My name is Carol. You do not need to know more about me than that. I am 32 years old and I have recently had a sexual awakening. I know, kind of old for that. Here is my story.
I am divorced from an early marriage, pretty typical. I have a nice condo that I received in the settlement. Actually there was very little equity in it at that time, so what I really received was the mortgage. I have an unexciting middle management job that I could tell you about, but I don't want to lose readers.
My social life controls my sex life so not much has been happening. I have hooked up with a couple of guys over the years but nothing serious. The sex was plain vanilla, just like in my marriage. Seems like a lot of guys think a few pokes in the vagina, an ejaculation, and a snooze take care of it.
I have been longing for more lately, maybe because I am 32 and some people say that age is the peak of a woman's sexuality. I got turned on to internet porn, and surfing around in it I discovered anal sex. Not only had I never experienced it personally, I had never even thought about it. Now it is all I think about. I will admit it has become an obsession, but I don't think I am ready for counseling.
To use an old expression, it blew my mind. I would watch some guy with an enormous penis shove it up some sweet things asshole and fuck her silly. Some of the women would try to act as if it hurt and it was their first time, but give me a break. They are not very good actresses and it was obvious that one, it did not hurt, and two, it was not their first time.
But that was OK, it was still a tremendous turn-on for me. I would masturbate as I watched and it always gave me a good orgasm. I bet there are some men reading this that are surprised to learn that women watch porn and masturbate just like they do. I am also sure that most women readers are not surprised, because they do it too.
As they say, 90% of people will admit they masturbate, and the other 10% are liars.
As time went by I wanted to experience nasty, dirty sex like that, instead of just fantasizing about it. I was not about to hire a male prostitute to sodomize me, so I needed to have a different solution.
I have been seeing a guy named Bob for a few weeks. We had not had sex yet but it was clearly on the horizon. I wondered if I could entice, cajole, or persuade him to do it to me. You would think that would be easy, because from what I have seen, the men are wildly aroused by it. The porn stars are required (I guess) to pull out before they cum, and they typically produce a huge load of semen. Sometimes it spurts into the woman's open mouth, and sometimes it shoots all over her face and hair.
I always found that disappointing because I am sure they both wanted it to go as far up inside the woman as possible. But the porn producers are aware of their audience and they know they have to prove that the man really did cum. Strange, because why wouldn't he cum? Fucking a woman's tight asshole must be pretty exciting for them. I know it would be for me. Oh, that sounds weird doesn't it.
But if I was a man I would definitely fuck women in every way possible. I have tried to imagine what it would feel like to push your stiff hard-on up a woman's warm tight asshole while she made little whimpering noises and begged you to stop, and then begged you to not stop. Wow, I am getting turned on just writing this.
My woman's intuition told me that Bob was going to put the move on me to have sex with him soon, probably the next time we got together. I resolved to somehow, someway, get him to fuck me anally. I didn't have a specific plan, just a general idea to not take no for an answer. We had a date to meet at our favorite local club, no big deal, just a few drinks and laughs. I drove to the club and met him there as we had arranged.
To keep this story moving I will cut to the chase. It was about 11:00PM and we were clearly starting to think about leaving when he asked me if I would go home with him. I didn't want to do that and feel trapped in his place, and I also didn't want to invite him to my place.
I said "Why don't we get a room? That way we are on neutral ground."
He was kind of surprised because he thought he would have to seduce me in small steps. Here I was blatantly saying let's get a room and fuck.
"Great idea, I will book it." He wanted to quickly agree before I changed my mind.
He whipped out his smart phone and did a quick search, and called to reserve a room. I asked him where and it was a decent place, not some flea bag. He does have redeeming qualities.
We drove separately with me following him. I liked that idea because if this did not work out I had an exit strategy. He did too, I thought sheepishly. He might think that I am not that great a prize when I ask him to put it in my ass. Although if my plans come true he might have a very good time. He went in the lobby to pay and get the key, and we parked side-by-side.
Bob led the way up the stairs to our second floor room in the motel. He unlocked the door and we went in together. There was a moment or two of awkward silence, and then he motioned toward the bed. I moved toward the bed and began to remove my clothes as I walked, and he followed suit. Soon we were both completely naked and we embraced.
We were not lovers, not yet anyway, so this was kind of fumble, stumble, but we got through it. We could at least express some affection, we are not barn animals after all.
He reached for my crotch and caressed my warm, wet pussy. I grasped his cock which was growing bigger and harder as I stroked it. It was thick and long, much longer than any I had previously experienced in person. Almost the size of the freaks of nature in the porn videos. When it was fully erect I took a good look at it. I would never do something so rude as to measure a man's cock but I estimated his to be between eight and nine inches long, perfectly straight, with the foreskin pulled back to reveal a beautiful head.
I traced the length of it with a feathery light touch, almost tickling it. I softly said "Big head!"
I didn't mean for him to hear that but clearly he did, so I said "Not you. This!"
I squeezed his cock and giggled.
I started to have second thoughts about taking it up my virgin asshole, but I had seen countless numbers of women in the porn videos take even larger cocks up their ass, and no one died. So why not? I suppressed my apprehension and moved ahead with my plans. I knew from reading about anal that once he gets past the tight entrance it should be OK.
Bob of course didn't know what I was planning, so when we got on the bed together he continued to fondle my wet pussy and was obviously preparing to fuck me vaginally.
I reached down and guided his probing finger to my anus. He looked at me with confusion as I tried unsuccessfully to insert his finger in my asshole.
"What are you doing?"