Ryan's Story

Ryan's Story

Note: When I started this series, I thought maybe it would be ten chapters. But I keep thinking of things for Ryan to experience. I'm not sure it will end. Is there anything you'd like to see Ryan get into? Do I keep adding chapters (most are short) or start a completely new series? No end in sight.

Chapter 28

I woke in the morning with the sun coming in the windows. Mother was already gone, I was alone. Yawning, I climbed out of bed and headed for the bathroom. After a quick shower, I pulled on a pair of shorts and headed downstairs to the kitchen.

I saw the car of neighbor Gladys in her driveway next door, she must have gotten home last night. I stood in the doorway, watching.

As I stood in the doorway, Gladys came out of her house and walked to her car. As she opened the door, she saw me standing there. She smiled and walked over to our house. Pushing me back into the kitchen, she said, "Glad to see you back from your reunion. I've got a meeting to go to, so don't have much time."

She turned me around, pushed my shorts down, and bent me over the kitchen counter. As she unfastened her slacks, seeing my red ass, she said, "Looks like your mother had fun last night. I can't wait to spend an evening doing the same." Then she pushed the head of her cock into me. "But now," she said, "I only have time for a quick one." and rammed her cock all the way into me, causing me to scream out.

"Oh yeah, bitch," she said, "Scream for me. I love to hear you scream," and slammed hard into me again.

I cried out and shot my load onto the side of the kitchen counter. Slapping my ass as she fucked me, Gladys said, "It's been a few days since I've fucked a boy. This is going to be a big load." And shoving deep into me, she gave me that big load.

Sliding her spent cock out of me, she said "I need you over at my place soon. I've got a new paddle I want to try on your hot little ass." Tucking her cock back into her slacks, she walked out and whistling, over to her car. I watched her drive off and went upstairs to get dressed. I put on a tight pair of jeans that really show off my ass nicely and a tee shirt. I refer to these jeans as my "bra jeans" since the lift and separate my ass cheeks.

I decided to walk to school to get my class schedule, it is only a couple of miles and it was a sunny day. Good day for a walk.

At the registration office, I ran into Phyliss, the chubby secretary I met last night. "Hi Ryan," she smiled and said to me, "We adjusted your schedule so you can continue to be tutored by Dean Carter and me on Wednesdays." Looking at my schedule, I saw that my classes ended at noon on Wednesday. She turned and walked down the hall toward Dean Carter's office where I saw the Dean leading a young man into her office. Phyliss went in and closed the door behind her. I chuckled, knowing what was going to happen in there and it would be my turn tomorrow.

I decided to stop by the coffee shop on the way home to see Gina. It was only a short way out of the way. Heading over there, I smiled as I walked in and saw her finishing up an order for a customer. There were about a dozen people sitting around drinking and chatting and I got some lustful looks as I walked up to the counter. Seeing me, Gina got a big smile on her face and said, "Hey hot stuff, what brings you in?"

"Hi baby," I said, "An iced latte and a chance to see you."

Gina asked the other girl working with her to fix the latte and looking me over, said, "You look great. I'm glad you came by."

Blushing, I just said thanks and took my drink. The other girl working with Gina was obviously checking me out, staring at my round ass in my tight jeans.

Gina said to me, "I remember the first time seeing you, it was here. And then seeing you and Julie in the office really hooked me on you."

Giving her a big smile, I said to her, "I'm glad. Is the office empty now?" Biting my lower lip.

Gina said to the other girl, "I'm going to take a break. I'll be back in a bit." And taking me by the hand, led me down the short hall to the office. Once in the office, we were in each other's arms, kissing passionately with hands groping. Her hands were on my ass and mine were on her breasts. I let my hand slide down and squeeze the hard bulge in her pants and she began to unfasten my jeans. Soon I had her pants undone and slid my hand inside and wrapped my fingers around her rock-hard cock. She moaned and pushed my jeans down and squeezed my bare ass.

"Turn around," she ordered, "I want you just like Julie did."

I turned and bent over the desk. Gina let out a low whistle looking at my still red ass cheeks.

"Still red from last night," she said, giving them a squeeze.

I gave her a surprised look and she smiled. "Your mother sent me some photos. We've talked about you like it rough before."

Picking up my thong underwear, she stuffed them in my mouth and gave me a hard spanking, my cries muffled by the make-shift gag.

Without warning, she drove her hard cock all the way into me, causing me to scream into my gag. Leaning over me, she whispered, "I'm glad you like it rough. I do too." And started to fuck me hard and fast. Skin slapping against skin, my cries muffled I shot my load on the side of the desk and Gina rammed into me and gave me her warm cum. The door opened slightly and the other girl stuck her head in, "Got some customers, I'll need help," she said, staring at us.

"I'll be right there," Gina said sliding her cock out of me. Grabbing my hair, she pulled me and kissed me, passionately. I kissed her back. She left and I dressed and cleaned up our mess. I walked out of the office. Gina was talking to Iris and Gantz, a couple of the girls from Futa House that I recognized. I walked up and stood beside Gina, she put her arm around my waist and I snuggled against her.

"Iris has offered to drive you home babe," Gina said.

Smiling at them, I just said, "Okay but I don't mind walking."

Iris gave me a lustful look and said, "You are safe with us. Gina has said your ass belongs to her and we don't mind driving that way."

"Great," I said, "Let's go."

I gave Gina a quick kiss on the cheek and followed Iris and Gantz out to the street. I got into the back seat of their old coupe, Gantz got in the driver's seat and I was surprised that Iris got in the back with me. As we drove off, Iris looked at me with a smirk on her face. "Your ass belongs to Gina," she said, "But she said nothing about your hot mouth." She pulled her hard cock out of her jeans, grabbed my head, and pulled it down to her lap.

"Open up bitch," Iris ordered, "Suck it."

I opened my mouth as Iris pushed my face down onto her crotch, her cock sliding into my mouth and throat. I placed my hands on her thighs and let her hold my head and control the flow. She'd push me down, her cock sliding into my throat, and hold me there until I tapped on her thighs, then she'd pull my head up to let me grab a quick gulp of air then shove me back down on her cock. She kept this up as Gantz drove us around and around the campus, slowly up and down the narrow streets. I'm sure anyone could easily see what was going on in the backseat. Soon Iris started bucking her hips and moaning loudly.

"Oh yes bitch," she cried out, "Take it. Take my cum." Holding my head down, she shot a nice load into my mouth which I swallowed every drop.

Gantz pulled over and put the car in park. She said, "My turn." getting out of the car. Iris got into the driver's seat while Gantz got into the back with me. She pulled out her cock and it was the biggest cock I've ever seen -- at least fifteen inches with a large head covered with precum. Looking in the rearview mirror, Iris saw me staring and chuckled. "We call it boy ass destroyer," she said as she drove.

I leaned over and took the head in my mouth and began sucking on Gantz's massive cock. No way could I get it all into my mouth, but I did my best. Gantz leaned back and enjoyed my efforts, letting me do my thing. After a short time, she placed her hand on my head, holding it in place while she shot a big load, I swallowed fast, trying not to lose a drop.

Finally, I sat up while Gantz put away her monster cock. Iris asked where I lived and when I told her, she said, "You must live close to Gladys."

Surprised I told her I did and how did she know her. She explained, "Gladys used to live at Futa House years ago when she was a student. She continues to support us and even drops off boys for us to play with after she is done with them." That got a big smile from both girls. Soon we pulled up in front of my house and as I got out, Iris said to me, "See you around cutie. Maybe someday Gina will let us have a shot at your hot ass."

"Again," added Gantz, with a smile.

I gave them a weak smile and started walking up the driveway as they drove off.

As I neared the backdoor of the house, I heard a car horn honking. I turned and saw grandmother's car pulling into the driveway. Smiling I turned and walked toward it. Julie got out of the passenger side and walked quickly to the backdoor of the house.

"Hey bro," she said passing me. I continued to walk to the driver's door where grandmother was getting out. As I got there, she pulled me into her arms for a big hug and a quick kiss.

"I thought you were coming tomorrow," I said looking into her eyes, pressing against her.

"Julie needed to see Sally and I needed to see you," she said, squeezing me tight against her, "We couldn't wait any longer."

Giving me another quick kiss, she said, "Help me with the bags." going to the trunk.

I grabbed two bags, one for Julie and one for Granma and she got the other one. We went in the house and upstairs. I went to Julie's room to drop her bag off. She was already undressed and I spent a moment enjoying looking at her trim body and big cock.

"Tomorrow, bro," she smiled at me, stroking her cock, "Tomorrow I'll give it to you."

I smiled and went down the hall to my bedroom. Grandma was lying on my bed, back propped up against the headboard, nude. Giving me a big smile, she said, "Get your clothes off and get over here honey. Grandma wants her boy."

I quickly stripped off my clothes and climbed up onto the bed between her legs and up to her face. We kissed passionately, our tongues wrestling each other. I dropped down onto her large breasts, cupping each in a hand, taking a large nipple into my mouth, sucking and licking it while I pinched the other one. Moaning, grandmother said, "Oh yes baby, that feels so good."

I kissed down her belly to get to her huge cock. The head was leaking precum which I licked up. Running my tongue down her cock to her large, smooth ball sac. I spent a few minutes licking, kissing, and sucking on each one. Then I slid my lips back up the underside of her cock and took the head into my mouth. Looking at her, my eyes on hers, she staring at me lustfully, I pushed my mouth down on her cock, feeling it slide into my throat. Then I slowly started up and down, sucking on her hard thirteen-inch meat. After some time enjoying this, I pulled my head up and climbed back up on her, my knees straddling her hips. I leaned forward and kissed her and reaching behind myself, guided her hard cock to my eager hole. Slowly I lowered myself, feeling her cock push into me. Staring into her eyes I kept going, lower, until I was sitting firmly on her hips, the entire cock buried in my tight hot hole. I placed my hands on her breasts and began to rise and fall on her, slowly riding her cock. She had her hands on my hips, guiding me, encouraging me. We stopped in mid-thrust when we heard another voice.

"Hello mother," she said, "You came early."

Looking over my shoulder at the doorway, I saw my mother standing there smiling at us.

Under me, grandmother said, "Yes, I needed to see my beautiful grandson and couldn't wait." As she lifted her hips, thrusting her cock back into me.

Taking a moment to watch us enjoying each other, mother said, "I'm going to treat us to dinner at Maria's. I'll go clean up while you finish up here." And she turned and left.

I continued to ride up and down on grandmother's cock and she began to meet my downward hump with a thrust up into me. Soon we were pounding away fast and hard. Holding my hips, she held me down on her while her cock pulsed as she shot a load deep in me. I collapsed down on her, my head laying on her breasts. She ran her hands up and down my back, stroking me. I lifted my head to look into her eyes and she kissed me, her tongue playing in my mouth.

"Maybe we should go clean up," she smiled at me.

"I love you, grandma," I said to her.

"I love you too baby," she said, "Very very much."

Slowly we disentangled and climbed out of bed. Holding hands, we walked naked down the hall to the bathroom. Just as we got there, mother walked out, naked except for a towel wrapped around her head, her large cock swinging between her legs.

"Try not to take too long," mother told us, "I'll make a reservation for us."

Grandmother and I climbed into the warm shower and proceeded to wash each other, warm soapy hands running over the flesh. When I reached down and started to stroke her cock with my soapy hands, she chuckled and said, "Let's let that go until tonight when we'll have more time."

Giving her a big smile and one more squeeze of her cock, I said, "Okay grandma, we can do that later." We got out of the shower and dried off. Grandmother looked at my little cock, which was rock hard.

"Poor baby," she said, "You didn't cum yet. Let grandma take care of that for you."

She sat on the toilet and pulled me to her and leaning forward, took my hard little cock into her mouth and started sucking. It didn't take very long I was so horny. I shot my load into her mouth and she swallowed it all. Just then mother walked in, now dressed, and smiled at us.

"I decided to have my dessert before dinner," grandmother joked.

"And you sure to love your dessert," mother laughed back at her. "Get dressed and we'll go," she added.

I put on another pair of tight jeans and a polo shirt. Meeting them downstairs, the three of us headed out. The drive to the restaurant was short and we parked in the lot. I walked between the two ladies, my arms in theirs.

"Out for a night with two beautiful women," I said, "How lucky can I get."

We got our table and they ordered wine. I was too young for the alcohol and gave mother a disappointed look.

Squeezing my hand, she said, "Don't fret. We'll have some when we get home."

Dean Carter walked up and greeted us. Looking at me, she said, "Ryan, I'm looking forward to our tutor session tomorrow."

I smiled and said, "Me too Dean Carter."

Mother asked if Dean Carter wanted to join us. She chuckled and said, "Thanks, but no. I'm taking one of the busboys home with me tonight. Time for me to go."

Looking around, I noticed there were half a dozen young busboys scurrying around, all wearing a short apron over tight shorts and a restaurant tee-shirt. Seeing my confused look, mother laughed and placed her hand on my thigh under the table. She explained that Maria always had extra busboys as most of them got picked up and taken home by her female customers.

Mother added, "Gladys and I have picked up our share over the years. A great place to get a boy for a night of fun."

As I watched, Dean Carter was joined by Phylis and they took one of the busboys by the hand and led him out of the restaurant.

With a smile, I said, "Maybe I should get a busboy job here this summer."

Giving my thigh a squeeze, mother said, "Perhaps. But Aunt Sue already has a summer job for you at her advertising agency."

Soon we had our meal and left. I saw four other busboys being taken away by pairs of ladies while we were there. I asked mother why it always seemed to be pairs of women and she told me they all really loved to share. Grandmother said, "Yes, we do. Time for us to go home."

We returned home and mother said she would get us all some wine. Looking at me she said, "Honey, go put on the new sleep outfit I laid out for you."

In my room, I stripped off my clothes and pulled out the new outfit. A pair of loose-fitting shorts made out of the most transparent material I've ever seen, in a light tan color. The tee-shirt was made out of the same material. I put it on and looked at myself in the mirror, the outfit didn't hide very much at all.

I walked back down into the living room. Mother and grandmother were sitting on each end of the sofa, sipping their wine. The wine bottle and an empty glass were sitting on the coffee table. When they saw me walk in, they both smiled.

"That looks very nice honey," mother said, putting down her wine glass and picking up her phone. She snapped a photo as I walked over to them. In the middle of the room, she told me to stop and turn around. I did and looking back over my shoulder and smiling, she took another photo.

"Turn around a few times for us," grandmother said.

I did as she asked, spinning around in front of them.

I walked over and sat on the sofa between them. Grandmother poured me a glass of wine and handed it to me, then placed her hand on my thigh just above the hem of my shorts. Her eyes were on the tent in my shorts caused by my erect little cock.

Turning to me, mother said, "You look so nice in your new outfit I had to send some photos to some friends."

She then sat back and sipped her wine while stroking the back of my neck. We three chatted, mostly about what we did at the reunion and about Grandmother's search for a new home near us.

After my second glass of wine, grandmother squeezed my thigh and I spread my legs a bit more. She then slid her hand up under my shorts and gripped the head of my little cock between her thumb and forefinger, twisting them back and forth. My moans were all that mother needed to hear.

"I think it is time for us to go upstairs," she said, standing and taking my hand. She lead me to the stairs as grandmother followed. We went up into my bedroom and there, grandmother pulled my shirt up over my head and pushed my shorts down, which I stepped out of. Standing completely nude in the middle of the room, I looked over and saw mother had taken her pants off and was lying on the bed, legs spread, her hard cock lying on her right thigh.

I crawled onto the bed, between mother's legs. Leaning down, I took her cock in my hand and holding it up, ran my tongue across the tip, tasting her precum. Then looking into her eyes, I took it into my mouth, lowering my lips, taking half of it, holding it, sucking and licking. Looking at her.

I felt grandmother crawl onto the bed behind me. I felt her hands on my ass cheeks, spreading them. Then her tongue, ran up and down my crack until it started to push into my hole. I moaned onto mother's cock in my mouth as grandmother started to tongue fuck my eager hole. After a while, grandmother withdrew her tongue and replaced it with her cock, I felt the large head push into me and she continued until she had it all in, her body pressing against my hips. Holding my waist, she then started in and out of me, slamming in hard. Mother meanwhile, holding my head, started pushing her cock in and out of my mouth in time with grandmother's hard fucking of my tight ass. The two of them got into a steady rhythm, fucking my mouth and ass.

I was helpless between them and loved every second of their domination. Mother went first, shoving into my throat and holding her cock there, shooting a large load directly into my stomach. Before she pulled her cock from my mouth, grandmother yelled and shoved her cock completely in me and I felt her warm load flood my insides. All three of us were panting, short of breath. Mother slid her cock from my mouth, I fell forward, exhausted. Giving my ass a hard slap, grandmother slowly pulled her cock from me and lay down beside me. Standing and looking down at us, mother said, "Sleep well you two, I'll see you in the morning," and turning she left. Grandmother pulled me to her, hugging me, kissing my forehead. "Such a wonderful little grandson you are. Grandma loves you so much."