Dirty Bedtime Stories, Liston Ch. 01

Story Info
Exploring curious fantasies on his first date.
4.5k words
4.31
4.9k
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter One: A date night bliss

Grandpa's male maid Deepan been on leave for two weeks. For the time being, his needs been fulfilled by our house maid Sherley. She has been a part of our family for the past six years. Uncle liked male maids and he doesn't really let her to bathe or clean his private parts. Grandma passed away when I was just a kid. Grandpa been the back bone of our family for long. He was healthy and really agile considering others of his age.

Five years back, grandpa met a terrible road accident. Even though he gradually reclaimed his health, he became less active from other family matters and business. Soon he handed over the family torch to my daddy. As daddy became more dynamic in business and financial matters, grandpa became the watchdog of our home.

Me and grandpa shared a special bond for years. The bond grew as I became an adult. Grandpa at his age of early sixties, shared a lot of young and influential thoughts with me. Two months back, he fell from a bicycle while went for evening ride. He took a hard hit on his hand and it took almost a month to get fixed. Deepan was appointed for taking care of him.

The caretaker was a young boy, at mid-twenties. He was lean and really peppy. He was really good at taking care of older people. We had nothing to worry about grandpa since his arrival. He will bathe grandpa, shave him and will do the prescribed physiotherapy for his hand.

One fine evening, I was obligated to step into grandpa's bedroom. It was the time when grandpa was supposed to be alone. The view inside the room shook me so hard, I stopped there frozen. My eyes literally popped out of my head. The spectacle hit me so hard, for days it gave me sleepless nights.

Now, before judging my grandpa and his vague interests, there is some things needs to be established. He might me old but he was well built and healthy. He never sits ideal at home, always engaged in little things. Since I been really close to him, I kind of know his likes and dislikes. Once he openly admitted to me that he liked boys of my age. He admitted he has been with other men, young men to relieve the physical abstinence that created from the absence of my grandma.

A year back when I just got to nineteen. From my college hostel, I called by buddy Sebastian, on an evening. When I asked him where is he, he suddenly replied that he is with my grandpa at my home. The way he described the situation, it seemed all shady. But when I heard another voice from the other end, I could not believe my ears. It was my grandpa. I don't know what made me more worried. I was jealous of my buddy and I felt really possessed with the whole shady situation.

Back in my college hostel, I was facing another dilemma. I have been curious for couple of years and I was in the verge of coming out. One of my senior Jacob called me out for a late-night chat at a nearby Bar. He has been tailing me for months. I tired to avoid him, but he was like a cool stalker everyone wish to have. He was cute and handsome. But he seemed a bit too aggressive for a first timer like me. That night after I heard my grandpa, taking on my buddy at my own home really pumped my testosterones.

I was too restless the whole time. I finally decided to share my thoughts with my, not so friendly roommate, Shawn. But for my extreme surprise, he seemed too calm handling situations like this. He reassured me and told me to be myself and never be afraid to try new things. He knew that Jacob has eyes on me. He told me earlier that Jacob is a nice guy, especially considering him among other seniors he hangout with. Besides, in Shawn's eyes, our interests and curiosities seemed coincided.

I was confused for a second. Shawn, for the last months been a totally different person to me. I don't know what triggered him, but he swiftly changed from an absolutely bully, self-minded freak to a friendlier and more somewhat caring roommate, anybody expected to have. He had been my roommate for last seven months. During those periods, he never cared anything other than him. He always keeps his things to himself. He was not at all friendly and almost everybody loathes him. We actually started speaking openly like friends or roommates, just weeks back.

I still remember when I shared my things with my grandpa, he repeatedly asked me about my roommate and his interests. I was not that lucky to have a good caring buddy, so I told him that I practically don't have a friend at hostel. As per my grandpa's suggestions I tried to become closer to Shawn, but he always keeps a distance. His social skills were a wreck, worse than mine. Once I openly told him about my bi curious nature, he surprisingly accepted it. He said his cousin is gay and he is oaky with it. That was the first major sign that he showed. I told him my closeness with my grandpa and he adored it. Those acceptances made me try more with Shawn, and it paid off. He looks and feels like a much changed, desirable persona. Even though he became more closer to me as his roomie, he stood the same grumpy idiot, outside those hostel room walls.

That night, I went out with Jacob for dinner. We had really light dinner. After that, we hit a bar and had couple of beer. He seemed really nice guy. We had a lot of things in common. I had to admit, he seemed so adorable and friendly, I wished I should have said yes earlier. The more I spend time with him, the more I craved for him. I was going through a whole different mood that night. I still can't believe how I got the nerve to positively respond to his flirty inquiries. I never been so bold or gutsy ever. That night I was different. Maybe it was the booze, but want to go full swing.

"Among the whole fauna, when you picked me?" I asked him softly as we almost finished my second bottle.

It was dark and disco music was playing through the speakers on the walls of the shabby old Bar. The time was around nine and the place was about to close. Hearing my curious question, Jacob just shrugged his shoulders and smiled.

"Was I that predictable?" He knew I got him and he responded in a funny way.

"I mean its been like two, or three months you started following me, asking me, pleading me for a 'date'. You are my senior. You could have tried any other way to bring me to you, why the wait? I popped the bubble pretty hard.

"Well, I could have, but, that would have been wrong, this feels..." he paused searching for pleasing words.

"Right?" I tried to complete his broken sentence.

"Pleasing!" he concluded with a charming smile of confidence.

"That would have," I softy wiggled my head in accord.

"So then tell, why me?" I just want to hear, why he chosen me.

Jacob just giggled again. Finishing the rest of the bottle he stood up.

"Let's go Liston!" He put some cash on the table and took my hand.

It all happened so fast I was bamboozled. I looked at his hand and its gripped hard, strong. I stood up with him.

"Are we going?" I asked his as I followed him.

"Yes, the answers for your questions are not here!" he mumbled.

"Let me take a leak first, my tank is full" I pointed out.

"Okay, let me show you the rest room," Jacob suggested.

Jacob walked ahead of me slowly. I followed him holding on to his wrist. We were about to enter the rest room, then we saw the cleaning board which suggested to take the washroom on the other end. I head felt really heavy. I was a bit tipsy. As we passed thought the corridor, something suddenly triggered the memory of the last phone call I did to my buddy.

Inside the dark rest room, I took a long leak emptying my bladder. I went to the basin and washed my hands. I was kind of nervous. Jacob stood pretty close to me. The tension as pretty high. My heart was pounding.

"Can I kiss you?" Out of nowhere, Jacob asked me softly.

I looked up on to the large mirror in front of us. Through the reflection I looked at Shawn's glowing face. I can clearly see myself blushing. I nipped my lips in nervousness. I tired to bring a smile on to my trembling lips. I was so tensed, I stood cold.

Hugging him tightly around his warm body, we took a swift ride to our hostel in his bike. I was not sure what's gonna happen from then on. I was in bliss. I never enjoyed that notion ever in my life. It was kind of strange, tingly and supernal. It was neither romantic nor sexual. I felt so jumpy, it felt like I received the perfect gift on my birthday.

It was my first kiss. It took me to nineteen to get my first. It may not be the perfect one or the best one, but the feel it induced on me, sending shock waves through my body, twitching my veins. It just took, I don't know may be five seconds or so. I was too nervous and spooked to face him when he brought his charming face closer to me.

When Jacob pressed his torso against me, I closed my eyes in a flash. Within seconds I felt his thin peppy lips pressing against mine. I took a quick deep breath, stretched my eyebrows and tried to lean back a bit. I kept my eyes tightly closed. Jacob followed me and his lips pressed harder on me. Mine was thicker and more reddish. Before I process things in real time, he moved back his head releasing his beak form my tender cherries.

I had no idea how to react then. I opened my eyes, took a deep breath again and softly giggled in relief. Jacob looked alive and excited. I smiled, this time relieved.

"Let's go!" I suggested, just to ease the tension a little bit.

"Okay!" Jacob smiled gently and made way for me.

When we reached our college hostel, Jacob followed me till my room. He asked me to think about another date on the coming Saturday, five days later. I nodded my head and knocked the door. Shawn sprinted in to open the door. He was in his favorite blue shirt and brown shorts. When he saw Jacob walking away through the corridor, he giggled laud. I went inside the room and a took a long hard heave of breath before I sat down on the chair removing my shoes.

"Wow! You look exhausted!" Shawn shouted in sarcastic tone.

I looked up onto his face and laughed.

"Shut up!" I said calmly.

"So, how was the date?" he asked in jumpy tone.

Being my roommate, I never seen him intruding in to my personal space so enthusiastically.

"I told you it was not a date!" I shouted gently, and tried not to laugh.

"Oh, you poor thing!" he mocked me.

"You expected it to be a date, eating around the candle light, hearing romantic music and dance under dim light?"

"Stop you, jerk!" I threw my shoe at him who kept on taunting me playfully.

"Oh, you smell booze! You got drunk?" he seemed shaken.

"Its just beer!" I clarified as I removed my socks.

"Oh hho! Just beer, what all just things happened after beer?" he continued.

"What? Nothing happened!" I tried to convince him, but I failed miserably.

"We just had food and couple of beer, that's all," I shrugged looking at him. I find it hard to keep hiding things.

"Oh really? Then why you look and sound like a felon who is trying hard to hide some dirty secret?" Shawn was too smart and wicked. He was kind of on to me.

Shawn seemed too keen to know these things, especially after we started sharing my personal interests.

"What secret? Nothing!" I giggled as I stood up and walked to the wash basin.

I opened the faucet and washed my face with the cold water. Shawn followed me. He was not letting this thing go anyway.

"What? Nothing happened, he just asked me for another date, that's all? "I tried to be kept it simple and conclusive.

"Oh! So, it was a date! you naughty, dirty Liss!" Shawn caught me there for sure.

"Stop being an ass now! "I pushed him gently and giggled laud.

"Okay, cut the crap now? Did you guys make out?" Shawn dived right in.

I was not fully out of my tipsiness. There was so much excitement inside me, I had to vent it out somehow. I could have called grandpa and share this with him. But that night, he was in oblivion.

"Shawn! NO! we didn't make out, come on! keep it down now!" I tried to calm him down.

"Then?" he probed again.

"Well, we may have kissed, just a little bit!" I find it little bit hard to explain things to him.

"Kiss?" that's it?" He wondered.

"Wow! That's it? You all getting blushed because you got a kiss?" Shawn made It look like nothing.

"Yeas, that's it" I replied with a bit of anger.

"So, all this buildup was just to hide a secret kiss?" he laughed sarcastically.

"Yea, that's all happened, I told you it was nothing," I tried to comprehend my pride.

"What were you expecting? Get my ass tossed?" I asked him hysterically.

"Okay okay! good for you. So how was it?" he seemed a bit less intimidating and bit friendlier.

"It was scary! It was my first kiss!" I calmed down.

"It felt special," I remembered the moment Jacob's lips pressed against mine.

"See I told you, he is a nice guy. Have you ever seen tailed any other boys I our college"? he clarified and reminded the reason why I went out with him the first place.

"Exactly, that's what I asked him too," I shared my enthusiasm.

"And?" Shawn asked curiously just to see my expression.

"He said nothing, he said he will tell me later!" at that moment I knew, I let it out of my hand.

"Of course, that why he asked you for another date, not for poking you with his stick," he laughed devilishly.

I just couldn't get angry on that. I may be expecting exactly that when I go on the next date. In fact, I versioned that during the return bike ride. I thought, after reaching back from the bar, he might take me to his hostel room. I might get my first ever intimate time of my life, kissing, licking, sucking, fucking.

"Why ask him, I will tell you," Shawn put on more serious face.

"He thinks you look adorable, you sound soft, you are calm and friendly, your lips look so tender and red he crave to take a bite," Shawn concluded.

I had to say, it feels good to hear praise from others about you. Under the circumstances, they all felt like a cherry on top. Especially the end part when he praised my body shape which really shook me. Hearing flirty commends from Shawn really raised some serious questions in my mind. Although Shawn been a regular visitor in my wicked mesmerisms, I never thought of his as a plausible contender. He was so restricted to himself, for the first four months, I have never seen him even shirtless in the hostel room. Once there been this shift in the paradigm, things changed. Only then I actually included him in my impious parallel world.

"What?" I laughed out loud.

"Stop kidding!" I told him after calming down a bit.

"No, I don't. I am serious!" Shawn defended.

"And most of all, something I knew as your roomie. You got a pretty tight ass under those pants!" Shawn chuckled.

"Really? You think so?" I giggled play fully.

"I bet everybody does!" Shawn nodded his head joyfully.

I paused a moment. I have heard comments about me, my body and all from other boys. But this was the first time I actually heard Shawn praising my physique. The day was already extra special and the things unrolled then, made things more luscious and wilder.

"Well, I don't know about everybody, but Jacob do," I tried to tease him a bit, just to know his deal.

"What? he said so?" Shawn suddenly turned serious.

Jacob's face became stern and cautionary, foreshadowing the enjoyment that he possessed earlier.

"His fingers were grabbing my ass when he kissed me, I don't think he need to say it!" I kidded back.

The change in the look on his face was pretty vibrant. I felt it funny to see him getting jealous.

"He grabbed your ass?" Shawn's sound stuttered a bit.

"Nobody saw you guys? He sounded really offended.

"I was inside the washroom with him. He locked it from inside. Then he hugged me. He kissed me, squeezing my tight little ass cheeks!" I just exaggerated thing wildly.

"Wow!" he sounded really nervous this time.

"Yeas, it felt awesome! I can still taste him in my mouth!" I just enjoyed watching his getting restless but trying hard to keep his composure.

"What? What you mean by you can taste him? He was not even trying to pretend to be happy anymore.

Shawn looked disturbed. But I kept my joshing smile and continued. His expressions, the heat of possessiveness and persuading jealousy gave me strange but tingling feelings. I also noticed a clear bulge getting formed inside his tight shorts.

"That's enough detailing, let me take some rest now!" I cut in the middle.

"Did you guys go all the way? Or just fooled around?" Shawn tried to get something to get relieved.

"No, you silly, not in a first date. He asked me out again, so probably coming Saturday, he might go, you know 'all the way'!" I peppered it handsomely enough for him to get some more heat.

Shawn stood there confused. He gave me the weirdest expression when I crossed him and went on to change my cloths. I felt it strangely funny just to see his face in fuming red. I never thought of it like this. He was the one who actually motivated me to go out for the date. But even for him it was hard to believe that I went ahead so far so swiftly.

"Why didn't you go all the way? I bet he got pretty huge dick for you to stick on!" he tried to be less mean, but it came out pretty grumpy.

"Who told I don't want to, it was just so late, we had to stop in the middle!" I just didn't like his tone.

Shawn sounded like a jerk, which was not something new. He got real scarcity of nice words in his vocabulary. I replied him the same way he asked me.

"And you are right again! He got a pretty huge dick, and I'm pretty sure he is dying to fill my tight ass with his bogey!" I kept the tone minder, but I started feeling his suffering pretty soon.

Shawn just stood there emotionless. His face went pale and dry. He was in shock. Something I never anticipated from grumpy roomie. I went a bit too far and I knew it instantly. I decided to apologies and tell him it's all a lie, nothing really happened. I wanted to tell him. I was just screwing around him. I wished to apologize, I was about to. I just realized Shaun's suffering, the same burn that I experienced after the shocking phone call. My buddy Sebby most probably got screwed by my dear stallion grandpa.

"Why don't I just show you what I did back there inside the washroom?" I paused.

I don't know what commotion made me took the biggest and probably the fastest decision of my adult life at that very moment. Seeing him standing in shock, I was thinking naughty in the back of my head. I was getting surprise arousal. I never even tried to hold back my feelings either. It was some level of dopamine rush. Bowing down in front of him on my knees, I held tight on to the top of his shorts. I pulled his bottom all the way down till his feet. His lean curvy manhood dangled in front of my eyes.

The view and the atmosphere were not as something I always dreamed. The throbbing brown meat hanging in front of my face, was not of someone I expected to be my first. The fear and nervousness were not something the way I predicted. There was no time for me to think hard on the matter anymore. Things already flew out of my hold.

Before giving any time to react, I took his curvy blown dick between my fingers. I spread my lips wide and engulfed his warm curvy cock head right inside. He was in shock and he tried to react vaguely. But once I began it sucking inside my warm mouth, he stood motionless. I sucked in all the air in my mouth, making forced dimples on my cheeks from inside. Touching his hairless thighs, I closed in my mouth onto his manhood. Gently releasing my lips around his cock, I crept my lips further towards his cock base. I joined both my hands together on to his pole which now throbbed inside my hungry mouth, I quickly took peak at his face. His shaft was leaking creamy and salty fluid right from the beginning.

12