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First Date

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First Date by Jason Matthews

On our first date, I went to Joy’s grandmother’s house in Hewitt where she lived temporarily at the time. I took her to a Bible study at a friend’s house. On the way there, she appeared to be dressed normally with a long sweater over her blouse and pleated skirt. She sat on her side of the car and conversation was normal first date, get acquainted stuff.

But as soon as we got in the car for the return trip, she started “turning on” to me sexually. She was like a totally different person. Our conversation became intimate, even embarrassing for most couples on a first date. But I was not easily shocked and neither was Joy. She kept probing deeper into my first marriage, especially on the subject of sex.

She removed her sweater in the darkness and it quickly became obvious that she was wearing a very low cut blouse and short pleated skirt which carelessly appeared to remain high on her legs as I drove. I noticed her silently unbutton her blouse in front as I drove. She moved over close to me and grabbed my right hand, placing it onto her breasts for me to fondle.

I was stunned but obliged her by groping her breasts for several minutes.

Knowing her agenda even though I did not, she grabbed my hand a second time. Joy moved my hand down under her skirt to her pussy, placing my hand on her already wet labia which I took the hint and started caressing, still utterly shocked by her quick sexual aggression. Not satisfied with my caressing her pussy folds, she pushed two of my fingers up inside her body. Driving was becoming more difficult as I then finger-fucked her.

Finally I returned with her to the house around 9pm. After I parked in her grandmother’s driveway, we continued to talk. She was already next to me on the bench seat of the large Cadillac sedan and put her hands on my face and upper body in a friendly fashion as we talked. She had already made it obvious that she was seriously attracted to me.

The conversation quickly focused on our past sexual experiences which she appeared anxious to discuss as she continued to want me to finger fuck her pussy. She wanted to know everything about my past sexually. I thought that not unusual since each of us had been previously married for a number of years and were not shy about the subject.

As we talked, Joy casually unfastened all the buttons on my shirt and slipped her hand inside. She lovingly caressed my chest and upper body muscles with my fingers still probing her pussy. That got me really excited about her. By that time, my erection was huge inside my trousers.

Joy appeared to ONLY want to talk about our sex, and quickly I realized that we would definitely have sex even on this first date. She asked a lot of questions about sex with my first wife, especially what we did in foreplay and then to cause each other to orgasm. We assured each other that we were clean of diseases.

She asked if I was able to get a woman pregnant. I said “yes”, and explained that my first wife had a miscarriage. Then Joy said that she did not like condoms, that sex was better without them. Then she told me that she was on birth control pills. After a lot of talk about sex and her caressing hand all over me, she whispered that she was not wearing a bra or panties tonight. I had already suspected that she was not wearing a bra, but the lack of panties surprised me.

She said that she wanted us to fuck in the car. Her long sweater had kept her not wearing underwear a secret. However, her short pleated skirt had revealed a lot of leg and got my attention when she removed her sweater before getting into the car for the trip back. I had noticed that I could see an incredible amount of breast and leg in the front seat of my car. Her short pleated skirt had been teasingly and carelessly high around her upper legs on the return trip.

As we sat in the car next to each other, Joy leaned close and wanted to kiss. Her kiss was anything but casual; it was what I call a “fuck me kiss”. Her kiss was incredibly aggressive and erotic. It was an intense French kiss with her doing heavy tongue and mouth interaction. It was a kiss like “I am horny as hell and ready to be fucked.”

During that kiss, she removed her hand from inside my shirt and dropped it abruptly onto the crotch of my trousers. I jerked with surprise as she firmly grabbed my penis. Joy started boldly groping my genitals and feeling the size of my penis and testicles on top of my trousers. She groaned her approval in the kiss as her fingers moved back and forth along my already rigid penis and testicles. My genitals have always been rather large.

When the kiss ended, she asked me in a sexy voice if she could suck me off right now in the car. She already had me so horny and worked up that my erection was straining to fit inside my trousers.

“Oh fuck yes, Baby!” I uttered with her hand still anxiously groping my genitals inside my clothing, shocked but pleased by her sexual aggression on our first date.

Like a professional and in apparent preparation to do that, she leaned back and unbuttoned the front of her blouse all the way down. I took that as a sign that she wanted me to fondle her breasts during oral sex. Then she pulled her blouse out of her skirt to fully expose her breasts. They looked nice, but were simply average for a petite woman like her.

Without a word said, she leaned down and used both hands to unzip my trousers. To assist her, I moved the seat all the way back and tilted it backwards to give her more room behind the steering wheel. It was obvious by the way she unzipped me that she had done that many times before. Joy pulled my genitals out of my underwear and started handling my balls and penis in an anxious manner, continuing to feel me all over.

Joy quickly bent her head down into my lap. As soon as she went down on my penis with her mouth, I shoved one hand down under her to get a handful of breast as I knew she obviously expected by unbuttoning and opening it. I kept fondling her while she viciously mouthed my penis and groped my testicles. By that time it was still only 9:30pm in the driveway of her grandmother’s house.

She handled my genitals expertly and moved her mouth rapidly up and down on my penis as if she was in a hurry. I was stunned and pleased that she was giving me oral sex on our first date. She was doing a fantastic job of it.

After a few minutes, my rigid penis felt something I had never felt before. I knew that my penis was literally going into her throat and the feeling was incredible. In disbelief, I looked down to see her lips kissing my testicles on each downward motion, which meant that my 8 inch cock was completely inside her mouth and throat. I never dated a woman able to do that, and she was expertly not gagging as she continued to deep throat me. I knew that I would come soon and probably literally inside her throat, not just her mouth. Mentally, I was in literal heaven as she continued to deep throat me.

Later she admitted that giving a guy oral sex was always her favorite thing to do as foreplay for sex. I could tell that she really enjoyed doing it. At the time it seemed to be more for her benefit than mine except that she expected me to fuck her afterward.

Both of us had been married for years and of course used to having regular sex. I realized later that Joy wanted to determine if I would be a good sex partner and therefore suitable for marriage. She continued to savagely go down on my penis until I came inside her throat about ten or fifteen minutes later, writhing in pleasure on the front seat of my car. As my dick squirted semen it felt so wonderful being inside her throat. It was obvious that my moaning and groaning thrilled her. That was the best oral sex I had EVER had. Joy later told me that she prided herself at being good at it, and that she would always suck me off before intercourse mainly because she simply wanted to do it.

Not having had sex in awhile, I came volumes inside her throat. She expertly consumed all my semen and cleaned me with her mouth and tongue. I was stunned. I had never even come in my first wife’s mouth, and never been deep-throated by ANY woman I dated.

Joy sat back upright on her side of the car. It took a minute or two for me to recover. She left my trousers wide open and my genitals exposed. She also left her blouse open and her breasts visible. Joy sat quietly in the darkness, patiently waiting for me to respond. She wanted to see if I had a desire for intercourse after her giving me oral sex. I had made enough noise to let her know that I really enjoyed her efforts and already thanked her for cleaning the mess with her mouth. She was purposefully waiting to see what I would do next. She hoped that I would want intercourse as a way to thank her, but more importantly, to determine my sexual appetite.

Now savagely excited, I turned to her and placed one hand on her breasts again, grabbing them and moving from one breast to the other. I took my other hand and moved it under her skirt, wondering if she would resist. She did not. She made no move to stop me, and her movements even encouraged me. I was accustomed to there being some resistance to sex on a first date with other women, but just the opposite was true with Joy….. she expected it. I soon discovered that she was wet and verified that she was not wearing panties. I took that as a sign that she expected intercourse even before I picked her up for the date. I started caressing her labia, then slipped first one and then two fingers inside her vagina. She leaned back and made sounds indicating that she was enjoying that.

After finger fucking her for a few minutes with her full acceptance, I decided that it was too risky to do much more in the car in her grandmother’s driveway. I told her that. Her response shocked me.

“Look, Roger,” Joy informed me in a serious tone of voice, “I wore this short skirt and no underwear tonight so we could easily fuck, even in the front seat of this car. I expect you to fuck me before the date is over.”

Without saying a word, I scooted over to her side of the car. She raised herself above the seat towards the windshield to let me slide underneath. She also raised her skirt around her waist, and then I guided her down on top of my penis. Joy was so wet that I easily slipped inside her pussy when she sat down on top of me. Then she started moved up and down on my penis.

I then realized that my words had pissed her off because her tone continued serious. Joy went on to inform me that she needed to know that I would be a good sex partner for us to continue dating.

She said bluntly, “We have to fuck tonight or we don’t need to date!” In a softer tone, she explained that I needed to prove myself as a guy who could give her a good orgasm. She said that she could not be married to a guy who could not do that. (We had not even talked about marriage on our first date of course.) She said that I needed to find a place to fuck her now. She said “go park somewhere else, take me to your house, or take me to a motel, I don’t care, I just need to be fucked right now or I will go nuts! I’m telling you, Roger, take me somewhere and fuck me but I better have a good orgasm! Or else our dating is over!” Then she explained that she wanted rough sex to see my limits.

She said and I paraphrase, “I need you to take me to your house and r*pe my pussy so I can decide if we should continue dating. If you cannot fuck me after I sucked your dick and letting you come inside my mouth, I need to know that. I cannot tell you how important great sex is to me. Take me to your house and savagely fuck me like a rag doll or we won’t keep dating. I have to know if you are a good sex partner and if you crave my body. If you cannot please me, then I don’t want to spend any more time dating you!”

Joy leaned back in the seat on her side of the car like she was in agony for an orgasm. She pulled a dildo out of her purse, pulled her skirt up around her waist and started shoving it in and out of her pussy as I watched. I had never seen a woman so in need of sex. As I backed out of the driveway, she was still fucking herself with the dildo on her side of the front seat with her eyes closed and making sexual sounds of pleasure.

That was the first of many times in the future where she would utter words similar to that during our marriage, each time demanding that I make more of an effort to please her sexually. Years later she would suggest “open marriage” so that she could be satisfied sexually in ways which I continued to fail to please her. I have always lived with the fear that she would find sexual pleasure with or without me, especially if I failed to fuck her hard enough or often enough.

Stunned at her saying that and not ready to lose her, I started the car and backed out of the driveway. I headed in the direction of my house. Yes I wanted sex, just not in that location in the driveway. I was already separated from my wife and she had already moved out months earlier, so I had the house to myself and Joy knew that.

On the way to my house, Joy stop using the dildo and went back to handling my genitals, but now she handled my penis only to see if I could get another erection. At my much younger age and her skilled hands, fortunately I was able to become rigid again before we arrived at my house. It was obvious that she was pleased at my virility.

As we left the car and approached my front door, we both had hands on each other in an erotic manner. Once inside, we proceeded to undress each other and make our way to the master bedroom. I stopped at the couch in the den and bent her forward over the couch, anxious to get my rigid cock inside her. She complied and bent forward over the couch. I pumped her doggy-style five or ten minutes over the back of the couch. Not wanting to cum that way, I stopped and moved her down the hallway to the bedroom.

By that time she was virtually naked as was I, and we fucked for several hours.

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