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Freaky First Times
After spending 20 years in the US Navy, I have spent more than the average amount of time with more than the average number of ladies.
One lady in particular was a very aggressive sexual creature, she was over 10 years younger than I was, and loved sex in every way except swinging, and that was just because she had never thought of it before. We did everything a man and woman can do, semi-public places, every position, 5 and 6 times a day, in the bunk room when I was on duty, in her bunk in the barracks, etc, etc.
We finally ended up living together for about a year, and we continued to carry on a vigorous sex life, even trying a milder type of swinging. I still think the only reason she didn't try it was she wasn't sure I was serious that I wanted her to go ahead and fuck the other guy.
She also really loved anal, and I mean she had orgasms from anal, and insisted on anal at least once a day, and I made sure she got what she wanted. We also experimented with some mild bondage, and developed a very high level of trust in each other.
We would take turns tying and blindfolding each other up and then doing things to each other we had thought up or had not had the nerve to ask about before. Soon there wasn't much we hadn't done or tried. Well one time when it was my turn to be tied, she was sucking my cock (boy she was really good at that too), she started rubbing her finger against my anus, she frequently did this, but it was just teasing. This time was different, but I couldn't tell why I thought so, until I realized she had lube on her fingers, she slid a finger all the way up my anus, in one swift move, and started working my ass with her finger, all the time sucking my cock, never missed a beat. Then she started adding a finger about one a minute, until she had three and started to put in a forth, that was when it started to hurt. That was also when I came very hard. I very seldom cum from oral stimulation, but this did the trick big time.
When we were finished and cleaned up a little, we talked about this some, you see I decided I liked it, and she did too. She wanted to do more, and I felt I wanted her to try but I wanted to be sure she didn't hurt me, I also wanted to watch. After we talked some, she went and picked out one of her toys, a small vibrator, and some more lube, she untied me, so without any ties, or blindfolds, we went into the living rooms and I sat on the very edge of the sofa with my ass barely on the cushions, and my asshole exposed.
She began by swallowing my whole cock until I was rock hard, then without me ever even seeing her do any of this, she somehow put the lube on the vibrator, and had it pushing against my sphincter. She slowly pushed the vibrator all the way inside of me. The vibrator was thin but about 7... long, all the time still sucking my cock like crazy. Then she turned on the vibrator, I filled her mouth full of cum almost immediately, she came right behind me, without ever touching herself.
The next day we went to the local adult book store and bought a strap on for her to use. The dildo portion was bigger (but not too much) around and about 10... long. We couldn't wait to get home to try it out. We stripped quickly, and I brought her off with my tongue in seconds, she was so hot and begged me to make her cum quickly, so she could last long enough to enjoy this.
I told her, we would wait for me, because this was just for her, since I could tell how badly she wanted to fuck me with the strap on. We agreed on a safety word first, and then I got a large mirror, so I could see her, I knew she would want to fuck me doggy style so she could get the full effect. I got in position, and she lubed by asshole. I watched in the mirror, and her lovely face changed to one of pure lust, he eyes glazed (I swear) and she put the tip of the strap on inside my sphincter and started to slowly work it, but after about two small strokes, she slammed the whole thing fully into my ass, and fucked me hard with long full strokes. I thought my insides would come out through my mouth, it hurt like hell but I held on for about 5 minutes, because I wanted to give her a chance to get off.
I was just about to use the safety word when she came so hard she started squirting. She told me afterwards she had never squirted in her life, and let me tell you she flooded the whole bed. She came for almost a full minute and a half, squirting for most of it.
I love women that squirt, always have, always will, and over the years I have found that all women can squirt, you just have to find out what flips that trigger in them. This was her trigger, and it was just that one time, I ran into her about 10 years later, and she told me that she never had again, and she had used the strap on with me and other men frequently, but none were like that first time.
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