This story continues where Older is Better leaves off. Sally, a 60 year woman who works in a sex toy store, is teaching Marco, a college student, the ins and outs of sex. Per their agreement, after Marco had secured a date at school, Sally is ready to take his cherry for his own good.
Older Gets Even Better
It was my day off, and at six o’clock I was sitting up in bed reading a trashy novel when Marco called me. I had wondered how he was doing after his first lesson in the art of love. When he had walked into Fantasy Land, the sex shop where I was working, I could tell he was nervous and inexperienced. As an older woman with a high sex drive, I took it onto myself to teach him how to approach a woman, and how to properly pleasure her. At my apartment he had done well for a virgin. After some instruction in basic interactions between men and women, I had jerked him off, then let him finger me to an explosive orgasm. His calling meant that he had overcome his shyness and was going on a date with someone from school.
“Marco, nice to hear from you. I take it you have good news?”
“Saturday I’m going on a date with Tina from my chem class. Sally, I don’t know how to thank you for helping me out the way you did. You said you would teach me some more; did you mean it?”
“I’m very happy for you, and of course I meant it. Can you come to my apartment tomorrow at 7:00?”
“I’ll be there. Last time before I came I, you know, jerked off? Do you want me to do that again?”
“Absolutely. Now, give yourself plenty of time and take notice of when you start masturbating. I want you to think about me, the way I looked spread eagle on the bed. I’m naked and you can see right up my cunt as I play with it. Work your dick slowly and pay attention to how aroused you are. If you are getting too close to the edge, let go, relax, and count to 20. Try to think of something besides sex, the object is to prolong the session as much as possible. When you do cum, check the clock. I want to know how long you lasted. And before you come over, pick up some condoms. Nothing fancy, just the regular lubricated ones.”
“Okay Sally, I’ll do just as you said. I’ll be there at 7:00.”
After I hung up, I tried to read but memories of Marco kept distracting me. Maybe it was the change in his attitude I saw when he left, his shoulders were up, and his stride had a purpose. Or maybe it was his cock. Not the biggest I have had, but one of the most beautiful. The shaft was the color of coffee with a splash of cream, strong veins and a bit of an upward curve. A reddish glans, when not covered by his foreskin, flared wide at the base and had a perfect helmet shape. Almost of its own accord, my free hand crept into my panties and lazily stroked my outer lips. The novel lost its interest as sexual desire took over. My hand pushed further into my panties as I remembered that first visit. I imitated the way he had probed me, fingers pushing against my cunt walls and tugging gently at my labia before pushing deep into my vagina. Giving up on the book, I stripped down and got comfortable with a towel under my ass. As I had gotten older, I found my orgasms tended to be quite wet, very pleasurable, but a bit messy. I had relished the feel of his foreskin as I slid it back and forth in his precum, and the weight of his balls as I rolled them around in their loose sack. The shaft had quivered in my grasp as I pumped it, his back arched as he exploded. It was a shame that he had come so quickly, but I really couldn’t expect too much, could I? No matter how many times I’ve seen it, sperm shooting out of a cock always fascinates me. I especially like when it’s thick and lands on my tits, I massage it into my nipples and mix it into the sweat. By now, I was deep into fantasizing about Marco and how his cock will feel as it slides into me. Juice was running freely down my crack, my fingers so wet I knew if I wanted, I could penetrate my bum easily. I was too far into my fantasy to enjoy some butt play, a need for immediate release took me. From the bedside table I grabbed an electric toothbrush. The firm bristles danced on my clit as I pumped three fingers into my heat. My orgasm built power, starting with slight spasms that caused spurts of pee that mingled with my other juices. I sucked the mixture off my fingers and squeezed my thighs together, trapping the brushes hard on my love button as I felt the orgasm crest, wave after wave of pleasure washing over me.
After a quick clean up I drifted off to sleep, thoughts of sweet sex filling my dreams.
I was glad the shop was fairly busy the next day, keeping my mind off the excitement planned for that evening. One of my regulars, Kim, could tell from my grin I had something going on. She’s a real cutie, a bit younger than me, and loves to talk about her sexual shenanigans. On slow afternoons I sometimes asked her to stop by just to chat. It was usually a competition between us to see who could tell the raunchiest story. Last time she told me of taking home two guys, they started out having sex in the basement and finished in the attic, where as Kim put it: “Between the heat up there and the two cocks l was practically swimming in sweat.” I told her about Marco and promised a complete report as soon as possible.
Home at last, I just had time to shower, dress, take care of my hair and apply a little makeup. Instead of the conservative clothing of our first encounter, I went with a lacy thong and a push up bra that left my nipples exposed, breasts sticking out as if offered on a tray. Sometimes, a girl just wants to feel like a slut.
Opening the door, I was very pleased by what I saw. Marco had updated his wardrobe to go with his new hair style, a floral shirt topped jeans that hugged his ass and showed off his package.
After getting settled on the couch with glasses of wine, I asked for a complete update on his dating situation.
“I did as you told me and stopped trying to get a date and talked about class stuff instead. Tina is really good at chem, and when I asked her, she agreed to give me some help. We spent an hour or so in the library studying, then I invited her for coffee. We did that for two days, and when I asked her to dinner she said yes. I even got a kiss when we said goodbye.”
“Excellent news Marco. Now, tell me how you did this afternoon with the task I gave you, and I want all the details. Talking can be a form of foreplay. Use the dirtiest words you can, and be brutally honest with me. If I don’t get excited as you’re talking, you’re not doing it right.”
Marco took a swig of wine and began: “At five I started getting ready to jerk off, slowly taking off my clothes and imagining you were doing the same. Once I was naked, I lay on the bed with my head propped up so I had a good view of my cock. I figured you’d start slowly by playing with your tits, so I started rubbing mine. I didn’t realize how sensitive my nipples were until I started really pinching them, they got hard, and it turned me on. When your nipples were big and red, you moved your hands down and played with your cunt. I started stroking my dick and imagining you rubbing yourself and getting slick juices over your fingers and licking them. You opened your legs wider and pulled your knees up until I could see all of your open slit. I imitated what I saw in my head, pulling my legs up and reaching around to play with my balls. It didn’t take long before I had to let go of my dick and calm down for a bit. The whole time, precum was leaking out and made a pool on my belly. When I started jerking off again, I scooped it up and covered my cock with it. I used a real light grip on it so my hand slid easily up and down. I saw your fingers start sliding in and out of both your pussy and butt, and used more precum to wet my asshole and pushed a finger all the way in. It felt real good moving around, and I even wondered if I had anything bigger like a candle I could use. I kept stroking and fingering, when I finally came, I had stopped six times and it was 19 minutes past the hour.”
By the time he was done talking I was so hot my panties practically dripped, and he had an uncomfortable looking bulge and a big wet spot in his pants. Taking him by the hand, I led him to the bedroom and explained to him that we would start the next lesson without any more foreplay as we were both already excited. I was anxious to see how long he could last inside me after all that build up. Naked, I put him on his back so I could control the pace and after pulling back his foreskin and stroking his beautiful shaft a few times, slid a condom over his cock. My eyes locked on his, I straddled him, and lowered myself onto his dick until his pubic hair was against my naked mound. His manhood inside me added its heat to my fire, after relishing the sensation of being filled for a minute I started rocking back and forth and talking to him.
“A lot of women like this position so they can control the action. It’s very intimate when the position lets you look into each other’s eyes, and obviously, like this her tits are available. Now, if you get close to cumming tell me and I’ll stop moving for a bit. Women may take a while to cum, but they also don’t want to just fuck for hours. A pussy is muscle, and muscles get sore. If you get to where you’ve been in her for half an hour, she’s probably ready for you to stop and give her a rest.”
That said, I leaned into his chest and started moving slowly up and down on his cock. I would have liked to grind my mound against him so my clit got some love, but didn’t want to overstimulate him yet. He did well for his first fuck, telling me to stop three times before his body stiffened and I felt him shoot his load.
“That was good for your first time, you lasted about six minutes I think.” Rolling off I gave him a box of tissues and told him to carefully remove the used condom.
“Condoms go in the trash, not the toilet, understood? Now it’s my turn to cum, get back on the bed.” When he was set, I lowered my cunt until it was a few inches from his mouth. “Not all guys like this because it can be smothering, but women really get into it. You’ll have almost no control, by moving we decide where your tongue can reach. If we plant our asshole on your mouth, it means we’d like for you to lick it, and if you just shot a load in either hole and it’s dripping out, be a man and clean it up, it won’t kill you."
Lowering myself the last few inches, I sealed my cunt against his lips. His tongue lapped at me slowly at first as he got accustomed to the taste.
“Make love to the entire area, not just the vagina and clit. Now my labia are fairly long, you can suck the ends of them right into your mouth, it feels great. Nibble here and there but don’t bite. And you can use your nose, it’s hard enough to stimulate the clit, and you can even penetrate her with it.’
Rocking back and forth, I used his mouth on all my parts, moving back he could tongue my button, moving forward his nose raked against me until my vagina engulfed it and he found his tongue pushed against my asshole. What he lacked in skill, he made up for in enthusiasm. When I was ready to cum, I got his tongue back so he could work on my clit. Even without a splash of urine I get very wet, while my orgasm wasn’t earth shattering, I still left his face a sticky mess. I asked him how he felt about doing that.
“I enjoyed doing that for you, it seemed strange at first, maybe because in my country women are expected to be subservient, and you were very dominant. And I wasn’t sure about licking your ass, I thought it would taste real bad, but it didn’t. And I was happy I made you orgasm, that was very important to me.”
“You did fine for your first time. You will learn to pick up on what is pleasing her and what she finds annoying, and trust me, there will be things she doesn’t like. Remember, talking is important, especially at the beginning of a relationship. It can be embarrassing, but it pays great dividends. Up to now I’ve called all the shots because there I things I wanted you to learn. Now it’s your turn. What would you like to do? If you have some fantasy, now you can make it happen. There is nothing you can think of that is going to shock me.”
Marco had a hard time getting the words out. “Sally, there are many things I have seen that I would like to do someday, but now, I’d like to know what a blow job feels like, and I would like to make love to you from behind so I can see your butt and put my finger in it.”
“That sounds like a wonderful way to end this lesson. Stand by the bed and I’ll get on my knees for you. You can guide my head with your hands but don’t force it, some women like being used like that but most don’t.”
Really, I love the sight of a cock and balls when I’m on my knees. Inches away, all the features and imperfections are in widescreen, hi-definition technicolor. I quickly took all of Marco into my mouth while he was still semi-soft so I could roll his glans around under my tongue and squeeze the shaft. He quickly stiffened in my mouth, and I released him to examine his balls. I love playing with a guy’s sack. You can stretch it out until the wrinkles disappear, you can suck it into your mouth, or play with the balls like a cat making them swing back and forth. Moving back up I took his ass in both hands and worked my way down his now rock-hard dick until my nose pressed into his belly. As my mouth was filled with his meat, my nose was filled with the smell of his excitement and sweat. With suction and tongue, I made love to his member for a few minutes before reluctantly releasing him so we could fuck. I turned and knelt on the bed, presenting my ass for his inspection. Head down, I reached back and pulled at my cheeks, offering my innermost parts for his pleasure.
“After you put on the condom, in the table drawer there’s a tube of lubricant, squirt a little on my asshole. Anytime you do anything anal, lube is a good idea.”
After the first fuck and the oral I was very relaxed, with eyes closed I enjoyed the feel of his finger as he caressed lubricant into my backside, followed just a few seconds later by the of his dick pushing against and then entering my cunt. I know he was enjoying the view as much as I enjoyed the penetration, I wiggled my ass inviting his finger to enter. One finger buried in me was nice, but I was in a mood and asked for a second. Comfortably stretched I leaned into him as he began stroking. I could feel his fingertips against the membrane separating my holes and knew he was experiencing the feel of his cock as it slid in and out. He twice brought me to orgasm, any sort of double penetration always gets to me. Each time I came a squeezed my sphincter down on his fingers as hard as I could and trapped them, with the second orgasm my bladder finally gave way, piss rolled off his dick and down my legs. As an older woman, I’ve learned to expect this, and a rubber sheet is always on my bed.
Using the stop and go technique he managed to last a bit longer than the first time, before he came he grabbed me by the waist and got in three hard, cock burying, hip slapping thrusts before collapsing spent.
After a bit of a rest I got him dressed and pushed him to the door.
“You’re a good kid Marco, I think you’ll always treat women with the respect they deserve. After your date with Tina call me and let me know how it went. We’ve covered the basics, but maybe you’d like to try some of the more interesting activities I know.
If I write a third part to this, Marco is going to find out that Sally is one kinky woman.