I would visit Whaletail about once a week, often times twice, for no-strings-attached sex. Since we both disliked the feeling of condoms and she was on birth control, we got tested. I wouldn’t stick around long after we were finished, since other than sex, we had nothing else in common. It was a purely physical relationship and we were both fine with that.
The first time going to her house was a bit awkward, as she lived with her mom. I knocked on the door and was told to come in, and saw her mom sitting on a couch in the living room watching TV and having a cigarette. She seemed like a nice enough lady, and let me have a seat while waiting for her daughter, but other than that seemed uninterested in what I was doing there.
“Hi Yogi, come on back here”, Whaletail said when she popped out, hair damp from the shower.
“Have fun”, her mom said as we disappeared to her daughters room.
Whaletail’s room was always messy, with clothes all over the place, except the bed. She had a vast collection of clothes, which I found odd since I had never seen her in anything other than her uniform of crop tops and jeans when she was out in public.
“Is it ok for me to be in here with your mom outside?”, I asked, knowing that I had come to her house just to fuck, and I was raised to respect a persons house when you are a guest.
“Yeah don’t worry about it, she doesn’t mind”, she answered nonchalantly. She was wearing one of her tight tops with no bra, sweats, and of course her namesake look of a black thong above her waistband. If she wasn’t leaving the house, she would usually have sweats on. This was long before leggings and yoga pants were the look, but I imagine she would wear those now instead.
We got down to business quickly, and I finally got to suck on those big tits of hers. We’d make out and explore each other’s bodies, before arranging ourselves into a 69 position. Her being a taller girl meant we could enjoy sucking and licking each other at the same time, as it’s a bit more difficult to pull off on shorter girls. She was back to working her magic on my pole while I dove face first into her already dripping pussy. She was on top and I must have hit the right spot when she bucked herself onto my face so I could get my tongue in deeper, and I started to work up a rhythm.
“Put your fingers in my ass”, she said in a gasp, lifting her mouth off. I started to dip my fingers into her wetness, trying to gather as much lubrication as I could. I worked my index into her ass while doing long strokes down her slit, and while I don’t want to give the impression that her asshole was anything but tight, it was clear that she knew how to relax herself in order for my finger to slide right in.
“More! Harder!”, she moaned loudly at me. Two things went through my head at that moment. First was to start jamming my middle finger in her ass as well, second was that her mom definitely heard that. It didn’t take long for both of my fingers to be in her ass damn near to my hand, working them in and out at a frantic pace along with my mouth sucking her clit, and just a second after that she took her mouth off my cock and came hard.
She was not a screamer like Crazy was, but she also didn’t have volume control. She climbed off me and took a moment to breathe. My dick was rock hard and ready to go after her sucking.
After her moment of recovery was over, she got down on all fours. I didn’t need an invitation and got right behind her, finally getting to feel her from the inside. Despite how wet she was, it was still a struggle for entry. Shallow strokes getting progressively deeper until I was able to bottom out, and her loudly groaning as she got used to my thickness. I parked it there for a moment, letting her feel the throbbing.
“I want it hard, as hard as you can give it”, she turned her head to say. Well if that’s what the lady wants, I thought to myself. So I grabbed a hold of her hips and drove myself into her as hard as I possibly could, full force from the get go. The sounds that escaped her after that are something I’ll never forget. Forget just her mom hearing, I was certain her neighbors would complain.
I grabbed as much of her still damp hair as I could hold, forcing her back into an arch that allowed me even deeper access. Her ass absorbed every clash of our bodies, thundering loudly.
“Put your fingers back into my ass”, she yelled. I gathered a dollop of her wetness off of my dick with my thumb, and jammed it into her hungry asshole. She took it in completely to my hand, while her pussy got even tighter.
I warned her of my impending orgasm,
“No! Fuck my ass with your thumb”, she pleaded. I drove my cock and thumb into her as piston-like as I could, and a moment later she was moaning and clamping down on me with both holes in her second orgasm. My own soon followed and I could feel myself draining several full shots into her clamped pussy.
In the aftermath, she got up to use the restroom, throwing one of her dirty shirts at me so I could wipe up. Putting on only her black thong, she left the room.
When she came back, I tried to make conversation, but found out we didn’t have many common interests. She considered herself a skater girl (despite not knowing how to actually skateboard) and that definitely was not my scene. I realized it was pointless and decided it was cum and go. We dressed and she walked me out of her house, her mom telling me to drive safe on the way.
We would repeat this cycle for a while, and I learned a bit more about her friendship with Crazy. They had been known to fool around with each other from time to time, but maintained that they were simply best friends that helped each other out when in need.
Unfortunately, I would never get to fuck her in the ass, though not from lack of trying. It was something that we would attempt regularly, and since I had never done it before, she had to teach me how to do it properly. Only thing is, the way she knew was to lube each other up and jam it in, which is not the way to go about it at all. Nonetheless, her orgasm always seemed to require anal stimulation, so she got herself a toy before long that had a permanent spot in her rectum.
She was able to take me easier than most women, and my full length would reach her cervix exactly. I would say that this is due to her being in the tall side, but I’ve also had experience with a girl my own height who was considerably more shallow, but that’s another story.
Next time, flashback to Princess.
Source: reddit.com/r/gonewildstories/comments/6bw2r1/sticking_my_dick_in_whaletail_part_2_mf
Did you ever take a shot at the mom?
Did you ever fuck her with crazy?