The second grand orgasm i witnessed (M/F)

[Utarhill]

This is the story about the second time I witnessed a squirting orgasm, and it was in bondage.

My ex-girlfriend, Jennifer, is the person with whom I really discovered the pleasures of BDSM sex. In the 13 months we spent together we experimented and tried a lot of things.

One of such occasions was the time I managed to give her a second squirting orgasm.

We were at my home; she was going to spend the night with me, and we were getting ready for the action. She had brought her military uniform (she graduated from military school and had to do weeklong training tours on a faraway base once every 6 weeks with this uniform) and wanted to do naughty things with it to get revenge on the military school and the officers/teachers (she hated every second of it but stayed because of the potential benefits and particularly hated an official who was mean just for the sake of being mean and you could tell she hadn’t get laid in years).

So, we prepared the bondage.

I readied some red and white handkerchiefs for the gag and blindfold, shoelaces for the wrist’s bindings and a 6’ rope (that she borrowed from her house, and it was used to hold the curtains in the summer) for her tits. She put on her uniform, which consisted of an olive-green button up blouse and pants, a military cap of the same color, a black utility belt (it had 2 pouches and a holster that was never used), and a regular belt to hold the pants. We set up the scene and put all the bondage gear on the bed for ease of access. Since we were roleplaying a military guard getting r@p3d by a thief I put on a mask (I got a medical facemask from my job) and grabbed a “knife” (a repurposed piece of a toy sword that I still had). I turned off the lights and the game began.

I approached her from behind and handgagged her with my left hand, while threatening her with the “knife”. I then disarmed her (took out her utility belt and groped her a bit in the process). She started to struggle playfully (in retrospective, it may have looked cute, or very creepy, because of our height difference), and I “threw” her face down on the bed (taking care that her face landed near the handkerchiefs) and jumped over her. I then gagged her (with a knotted cleave with the red one) and blindfolded her and tied her hands behind her back. When I finished, I spanked (softly and quietly) her a few times and sat her on the bed. Then I tied the big rope on her chest to perk up her tits through the blouse. I groped her for a bit, while kissing her neck, and she struggled a little bit. Then I pulled down her pants and panties and made her lay face up on the bed. I spread her legs and started eating her out. She tried to struggle, but she was enjoying it too much and couldn’t keep playing the role.

I then put her face down and just penetrated her raw (we didn’t have a condom and she had started taking anti pregnancy pills the month prior, plus going in raw made it look more r@p3y). I kept pounding her pussy in that position for a while, then I rolled her on her side and kept at it while groping her tits. At this point her cap fell off and also did the blindfold. She suddenly remembered we were roleplaying so started struggling again, and a small accident happened.

With the coming and going and her squirming my dick got out, and when trying to quickly get inside, I found the wrong hole. She writhed in pain as I went almost an inch and a half inside her ass. I pulled out immediately and started apologizing, but she, once her butt stopped aching, asked me to get clean and resume the game. I wiped my penis with a lot of sanitary wipes and toilet paper and resumed, putting all the effort I could, this time in doggy stile and face down and putting the cap back on.

This went on for a couple of minutes, till she just tried to jump away of me, but I just grabbed her and pinned her down to bed, while I finished her. I could feel the hot liquid coming out of her pussy and wetting the side of my bed and the floor. I then finished over her ass cheeks. I untied her and we just lay on the bed side. I took us half an hour to recover from the experience and start cleaning (which took us another half hour and several sanitizing wipes and a lot of toilet paper). After a thorough cleaning and changing the bed sheets (which we had to awkwardly disguise it in the morning as if one of us dreamed with waterfalls and toilets) we cuddled till we fell sleep.