to be careful, I didn’t want her to know I was hard so I had to move just a little so she couldn’t feel me.
Although the bra was still in place with the straps off I could see her side boobs either side of her, that’s right they were that big.
It had been about 30 minutes of massaging her and I decided to focus on her sides. Pushing my hands up from a little above her hips to her arms each side, I didn’t do it with every pass but on the odd occasion I would wrap my hands around a little more to feel her tits. I was so concerned she was going to tell me off, but she didn’t. Well she didn’t say anything until one of my hands was wrapped around so much I got close to her nipple, she said “that’s a little too close” so I figured that was my line.
She hadn’t let me get that close before with other massages, so I went back to her shoulders, neck and arms. Over so often going back to her sides, I couldn’t stop myself, I wanted her boobs in my hands, even if it was just a little.
The next test was her bum. I had massaged her legs, bum and hips before, but she didn’t always let me. I very cautiously asked “do you want me to go lower” and she very quickly said “yes”. Like previous times I moved from sitting on her bum which was a huge relief because I was so hard, and I am pretty sure she could feel me. Her black skirt just about covered her bum, which was the most amazing view, as normal I started on her legs. I had to sit between them so she had to widen them for me just a little.
So here I was looking at Tess’ bum, running my hands up and down her legs. I had wanked over her pretty much exclusively for months and this was an image that I knew I had to remember. She could tell me to stop at any minute and I would be back in my room cock in hand thinking about that view and what I wanted to do to her. Whenever I massaged her legs I would add a little bit of bum as time went on. As I ran my hands up her legs towards her bum I left my thumb on her inner thigh just a little longer too, with every time I did it.
She loved teasing me but this was my chance to at least try to tease her just a little.
I eventually had my hands under her skirt and under her underwear massaging her bum. I was so hard. I had shorts on so for a couple of seconds at random moments I would reach up my shorts to reposition myself or jerk my cock. All I wanted to do was fuck her but the best I thought I would get was being able to grab her bum, while I had second long wanks. With that thoughts she reached behind to lift up her skirt, showing her entire bum. I felt dizzy as I got harder, but it didn’t stop there. She had French knickers on which wasn’t abnormal but she pulled them in to make them look more like a thong. “Easier if these are out of the way” she said.
I must have almost fainted. This was the best massage ever, I couldn’t believe what was happening, dreams were coming true. Literally dreams. I had day dreams about this and actual wake up rock hard night time dreams. I don’t remember but I am pretty sure my second long wanks turned into a little more. I couldn’t help myself.
It was time to take risks, I still didn’t think I would actually get to fuck her again, it had been so long since the last time we hooked up and she had made it so clear it wouldn’t happen again. I decided to see how close I could get to her pussy, I figured if I inched closer she would tell me to stop, I couldn’t just go straight in, I had to take my time. I focused on massaging her bum and thighs and ignored the rest of her body for the time being.
I continued massaging her for 10 minutes, running my hands up her thighs getting closer to her, each time I got closer she moved a little, she widened her legs a little, she didn’t tell me to stop. The first time I touched her underwear covered pussy accidentally, it was just a grave but it made her jolt just a tiny bit, she let out a tiny moan that I could hardly hear and she was wet. Her underwear was a little see though, lacy, which made it hard to see if she was wet but the second my thumb grazes that area I could feel it. SHE DIDN’T SAY A THING.
I then spent 5 minute massaging just her bum, every 30 seconds or so I let my thumb move up her pussy, and she wasn’t stopping me. I did not know what to do. I was at a loss. I felt like she wanted more but we had fallen out so much about me wanting to fuck her, there was still a danger of this going wrong. All I knew was that she was very wet and was letting me touch her, all be it while her underwear was on. She said “are you hard” and I just said “yes” but she said nothing more. I went back to massaging her whole body so I could lean forward to reach her shoulder. As I leant forward it meant that my hard cock was pressing into her bum, I wanted her to feel me. Then I would go back to her bum, I couldn’t stay away.
Eventually she told me to pull her underwear down. “Take them off” she said and I couldn’t respond. I just slid them down her legs as she lifted her hips just a little. I could have cum in my boxers. Her skirt was still on and I continued to massage her bum, all I wanted to do was slide my cock inside her. Now reading this you will think obviously she wants to be fucked but I had to know for sure, all hell could break loose if I got this wrong. As I massaged her bum, I let me thumbs touch her pussy more and more. Eventually my thumb was inside her, just briefly and then it went to her clit, again briefly. I went back to her bum but the next time my thumb was close she moved her hips over to make sure my thumb was back on her clit. My hand went to my shorts, I unzipped them and got my cock out. I had to wank while I had this view.
My right hand on her, with my thumb rubbing her clit. My left hand sliding up and down my cock. I told myself not to cum, but it was so hard. She looked incredible on that bed, underwear off, skirt pulled up but still covering a little of her bum. I moved my thumb from her clit and slid a finger inside her. She moaned just a little but didn’t attempt to stop me. I knew from one of the previous times we hooked up that she liked my tongue work. So that was my next move.
“Do you want my tongue” I asked with a broken voice no doubt. “Yes” she replied. I moved a little, but I wanted to keep wanking. I couldn’t resist what I was seeing. As I moved, I took my boxers and shorts off. I didn’t want her to know what I was doing and had to be quick. As they came off, she raised her hips just a little. I laid down on the bed, one hand between her legs with my thumb back on her clit, the other on my cock. My tongue slid inside her, the taste, I loved it. I could eat her pussy for days.
I kept my thumb on her clit, in circular motioned playing with her, only moving it so I could use my tongue instead.
I went down on her for as long as she wanted. She could have asked for my tongue any second of the day and I would have been between her legs, I was not going to stop willingly. I didn’t know when I would get to taste her again so as far as I was concerned, I was setting up camp. Eating her pussy and stroking my cock. To my surprise though my tongue was about to make her cum, my tongue was inside her as she pushed back against it. “I’m going to cum” she said so I just kept doing what I was doing. Feeling her push against me, my tongue deeper inside her as she jolted on it.
I thought it was all over, I’d made her cum with my tongue before and it did not end in me fucking her. But this time, this time she pushed back onto all fours. “Fuck me” she said as she pushed her body against my cock, before I knew it her hand was on my cock between her legs. She guided it to her pussy and then pushed back against, I held her hips and pulled her in. Watching my cock slide inside her was incredible. I knew I wouldn’t last long but I was determined to get as much out of this as I could. I have never wanted to fuck someone as badly as I wanted to fuck Tess in that moment. I watched every time my cock slid inside her.
I kept fucking her, I couldn’t be too fast because I knew I would fill her with my cum. I was borderline at all times. I reached over to pull her hair as I slammed into her, pulling her head back, I got harder, one hand in her hair and the other still massaging her bum. It was still covered in oil and it looked amazing.
The odd spank and grab. I was about to cum so I stopped, I wanted to fuck her with my tongue instead, it was the only way I could think of to buy me more time. After eating her pussy for a minute or so I went back to fucking her. The girl of my literal dreams was bent over waiting for my cock. I pulled her hips back, sliding her pussy onto my cock. I was so deep, she was so tight, I didn’t want to take it out of her. I continued to slam against her, she moaned more and more. Holding her hips and making sure she got every inch of my cock, pulling her back against me so I was as deep as possible, she was so wet.
She put her bra back on while I was fucking her and then pulled off me. She moved as if she wanted to sit on me, so I laid down. She grabbed my cock and sat on me. Sliding down onto my cock I knew I had no control left, it was over, only a matter of time until she was going to make me cum. She could not have looked better, a princess, an angel, a devil, a barbie doll. To this day a prettier girl has not sat on my cock. Her hair a mess but still somehow perfect. The only issue, her boobs were behind her bra. I began to massage them over her bra. I knew she was going to make me cum.
Tess could ride my cock like no one else has since. It was true riding, rocking, grinding, gyrating. I pulled her bra down, I wanted to look at her perfect tits when she made me cum. It was the best view and to this day it hasn’t been forgotten. I really wanted to cum inside her, I knew it would be so much cum, I had been hard for over an hour at this point. I was desperate to pump my cum into her, I wanted her to feel it. But I knew she would be mad. All I could do was watch, I was powerless, my cock somehow still getting harder inside her.
I grabbed her tits for one last time, I knew I was close, I wanted her nipples in my mouth but that would have to wait for another time. She was about to make me cum. Rocking back and forth I couldn’t hold it any longer, my cock had never had this kind of ride, I had to tell her to get off, much to my regret, I wish I had pumped it all inside her. But instead, I exploded just as she took my cock out. Covering both of us.
“We can't do that again she said”…. But we did fuck again, and it only got better.