The Adventures of G Ch. 03

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She helps a boy become a man.
2.9k words
4.58
63.7k
10

Part 3 of the 11 part series

Updated 10/29/2022
Created 09/16/2007
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I had just returned from a trip and was getting ready to go out again when my partner called me into his office and told me we had landed a major contract in New York, it would take 6 months and the client wanted me to manage the project on site. The bad news was that I would have to move there for the duration of the project. Actually, I was excited at the prospect of moving to New York for 6 months.

As soon as I got back to my office I called Gwen, my best friend who lives in New York to tell her the good news.

"Oh Honey," she said, "That's great except I have bad news. I have to go to Europe for three months on a fashion shoot and tour. But I have a great idea. Instead of staying in a hotel, stay at my apartment. I have a huge extra bedroom you can use. Mrs. Abernathy, my maid comes in 6 days a week to clean up and cook so it'll be just like living in a hotel but with all the comforts of home."

"That's tempting," I told her, "but won't it be a bother to keep Mrs. Abernathy just for me?"

"There is one tiny hitch," she said, "my son Johnny is still at home."

"Didn't he start college this fall?"

"Actually he graduated high school at 15 is now a college junior at 18, studying business. I didn't want him moving away so young so he goes to college in the city. He's very bright but extremely shy. He won't be a bother and I would really sleep better knowing someone would be staying with him while I'm away."

"OK," I agreed, not really knowing what I was letting myself into.

A week later I was in New York, knocking on Gwen's door. She gave me a big hug, introduced me to Jonny who could barely look me in the eye and gave me the tour. It was a beautiful, spacious apartment. She saved my room for last. It was gorgeous, a huge queen size bed, a French Provincial desk with a computer, a bath with a whirlpool tub and a huge walk in closet.

It was like living in a hotel. The only time I saw Johnny was at dinner. When he learned what I did for a living, he asked if I would help him with assignments if he needed help. He was very bright and the problems he brought me were always complex challenges and I enjoyed the challenge.

I was enjoying living in the city. I loved the work and the nightlife.

I was out one Saturday evening, attending a corporate event and it was late when I got home. I quietly opened the door and let myself in. The apartment was dark and silent. I tip toed down the corridor to my room when I noticed a light shining from Gwen's door. I peeked in, expecting to see Gwen home for the weekend. What I saw shocked me!

The drawers of her dresser were pulled open. Bras, panties, stockings, slips, chemises, satin PJs, garter belts, and baby dolls of every color and style were scattered everywhere. Standing in the middle, wearing a satin robe was Johnny. He had a red satin bra in one hand, holding it to his chest and a pair of matching panties in the other. Sticking out of the robe was a huge, hard gorgeous cock. I couldn't believe my eyes as I took it all in. Suddenly he took the bra, wrapped it around his cock and began to slide it between the satin cups. The look on his face was ecstasy as he pumped slowly then faster and faster. The sight of that cock pumping in and out of that red satin bra started to really turn me on and I felt myself getting wet. He pumped and pumped until he stiffened and finally came, catching streams of cum with the panties until he was drained, then collapsing on the bed.

I didn't know what to do. I quietly stepped back toward my room when a heel accidently clicked on the floor. I quickly tip toed to my room, went in and closed the door. The sight of that cock, pumping in and out of that red bra had really turned me on. As I walked to my bed, I unzipped my dress and walked out of it. I reached into my drawer, pulled out my two favorite toys; a small vibrator that drives my clit crazy and a 7 inch vibrating dildo that drives my pussy crazy, my magic wands. I lay out on the bed, pulled my panties aside and spread my legs. I licked the small vibrator, turned it on and started to massage my clit. The sensations of pleasure were indescribable as I swirled it around and around. I could feel an orgasm building but I needed more. I took the vibrating dildo, turned it on and gently inserted it in my wet pussy lips as I continued to massage my clit. I pushed in slowly, inch by inch feeling it fill me and feeling the sensations of it vibrating. I started to pump, in and out faster and faster, harder and harder, massaging my clit. Faster and faster, around and around, the sensations electrifying every pore in my body when I started to shudder and shudder, experiencing an earth moving orgasm.

I lay on the bed, still in my bra, panties, stocking, garter belt and heels and as I tried to catch my breath I wondered how I was going to handle what I saw. I knew Johnny was extremely shy and lacked self confidence. I didn't want to embarrass him but on the other hand he had a lot of issues that needed attention. I got up, pulled on a robe and marched down the hall and knocked on his door.

"Come in" he stammered quietly.

He was sitting on his bed, dressed in shorts and a t shirt. I sat down beside him. He was quiet, very embarrassed and wouldn't look at me.

"I guess you saw me in Mom's room when you got home." He whispered.

"Do you want to talk about it?"

"Not Really"

"I really want to help you." I told him, "Help me understand. I won't tell your Mom."

I touched his arm gently and slowly and painfully the story came out.

When he was younger he discovered some of his mother's lingerie in the laundry hamper. He took it out. It was soft and smooth or lacy and it made him feel horny. He would try things on. His "thing" would get hard. When he massaged his "thing", it felt so good that he never wanted it to end. He would massage and rub until he came. Whenever he was frustrated, he would go to the laundry bin. He found the smell of the lingerie different but it always made him feel horny. He told me when his mother was away, he would go to her room, open her lingerie drawers and try on different things to make him horny and then he would rub himself until he came. He would wear lingerie in the house and even sleep in it because it felt so good. He found solace and comfort in his mother's lingerie.

He finished high school at a very young age, went to college and never had any friends his own age. The girls in school were always older that he was. They wanted "Johnny's" help in school but they thought him a smart little brother. He never went to his prom, never been on a date and had ever even kissed a girl.

As we were talking, he kept his eyes down. I noticed he was glancing at me. His eyes kept going from me breasts to my legs to my heels and back.

"Would you help teach me to have confidence around girls?" He stammered.

My heart went out to him.

"I'll help you," I said, "but you need to trust me and follow my lead."

"I'll do whatever you ask." He replied.

I moved toward him and gently kissed him on the lips. He pulled away surprised and licked his lips.

"What's that on your lips?" He asked, "I love the taste."

"You've never tasted lipstick before, have you?" I asked. He shook his head no.

I moved closer, put my arms around his head, pulled him toward me and kissed him again. He responded and awkwardly put his arms around me, not really knowing where to put them. I forced my tongue in his mouth. He did the same to me. Our tongues darted around in our mouth and soon we were deep French kissing.

The thought of his young cock, that had never been kissed, sucked or in a pussy and that I was going to be the first, was really turning me on. He was starting to squirm. I dropped one arm down, caressed his chest, moved down and felt a huge hard on. I gently caressed his cock. He moaned with pleasure.

"Do you like it when I do this?" I asked.

"Yes, yes, please don't stop." He begged.

"Would you like me to teach you how to make love to a woman?" I whispered.

"Yes, yes. Please yes." He stammered.

"Would you like to touch my breasts?" I whispered, "I love to have my breasts caressed. I'll guide you" I took his hand and placed it on my breast. He held it there perfectly still.

"You can gently squeeze them and massage them." I said as I started to kiss him again. I felt his hands start to caress me as his tongue started to dart in and out of my mouth. He fondled me, his hands gliding over the smooth satin of my robe, exploring my breasts from one to the other. He slipped his hand inside my robe, gliding it over my bra, moving, caressing, then finding the gentle swell of flesh above the cups, he tried to slip his hand into the cup.

"Would you like me to take my bra off?" I said as I broke off the kiss and pulled back, untying the belt of my robe and shrugging it off. His eyes almost popped out of his head as he watched it slide off my shoulders, exposing my push up bra, breasts swelling out, nipples barely covered. I reached for the clasp, about to unfasten it when I saw the look in his eyes. I reached out to his hands, gently guided them to the clasp and showed him how to open it.

He unfastened the clasp, moved the cups to the side and released my breasts from their satin cocoon. He gently took one on each hand, fondling them. I felt my nipples start to harden.

"You can kiss them, suck them, and caress them with your tongue round and round. See how they react when you do that." I said.

He looked in amazement as my nipples grew longer and harder. He knelt between my legs, put his head down and lost himself in my breasts. He kissed one, then the other. He sucked on a nipple, swirling his tongue. I felt it grow harder as he continued to tease it, sucking, kissing and caressing while rubbing his cock on my leg.

All this breast attention was really turning me on. After what seemed an eternity, I pulled his mouth away. He was so excited. I could have let him play with them all night and he would have been happy. I wanted his first time to be special.

"Let me get undressed," I said "and we can continue on the bed."

I stood up and my robe fell. I still had on my bra so I dropped my shoulders and let it fall to the floor. He looked up and saw me, dressed only in my garter belt, stockings, panties and heels, breasts free of my bra, nipples hard, still wet and shiny from his sucking and kissing. I started to unclasp my garters when he stammered

"Please, please could you leave your lingerie on?"

I smiled at him.

"Of course I will," as I lay on the bed, "come here beside me and kiss me."

He lay beside me and we started to kiss. His tongue darted in and out of my mouth as his hands continued to explore my breasts. I reached down and traced the outline of his cock on his shorts with my finger. I started to stroke it gently and slowly. Johnny started to moan and groan.

"Johnny, would like to play with my pussy?" I asked as I moved one of his hands from my breast to my panties.

His hand was very still. He could feel the dampness from my juices that had soaked my panties. He started to move his hand around, feeling the outline of my pussy lips, moving them up and down.

"Do you feel how wet I am?" I asked, "When a woman is wet, that means she is almost ready. I need a little more stimulation."

Taking his hand, I slipped it into my panties. I guided him along my pussy to my clit and showed him how to stimulate me. As he continued to play with my clit, I pulled my hand away, slipped it in his shorts and began to stroke his cock. We were both in ecstasy as we continued to pleasure each other.

"Oh God!" He gasped, "Nothing has ever felt this good."

"Let's get rid of these." I said as I pulled my hand out of his shorts, grabbed them and pulled them off. His young virgin cock sprang out, standing at attention. I moved around, draping my nylon clad legs over his chest, heels near his face. He started to kiss and caress my legs and feet and heels.

I took his cock and put the head in my mouth. I swirled my tongue over the head and then took him deep in my mouth. I pulled back to the head, swirled my tongue then eased it out and ran my lips down the underside. Then back to the head, into my mouth, a swirl the deep in my mouth over and over and over. Finally I was concentrated on the head, swirling over and over, when I tasted pre cum. It was his first time. I didn't want him cuming in my mouth, I wanted him in me. I pulled him from my mouth.

"Please, please keep going." He begged.

"Johnny, please, I want you to eat my pussy."

His eyes widened. I spread my legs and guided his head to my wet panty clad pussy. He started to kiss my pussy through my panties, nudging my clit with his nose.

"Pull off my panties,"

He moved around, I lifted my butt and he slipped my panties off. I spread my legs, pulled his head to my pussy and draped my legs on his back. He started to kiss over and over.

"Johnny, use your tongue, go up and down my pussy lips."

He started to lick my pussy, up and down. I reached down and spread them wide, exposing my clit.

"Johnny, swirl your tongue on my clit, around and around then go up and down then...."

I couldn't talk as the waves of pleasure washed over me as Johnny ate my pussy. His tongue swirled my clit, explored my lips and returned again and again to my clit, the pleasure building and building. I pulled his head away, looked him in the eyes and said,

"Johnny, make love to me. I want you inside me."

He moved up, his cock erect. I took it and guided it to my pussy. I inserted the head in my pussy lips and gently ran it between them over and over. I guided it to my clit and massaged it with the underside of his cock. I guided it along my pussy and then, took him deep inside me.

The feeling of his cock filling me almost made me cum. The look on his face was one of pure ecstasy. I pulled my hips back, feeling him move out of me, then thrusting, driving him deep, filling my pussy. The wave of pleasure was incredible. He started to pump, each thrust filling me and raising the heights of pleasure, faster and faster, orgasm building, wave and wave of pleasure almost cresting. I wanted us to go together for his first time. I held back, the mounting pleasure almost painful, his cock filling me over and over. Suddenly he stiffened and I felt him cum deep inside me and let myself go, an orgasm washing over me as he continued to cum over and over inside me.

He collapsed on me, totally spent. I held him in my arms as he nuzzled my breasts.

"That was the most incredible experience of my life," he said simply, "thank you."

"Johnny," I said "you don't need to thank me. I think all you needed was a little self confidence. Now, little Johnny has grown up. Tonight, for the first time, you made love with a woman. I'm happy that was me, Jonathon, that I was the first to fondle your cock, to suck it. There are many ways to make love to a woman. I'm happy my pussy was the first one your cock made love to. I'll teach you many ways to make love while I'm here. We have all the time in the world."

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9 Comments
chytownchytownover 1 year ago

*****What a set-up lucky bastard!! Thanks for sharing.

RichardDastardRichardDastardalmost 3 years ago

Awesome awakening of a young man, I too was fortunate enough to learn from an older woman and can't recommend it enough !!!!

shoeslayershoeslayerabout 6 years ago
GR8 story !

Hello Garterbelt, Thanks very much for a great read.

It is always refreshing to hear how a lady who enjoys

sex is able to help a young guy be 'more of a guy'

knowing how to please a woman, in all the different

ways.

I bet Johnny felt a lot better about himself after that evening !

JhMcKnJhMcKnover 10 years ago
First Time

How incredibly great that she realized his need and took him through the preliminaries of making lover until finally letting him blow his nuts off inside her as she guided him through the process. I'm sure there will be moe\re.

shoeslayershoeslayerabout 12 years ago
That was SO GOOD an HOT

Oh yes that was a damn good read.

SO GOOD an HOT Johnny will look at

life in a whole new way now! I get the

idea she was possibly ten years older

than him, which will hopefully get him

hitched on older ladies.

Thanks so much for a great story!

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