The first time I roleplayed (M/F)

[Utarhill]

This is the story of the first TUG where I roleplayed.

When my ex-girlfriend Jennifer and I were about 4 months into our relationship, we decided to try something we saw in a crappy korean movie (can’t remember which one).

It was the scene before the climax of the movie, in which the MC’s love interest got tied up in bed, handcuffed and then tied with a rope to a pipe that went over the bed. The woman was also gagged with an OTM and blindfolded. In the scene she almost got r@p3d by the bad guy and was saved by the MC. This scene got Jennifer intrigued, and it was what later lead to her having her second squirting orgasm.

Prior to that, all our TUGs were pretty much the same. I would just tie her up, in more or less creative ways, have some foreplay, maybe some spanking, maybe she would practice sucking me (she never got it right though) or maybe I would just eat her out and then just get to it. While I did have a lot of fantasies and ideas, she had just discovered BDSM through me, and while we experimented a lot, I was trying to keep things at her pace so I wouldn’t hurt her physically and/or mentally.

Usually, it was I who would bring the idea of trying something new, but this time, she was the one to ask for it. She wanted to roleplay. She wanted to roleplay that scene from the movie, but without the hero arriving in time.

Now, for me this came as a complete surprise because every time there would be a r@p3 scene on a movie or show, she would close her eyes and turn her head away (she wasn’t abused or anything in that matter, but it caused her great discomfort nonetheless), so suddenly having her telling me that she wanted to roleplay that scene was surprising on the least.

After I recovered from the shock, we had a conversation about how we would do it and planned accordingly. We gathered our bondage supplies (such as two pieces of white cloth for the gag and the blindfold made from one old t-shirt), including something that we shouldn’t ever have used: a thin hemp rope taken from a potato sac, that had the same flaw that every hemp rope in Cuba had, it had a tendency to simply get very, but veery tight with little to no effort, making it extremely hard to untie.

After a week or so, we were ready, she picked up a nice outfit (a black blouse and black pants), like the one in the movie (it was great coincidence that she had one like the one in the movie, because that was also the same one she was wearing when we first met), we decided that we would do it in my house (another bad decision considering my bed didn’t had a bedframe).

The day arrived, and we were both overly excited about it, though we would necessarily have to wait until nighttime to be able to do it. When it finally was time, we closed the door and started to prepare for the action.

She dressed up and mentally prepared herself for it. We played the kidnapping using a cloth covered in “chloroform” (cheap after bath cologne) and proceed with the bondage. I first tied her hands up front using the hemp rope (which was a mistake) and left what I thought was enough slack to try to tie them to one of the legs of my bed. After a few tries, we realized that it would work as the rope was too short, even tying a shoelace to extend it. Then I had an idea. Over my bed there were my windows (which spanned the whole wall), and each individual window had a spinning handle. I tied the slack to the handle, tested it with a few pulls to see if it held and she said she liked that idea, because it made it look more like the movie (it made her hands hang over her head and she needed to keep her arms extended to be able to lay in the bed). I then gagged and blindfolded her, turned off the light (there was enough moonlight to see what I was doing) put on a condom and pulled down her pants.

I started eating her out and she started squirming (as did the actress in the movie). Until this point, everything was okay. I then proceeded to penetrate her, very slowly, and then I started thrusting, also slowly, as she liked when I started soft and slowly build up speed.

I started gaining speed in my thrusts, and she started squirming more and more. Because of the few sounds she was making I knew she was enjoying it, so I kept at it. She then forgets to keep up with the roleplaying and the fact that she’s tied up to the window and tries to hug me (when I would tie her hands up front, she would do this to change position almost seamlessly). She tries with all her might to do it, and then shit hits the fan. The knots in the hemp rope simply gave up and kinda turned into a slipknot, painfully tightening the rope against her wrists. She started to writhe in pain, which I interpreted as just taking more seriously the roleplaying, and she just panicked and forgot our signal to stop (snapping her fingers). This kept on for almost a minute, until she remembered that an otm is just a decorative gag and asked me to stop, almost crying.

Since this was our first time roleplaying and were over aware that anything could go wrong (and knew the fact that, from previous experiences with her, she could have forgotten the signal to stop), I immediately pulled out and asked what was wrong. She started crying and said her wrists were hurt. I started untying her hands, first from the window and then the wrists, and since the knots had moved and twisted, it took me about five minutes to finally free her (from that point onwards I always kept the safety scissors in the room when playing a TUG).

After that we cleaned the room, and I spent the rest of the night nursing her wrists and hugging her. On the morning, she had ropemarks on her wrists, so she had to wear her bracelets on both hands (she usually wore 4 handwoven bracelets on her left hand) during all morning and afternoon to disguise them.

The funny thing is that, after a bad experience, one would think she would just stop wanting to try things for a while, but when we talked about it the next day, she said she wanted more.

And since she had all the time that I was spending nursing her to think, she came up with a list of ideas to try. (policewomen, nurses, doctors, schoolgirls, maids, secretaries, there was so much that she wanted to try)

She also asked me to get rid of the hemp rope, which I did even before she asked me to.

The first idea we got to try (because it was the one that we had all that was necessary to perform it) was the one that became our most played one and eventually led to her second squirting orgasm (the r@p1ng of a female soldier/guard).

[Flyingvulture]

Great story!
Thank you for sharing, glad she wasn't scared away by the experience but rather willing to keep on trying.