Before We Met

Much of what follows is laughably tame when compared to what our relationship has evolved to in the intervening years, but recently I asked my wife Cindy to tell me about some of her sexual encounters with her first full time lover, Teddy, before we met, and embarked on our journey.

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Cindy's words:

Here is one of my best memories about having sex with Teddy—especially on Sunday afternoons when we were living in Boston. We would go out for a walk along Commonwealth Ave. And when we returned to my apartment, I would take a hot bath while Teddy waited, reading in my living room. I would spend a lot of time shaving my legs, and I would soap my pussy while I fantasized.

I would think about his finger fucking me while I gently jerked him. This would lead to his giving me a good, hard fucking with huge cock. I would fantasize about locking my heels in the small of his back while holding him tightly inside my pussy while he shot a big, hot load in me. Usually, when he came hard like that, I could feel his balls emptying, and I would French him deep with my tongue, keeping my arms and legs wrapped around him until we felt as one. Then I would milk every drop of cum from his still hard cock—until he would start thrusting again, and we would start over. That was a lot of dick to wrap my pussy around, and I fantasize about it to this day.

During this fantasy, I would usually finger myself to a mild orgasm in the steaming bath. After toweling off, I would stand naked in front of the mirror spending a lot of time applying light makeup and combing my hair—sometimes even putting just a touch of rouge on my nipples. My pussy would already be swollen and tingling from the hot water and my gentle masturbation. Finally, I would put on a shorty bathrobe that barely covered my pussy, and I would walk out to join Teddy, sitting on my loveseat. I could tell sometimes that he had been fantasizing about what was to come because his cock was already swelling through his jeans. I would always make certain that I found a way to bend over in front of him before I sat next to him. I knew he loved to look at my bottom, and I loved to tease him with it.

At this point, we would usually get down to business quickly. He would embrace me and stick his hands inside my robe and gently rub my titties while he probed my mouth deeply with his tongue. It wouldn't take long for my robe to fall away, and I would offer no resistance as he started rubbing first the outside of my pussy, and then starting to further loosen me up with first one, and then two fingers. I would then start rubbing his cock through his jeans before I unzipped. Pulling his cock out would bring it to full attention with just a little stroking. Often, I would tell him that he could "put another finger in" my pussy, and that was usually a signal for him to start fingerfucking me vigorously. This would make me cum again—this time very hard.

At this point, my pussy would be pretty lathered up, and I would be ready to take his big dick without any more foreplay, which is saying a lot. It never failed to take my breath away when he would ram his cock into me all the way. I never measured it, but he could have easily held his own as a porn star. To this day, I compare his cock favorably to some of the guys on the screen, and it really excites me to remember his fucking me. I would guess that it was a little under 9 inches long and nearly 7 inches around.

After cumming hard from fucking his three fingers, I would still be extremely hot and ready to take a good pounding from him and pound my pussy he did. The sounds of my moans and screams would echo off the plaster walls, sometimes I would be embarrassed by the knowing looks that I would get from my neighbors. Sometimes, I would get drunk and even more uninhibited, and command Teddy to "Pound that pussy with that big fat dick." Sometimes, later when we were out in public. He would make me whisper those words again- just to embarrass me, and I could watch his cock swell as I said it again, but to be honest, it would get me hot too.

Teddy would tell me that it really turned him on to have me command him to fuck me in different positions. So sometimes when I was drunk, I would lead him over to a door mirror, lean up against it with one hand, stick my butt out, and spread my pussy lips to help him in while commanding him to "ram that pussy".

One time, while we were fucking standing up and facing one another, I was sober enough to notice that his cock was really dripping from my juices when he pulled out to shoot a hot load unto my stomach. It didn't take very long to for him to jack himself off rubbing his juicy cock on my stomach. Then, after he had shot a heavy load on me, we would hold each other tightly while he continued to thrust into the sticky mess on my stomach.

Since I was crazily not on birth control, and neither of us liked to use rubbers, Teddy normally shot his cum on me. Sometimes after a long night of love making, I would be covered in cum. I didn't like for him to come on my face, but depending on the position we were in, I would have fresh or drying cum on my butt, my back, my stomach, my tits, and sometimes, he would shoot as far up as my throat. Some of this was his youth, of course, but he could really shoot a lot when he was excited. I still really miss some of those hot loads firing out at such a distance.

All in, it was great sex, and I loved every minute of it. I still fantasize about his big cock when I masturbate. I love my husband and want to keep my marriage, and it is probably not practical to do this with Teddy again. But sometimes I miss that feeling of having my pussy filled completely. And regardless of how unrealistic, and with Teddy or not, I would love to find a way to get a long, thick cock back into my sex life.