Gerald & Carol (Part One)
When I was 25 years old I met this really sexually-perverted older woman who had all sorts of nasty, dirty ideas about sex—or so I thought at the time. I didn’t find out about this until we had been dating awhile. As turned on as I was by her I was shy around such a beautiful woman as she, so I didn’t make a move. I told myself that I didn’t want to scare Carol away by coming on too strong. I didn’t think to ask her for a kiss for fear it would offend her.
Of course I was an idiot not to recognize the signs. Her constant touching of my arm or my waist. The fact that Carol never wore any bra or —I suspect in retrospect—panties. She would rub her tits up against me at every possibility. I could feel her long hard nipples very clearly.
I finally clued in when we were at a beach and she kept touching my ass. At first it was just stroking my cheeks. Then the touch became a little firmer—like she was kneading dough or something. I have been told by several women that I have a very sexy round butt. I don’t know about that, but I do know all my bicycling to work over the years has made my legs and ass very muscular.
I was kind of embarrassed that time we went to the beach because Carol made me wear a very revealing Speedo swimsuit. She said it was a present and it would be rude for me not to wear it. I didn’t notice at the time that when the white fabric got wet it was almost transparent. But I still think everyone at the beach was staring at Carol whenever we walked out of the water. She was wearing the smallest bikini I have ever seen! I couldn’t believe she was wearing a thong in public!
At one point we were standing in water deep enough to come up to my belly button. Carol was facing me with her hands on my hips under water. Carol slowly began to stroke my ass. Only this time her fingers sort of wrapped around my cheeks so that her fingertips were deep in my crack. You have to remember that I had no sexual experience at this time (I was a virgin until I was 25 years old) and I definitely didn’t think of my asshole as being an erotic zone. That was for gay people to enjoy not a 100% straight guy like me.
Carol pulled my hips against hers and kissed me. I was shocked. The minute her tongue forced itself into my mouth I could feel my dick getting hard. I’m sure she could feel it too because she started moving her hips side to side. Soon the head of my cock had grown past the waistband of the Speedos.
We kissed for a really long time. I had never been kissed so deeply and passionately before. When we broke our kiss, Carol told me to do to her ass what she was doing to mine. I moved my hands down to her ass cheeks and started stroking them.
Now I could feel her hands at the waistband of my Speedos. She was pulling them down! “SHIT! What happens if someone sees us?” I thought to myself. Carol didn’t seem worried and soon I could feel the cool water surrounding my cock and balls.
She took her right hand and started jerking my cock off while her the fingertips of her left hand rubbed my asshole. It was electric! I started to moan but she quickly started French-kissing me again. I didn’t want to pull down her thong so I just moved my hands under the tiny piece of cloth. As I moved my hands I spread the cheeks of her ass.
Carol was practically sucking my tongue down her throat. I could tell she was really liking what I was doing. But it wasn’t enough. She stopped kissing me at one point and whispered in a husky voice to push my fingers into her asshole. I had nver done this before as I had heard women hate anal sex because it hurts them.
At this point her stroking of my cock slowed down and her grip became tighter. I was fully hard now. With her other hand she did more than just trace a circle around the rim of my asshole. Carol began to test the waters so to speak and began pushing one then two then three of her fingertips into my ass.
By jerking me off at the same time, I can’t say that I felt any pain. But I was confused by the pleasurable sensations coming from my butt. Soon Carol was finger fucking my asshole and could tell from my moans that I was enjoying it. The longer she did it the more my asshole relaxed and the more fingertips she could stuff inside me.
I was swooning in ecstasy and about to cum however, she tightened the grip of her right hand around the head of my cock so that I couldn’t. It was like I was in pain (blue balls) and pleasure (her fingers up my ass) at the same time. She stopped kissing me and told me she wouldn’t let me cum unless I played with her ass.
So I tried to focus on my fingertips and pushed them into the crack of her ass. At first I thought I had mistakenly reached down too far and was in her pussy. But no I was in her ass! I found out later that she loved anal sex and had alot of fingers, cocks, dildos fuck her.
I tried as best as I could to finger fuck her ass, but I was too preoccupied with what she was doing to me. Her fingers (three now) were pistoning in and out of my stretched asshole. It felt so good. I just wanted to cum!
But Carol wouldn’t let me because I was not finger-fucking her ass well enough. At one point she stopped kissing me, took her hands off of me, turned around and walked back to the beach. My cock was throbbing. I was tempted to finish myself off, but from the amount of people swimming or walking around in the water around me I couldn’t chance it. So I bent my knees and felt around my ankles for my Speedos. I pulled them up without looking too obvious. My cock was so hard that I couldn’t get the waistband over the head of my 7 inch long cock. Now what was I going to do? My asshole hurt slightly as it closed to it’s normal state.
I decided to go for a swim until I lost my erection. I hoped my swimsuit wouldn’t fall off as I swam but I simply couldn’t pull them up any higher. I swam around and eventually lost my hard-on. I walked to the towels Carol and I had spread out next to each other. There she was talking to a very tall and muscular black man.
He too wore a Speedo but it was cut much smaller than mine. It was barely large enough to contain his cock and balls. I couldn’t take my eyes off his dick; it looked enormous! When he saw me he got up and walked away I could see he was wearing a thong! I had never seen any man wear a thong at a public beach before. I was stunned.
I sat down next to Carol and asked her if she knew the black guy. She said he had been her boyfriend many years ago. I wondered why they had broken up but decided not to pursue it.
After that day Carol taught me all the basics about sex. Mainly how to please her and control myself so that I wouldn’t cum too soon. It was all pretty normal stuff. Nothing kinky.
Soon we moved in together. We lived in a small room of an old apartment building. Because it had been built so long ago the walls and floor were made of thick concrete. We literally couldn’t hear our neighbours. I assumed they couldn’t hear us either.
Carol knew of my love of nudism and supported my being nude when at home. Sometimes she would be nude too but not always. Little by little I found Carol controlling my wardrobe at home. That is to say she made it clear that she wanted me to be nude at home all the time.
Well that’s not quite true. I was allowed to wear my eyeglasses and a butt plug. Oh yes that butt plug. No sooner had I gotten used to one and Carol put in a thicker butt plug. With lots of lube I soon became comfortable wearing a butt plug. I didn’t know why Carol wanted me to wear it, but she seemed pleased at my progress.
At certain times I was so relaxed that it would fall out when we had sex! I was embarrassed by this, but Carol was proud of my anal progress. She said I was coming along nicely. Sex had changed between us. Carol was now the instigator. I was no longer allowed to be on top. I was to keep the butt plug in while she sat on my cock. The cock ring made sure that I didn’t cum until Carol wanted me to.
Being nude at home didn’t bother me until Carol started bringing her girlfriends or female colleagues from work over to our house unannounced for supper. In time I soon became comfortable with being nude all the time—even in front of strangers.
Then one day she came home with a funny look on her face. Carol was especially kind and attentive to me. For a few weeks I had been wearing the thickest of butt plugs Carol had me wear. After dinner and a bath that we shared, Carol and I went into the bedroom. She made sure to lube my asshole really well. then she pulled on a harness around her waist. I didn’t understand what she was doing until she affixed a dildo to the end of the harness. It hit me: Carol was wearing a strap on!
My cock slowly began getting hard. I was so turned on by the long thick plastic dick hanging from her crotch. The contrast between her sweet tits and cock got me very horny. She rubbed some lube on the end of the dildo as though she was a man jerking off.
Carol told me that ever since that day at the beach, she knew that my anal virginity was ripe for the picking. Carol assured me that I would love it as much as she did. I recalled the few times that I had fucked her ass, Carol had really seemed ot enjoy it.
To be continued … .
