During my college years I never really had a girlfriend. I lived with my mother which was the cheapest way to get through college. My mother’s best friend, Helen, often came over to visit. I liked Helen. She was in her early sixties and in good shape for her age, nice skin, not too many wrinkles.
She did however have the largest, saggiest tits I’ve ever seen. Helen did have one nasty habit. When my mother was not around she would ask me the most embarrassing questions.
”Do you have a girlfriend at college, Frank?”
”No Helen, I don’t.”
”A young guy like you and no girlfriend? What do you do for sex? I bet you masturbate a lot, don’t you?”
I felt really uncomfortable. At the same time, an arousing feeling swept through my body and I felt the urge to answer her honestly.
”I guess I do masturbate.”
“How often? Now be honest.”
”Every day, sometimes, two or three times a day.”
I was now hot and bothered, my cock started to rise in my gym pants. Unfortunately, Helen had a clear view of my pants and crotch and I was certain she noticed it.
”Do you get hard spontaneously or what do you do before you start jerking off?”
”I watch porn.”
”What kind do you like?”
”The usual stuff, lesbian, blowjobs, threesomes.”
”And what about a really perverted fetish?”
Now I was fully erect and Helen knew it, she kept staring at my crotch.
”Studly young guys having sex with old women,” I mumbled.
”Really, interesting.”
She got up abruptly pointing to the tent in my shorts: “If you ever need help taking care of that just stop by my place.”
With that, she left.
A few days later I was watching GILF porn again. I was about to start jerking off when Helen’s parting words popped up in my brain. I quickly pulled up my pants and texted her.
”Is this a good time to stop by?”
”Sure,” she texted back.
I ran to my car, quickly drove over and rang her doorbell.
”Come in, Frank,” Helen said opening the door.
She led me to the living room.
”I thought about what you said the other day,” I stuttered.
”What was that?”
”You said if I ever needed help with that I should stop by.”
”I see, well, for now, all I need is a good foot rub, my feet are killing me.”
”I can do that,” I replied eagerly.
Helen took off her shoes and socks, sat down on the couch, while I sat cross-legged on the floor in front of her. I started to massage her left foot.
”Oh, that feels so good,” Helen moaned.
After a while I started moving up her leg, massaging her calf muscle. I moved closer to her to get a better reach. Helen stretched out the other leg and rested her naked foot on my crotch. I became hard instantly. Helen’s foot kept rubbing my erection and tickling the tip of my cock with her toes
It was too much. With a sharp snort, I ejaculated. A big wet spot started forming on my shorts.
”Look what a mess you made on your shorts. Take them off and I’ll wash them.”
Reluctantly, I stood up. Helen unceremoniously grabbed my shorts by the waistband and pulled them down exposing my semi flaccid cock. Cum was oozing in long strings from my pee hole.
”Take off the shirt too,” she commanded.
I took off the shirt and handed it to her. She threw my shorts and shirt on the couch and sat down.
”Come over here, Frank, I need to take a closer look at you.”
I walked over. Helen started to run her hands all over my body, pinching my nipples and squeezing my butt. Within seconds I was hard again. Helen gently cupped my balls, rolling them back and forth in her hand. My cock was about to explode. Helen took a firm hold of it.
”You have a well-toned strong body, Frank, and a rock hard cock to match it. I admit I have missed that feeling.”
Helen pulled me closer, leaned forward and suddenly her soft big lips engulfed my cock. Her tongue circled my cock head followed by soft sucking. I was absolutely in heaven. I had never felt anything like this.
Helen stopped.
”You are a virgin, aren’t you?”
”Please don’t stop. Yes, I am a virgin, please don’t stop,” I pleaded.
Helen resumed slurping on my dick.
I exploded again, shooting my hot load into her mouth. Helen gagged and spat all of it on my shirt on the couch.
”You got what you came for, Frank. Please leave now, I have to get back to my work.”
She left abruptly. I quickly put on my cum stained shorts and shirt and drove back home, hoping nobody would see me before I could clean up.
I didn’t know what to make of this experience. It was my best sexual experience so far and I was looking forward to repeating it. On the other hand, I felt embarrassed about having sex with an old woman. What would my friends think? Those doubts only lasted until I was horny again and I would masturbate reliving the experience.
The following week my birthday was coming up and I fantasized about asking Helen for a “birthday gift”. I never mustered the courage.
On my birthday I received many gifts. I was going through the gift cards when I saw one bigger envelope that said “please only open in private.” My interest piqued. I ran into my bedroom, closed the door and ripped open the envelope. It was from Helen. I pulled out a DVD. Granny Norma loves young studs, the title read. I then pulled out a card and opened it. It read:
