Hi, I’m Conor. About me, I was born in Boston, of an Irish Descent. I’m in school. I was a very good student and have been in the top 3 of my class since kindergarten. I live with my single mom, Roisin, 33yrs. She is a very beautiful woman. My friends categorize her as MILF. She is very fair with blonde hair and green eyes. She is a little chubby, but not fat. With boobs of size 32DD, and a huge ass to go with it, she was a MILF. She has a small bakery shop near our house. She spends most of her time in the shop and looking after me. We do not have a maid so she does not have much time for dating. My father passed away 7yrs ago, and she thought that any man who will come into our life might not take care of me well. So she never re-married. Anyways, I also have my Granny, my mom’s mother. She lives an hour away from our place. She is 50yrs old, but she is still in great shape for her age. She is thinner than mom and has a breast size of 32D. She is in the postal department. She visits us from time to time. Grandpa had also passed away and Granny was in a live-in relationship with another gentleman, Andrew, of similar age.
Let’s start the story on the auspicious day of my birthday. Everyone was glad and celebrating my teens. Mom had made a special cake in her shop and brought it for the party. All my friends were also here. It was great. Since we were just teens and always horny, we almost always talked about sex. We were 5 very good friends. Joe, Kim, Jake, Raj and myself. We were a very diverse group of nerds. Anyways, Jake thought it was a great opportunity to have our first sexual encounter. Like maybe grab some boobs, kiss a girl, anything. With this in mind, Jake had brought a pill with him. He had seen his uncle uses it for sleep. None of us knew what it was called or how it should be used. We thought it would be fun to give it to someone and fool around. We were looking for someone to try this on. It was getting late and we could not find any girl to slip this into her drink. And everyone was starting to leave. Only my best friends and my family members remained back and cleaned things up.
“What a bummer,” Jake said. “We have the magic potion and still we couldn’t experience anything.”
“Yeah, man want a waste of shaving my balls” – Raj said.
“Wait hair,? What balls? Dude you do not have hair on your balls” – I said laughing aloud at him. Everyone joined.
“I do, you guys just don’t know. We Indians have hair everywhere.” – He said with pride.
“Yeah, not today my friend”
Suddenly we heard a thump in the living room and we rushed inside. We saw Lidya, Mom’s assistant chef, was on the floor. She was like oozy and fell. My mom and Andrew were trying to lift her up. Grandma was bringing her a glass of water. Mom requested Grandma to look after the kids while Andrew and herself will take Lidya to the doc. Grandma agreed. My friends were anyways going to stay with me for a sleepover so it was going to be us 5 and Grandma taking care of us. My friends and myself were watching TV and having a laugh. Grandma was sitting in the kitchen and having wine reading a book. Soon I felt a little thirsty and went to the kitchen to fetch water. Grandma had dressed modestly for the party, but as my mom left, she wanted to feel a little comfortable so she wore my mom’s nightgown. It was a little big for her. By the looks of it, she also removed her bra. She was busy reading the book and drinking wine. Lost in the words, she didn’t even notice me looking at her cleavage. Since the dress was loose the neckline was making a huge gap as she sat on the dining chair. Wao.. I thought and went back with a bottle in my hand for my friends.
“Guys, Guys,” – I whispered. “So you all were saying the party was a failure as no one could have any sort of sexual fun tonight not even a cleavage or an upskirt. I think we are in luck. Granny is in the kitchen and her melons are all huge and out. You can see like the top part of her nipple too.”
“Dude.. Score” Jake said “Let me see it too”.
Everyone left. “Wait wait.. One at a time. Jake you go ahead and bring soda, then Kim you go and bring some chips, Joe you go and bring some glasses and raj you go and bring the dip”
Everyone went one by one and came back giggling. All were excited.
“Dude why not give granny the magic drink? After all she has amazing boobs and fuckable ass.” Jake said.
“Hmm.. I don’t see why not. I’m sure Andrew was not providing her the fun she deserves. Ok let’s do it” I said. “Ok so I will go and distract her and Jake mix the meds in the wine glass.”
We took our positions and I started talking to granny and made her look the other way, While he Mixed the meds in the wine glass in her hand. It was exciting. Thinking about it made us teens hard.
Then we both came back and looked in excitement. Waiting for her to pass out. We waited and waited. In the meantime, mom called and told granny that she will take a couple of more hours, and she should get us to bed.
“Comeon boys, go to bed now it is getting late.” Granny said walking to the living room.
“Please granny, we do not want to go to bed this early. It’s my birthday, Pleaseeeee.”
“Ok Ok.. A little while more than you have to go to sleep”
“Sure granny”
Then she sat in the living room itself on the arm chair and continued reading.
Raj looked at Jake, gesturing when will the pills take their effect. He gestured he does know. So we waited, playing games on TV.
Soon we saw the book in granny’s hand was closed and her neck was to one side on her shoulders. She was asleep. Finally. Jake did it.
“It’s time for the Birthday boy to unpack the gift”. Jake Said laughing. I gestured to keep quiet. We didn’t know whether she was in deep sleep.
I stood up and went to her. Shaken her shoulder. She didn’t budge.
“All right, we are on..” Kim said giving a high five to Joe.
“So what’s next” Joe
“I want to see her boobs, pull her nighty front,” Raj said. His dick was already hard. I pulled her nighty front and we all gazed her boobs resting on her stomach as she sat there.
“Nice” Jake said. “Touch it Conor.. Let’s feel the boobs”
I slowly kept the nightly upfront and slipped mine hand inside. I groped her huge boobs. Her boobs were so big. I would need both my hands to cup them completely, I thought. Rubbed her nipple and pinched them softly to make them hard.
“I’m next.. I’m next” Raj said as he pushed his hands inside her nighty. “Wao.. Boobs. White women boobs. Amazing” He started to grope them a little too hard. This made Granny adjust a little in her chair. We all froze. False alarm. She was still out.
Then everyone took turns squeezing her boobs.
“Let’s lift her nighty so that can take a peek between her legs.” Jake
“Alright.. Let’s do it..” Kim
“Pussy pussy pussy” Raj said with excitement as we all sat on the floor in front of granny’s chair. Then we slowly lifted her nighty. She has fair legs, some hair for sure, but it didn’t bother us virgins.
“Wao, she is wearing a lacy pink panties.. Like she was expecting some action tonight from Andrew.” Raj said, laughing.
“Don’t worry we will give her some action,” Jake said. Slipping his hands under the nighty and moving her panty to one side. Her Vagina was clean shaved. Alteast the part that was currently visible to us.
“I cannot wait any more,” Joe said taking his dick out and he started humping Granny’s legs.
Seeing this others too started to undress. Now we all were on the floor naked with our hard but small dicks in our hand. Jerking touching granny’s thighs and legs.
Jake took the next step and folded her nighty to her waist. He again shifted the panty to one side and slid his one finger inside her pussy. He then immediately pulled it out and smelled it.
“Pussy finger, alright” Everyone took turns putting a finger inside her pussy and smelling our fingers. The other hand was busy jerking. It was great. Every teenager’s dream.
“I want to taste it,” I said and stood on my knees and put my head in between her legs. With one hand I was holding her thick thighs and with another, I was squeezing her boobs. It was so arousing. I got carried away and I became a little too vigorous.
Suddenly I hear a voice.
“Easy Tiger”, it was granny. I froze. Didn’t know what to do. I looked at my friends they all were on their knees covering their hard dicks with both hands.
“So you guys like to fuck your sleeping granny”. Sleepy?? I thought we had drugged her?
Apparently sleeping pills do not have much effect on granny. She is used to them. She was just asleep as she was tired. Oops! Now what.
I slowly lifted my head and said. “I’m so sorry granny, I didn’t want to wake you up.”
“Too late I was up since the first time you lifted my nighty up” She said.
“Dude, your granny is a slut, she was enjoying young boys touching her.. Nice..” Jake said again jerking his black dick.
“Of stop, Not anymore. Well I used to be when I was young.” Granny said, “I was 17 when I had your mother, so….” She said looking at me.
“Go Granny..” Raj Said humping grannies legs again.
Granny smiled and said “So you all want to experience a women? I too have been starving for a good fuck. I will teach you all the in’s and out of sex, but you have do exactly what I say”
What next? That was enough for all of us to pounce on her and grabbing and licking her body. I pulled her nightly down and started sucking her boobs, Kim followed me. Jake Started kissing her and fingering her. Raj and Joe took her hands and made her grab their junk. We were in heaven. We never thought that tonight is going to be the night were were losing our virginity.
Granny was moaning because of all the action and attention given to her. She then pushed us all a little far and stood up. Removed the nighty. This was the first time we were looking at her massive boobs. We sat there on the floor as she turned around and gave us a show. She bent over and slowly pulled her panties down. All the while she was looking back at us. She was enjoying the excitement is our eyes. Then she again sat down and I left to lick her pussy. Raj and Joe again gave her the dick. Kim was licking her thighs and Jake was still kissing her and jerking hard.
Soon she took Raj’s hard dick and put it in her mouth. She was thrusting her pussy up and down as I was licking her hard. All this made Raj’s uncut dick very excited and he came in her. Granny was not expecting it, she just smiled and swallowed it. Joe saw the opportunity and turned her head the other side and showed his cock inside. Jake took Raj’s place and was getting a handjob. A couple of moist in and out of Granny’s mouth and Joe too came in her. She kept looking at him and smiling as he unloaded his cum in her. She happily swallowed that too. Jake was next, again in few secs he too came. Next was Kim. And Bam! Two strokes and done. Granny had already swallowed 4 loads, I stood up for my turn. Granny stopped me.
The birthday should get it special.
She made me lie on the ground and started sucking my dick. She was on her all fours. Her boobs were hanging and touching my thighs.
Raj started to play with them with one hand while still jerking his dick with other. Granny gestured Jake to lick her pussy. Jake obeyed. My small thin dick was inside my granny’s mouth. She was sucking and making rotating motions. It was hot. It didn’t take me a min to cum inside her. Worth it.
“I hope you boys had fun” She said. “Now who is ready to fuck my pussy?”
“Me.. Me.. Me..” We all said in a unison. She laughed wiping her mouth with mom’s nighty. A little cum was stuck to her lips.
“Well It will be a huge step for you guys right. You guys could say that you have had sex. So it will make you guys really popular. What are you guys willing to do for me?” She said.
“Anything” We said.
“Though you guys have lot of energy and I’m sure you guys will last a little more this time, but still your guys dick are too small and thin for me. I can two of you together.” She smiled looking at us one by one.
“But I want to see how ready you guys are for this big step. So, who ever suck others dick, can have a go with my pussy” She said.
I looked at Jake and were thinking about it, When we turned around we saw Raj sucking Joe and Joe sucking Kim, and Kim was trying to reach my dick to suck it. Well, Pussy is more important than sucking friends dick. So why not. So I let Kim suck me off while I sucked Jake. It was weird. Moments ago I was sucking my granny’s pussy now Jake’s dick. It was different for sure. The taste, the smell. Weird. But not bad. Granny was turning on by this, she was sitting on her chair and rubbing her clit vigorously and squeezing her boobs.
Soon she was ready, she kicked Raj on his has, motioning to come and fuck her. He stood and jumped at the opportunity, She spread her legs apart and took Raj’s whole body and wrapped it around. She sat there and Raj was trusting his dick in and out of her. She slowed him down.
“Boys look here, go slow, no need to hurry, enjoy it and make sure women is also enjoying.” She said. But were were high on sex. He did slow down for a moment but soon started to fuck her hard. She was moaning all right but in like a min and he made weird noises and came in her. She laughed. He fell on her boobs. She comforted him. “Good job Raj” She said just to make him happy. He kissed her boobs and sat on the couch jerking. Next Joe and Kim turns. She made both of them fuck her together. She was enjoying it. A min later my turn came. She gave me a chance alone, I fucked her, it was not enough, she asked Jake to join too. I could feel her pussy juices around my cock. Jake’s dick and mine were going in and out at the same time, behaving as one. She was feeling something. Something she hadn’t felt the whole night. Jake’ black dick was the biggest among us, but still like 5 inches. Combined girth of our dick made her happy. She closed her eyes and was playing with our hair. We were garbing her boobs for grip and fucking her hard and then she made a weird noise. Wait.. What we were able to make Granny cum? Yes, we did it. Yes, it took five of us to reach there but we did it. She was spilling her pussy juices and flowing through her thigh and making her chair wet. Soon we came too. One by one we pulled out. We all sat there tired. All sweating. After a min granny smiled and got up. She took the nighty and cleaned herself. We were still playing with our dicks. We wanted more. She started to go to her room “Well boys, it was fun, but now you guys need to go to your room and sleep. I’m sure you all are tired.” She said, pinching my chicks. “But granny, I have one more load in me” Raj said. “Yeah!” We all joined.
“Well, ok come here” she knelt down and started to jerk us off while we played with her boobs. Jerking two boys and sucking one, Granny was speeding things up. And like that, we came on her boobs and her face. Waooo… What fun was tonight. I stood with my hands on my hips and watch granny stand up and clean her face with the nighty.
“Good night boys” She said gesturing us to go upstairs. We were tired and all drained out. We got more than we came wished for, still we didn’t want to leave. But we did. We all lifted our clothes and walked to the stairs still looking at my naked granny who was smiling and wiping herself.
We were really tired and we to fall asleep as soon we hit the mattress. Next morning I woke up with a smile. I could hear mom’s voice. So she is back. We all got ready with huge grins on our faces. No one talked much and just looked happy. We were men from now on. We went downstairs for breakfast. Mom welcomed us with a smile as she placed the plates for us. “So boys, had fun last night after we left?” Before we could answer, granny replied with a naughty look in her eyes “Your mom does not believe that boys can have a lot of fun when they are under their granny’s supervision”
We all smiled and said “Best night of our lives”.
We knew it was not over.. This was just the beginning of our new adventures….