Learning from Older Men Pt. 02

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This tale is a partially fictionalized account of my first time being seduced and sucking off an older man following my introduction into the world of gay sex online.

Names have been changed as well as locations but the following story is based off of real events.

By the end of 2013 I had discovered that I was sexually attracted to men following a chance encounter on a webcam chat website earlier in the year. Following this experience I stayed in contact with the man through Skype and slowly began to collect other partners for webcam sex, always much older men. During the same period I decided to grow my hair out long, in hindsight I probably did this to make myself appear more feminine for those men who like that in a young guy but at the time I didn’t really think about it. At any rate this simple change to my hairstyle would eventually gain me the attention of my older history teacher Mr. Phillips.

Now Mr. Phillips was a gruff man, a decent teacher but he had a reputation for being fearsome when challenged and of generally mocking those students who in some way displeased him. I was a pretty good student and I’d always done well in his class so I’d never really had a problem with him before until one day he noticed that my hair had grown longer and decided to call me out about it in front of the class.

“Your hair’s getting pretty long you know, what are you a hippy now?”

He chided me.

“I know, I know, it makes me look like a girl.”

I said, attempting to disarm any emasculating comments of which I’d already received a number from other classmates.

“I’m sure you’d make a good girl.”

He laughed along with a few other classmates, I felt my whole face burning. What did they know about me? I’d spent the night before dressed in a fishnet bodystocking that I’d stolen from my older sister, dancing in my bathroom for an extremely horny businessman and father who liked to get off watching me after work. I felt as if they could all see those memories written across my face.

A few of my classmates made jokes about it afterwards, warning me that I was going to get fucked by Mr. Phillips and how it sounded like he was into me. But actually it was pretty much consensus that Mr. Phillips wasn’t gay and they were just making fun of me rather than seriously insinuating that he was interested in me. But as the class went on I found myself wondering about him. I’d thought about a lot of my different teachers at one point or another and actually I’d once had a nice long wank session picturing myself sucking off Mr. Phillips. He was a large man with a broad chest and a nice beard. In recent years he’d gotten a bit portly but it only made him more attractive to me and I’d always assumed he probably had a quite a nice thick cock. I kept sneaking glances at him throughout the lesson but he didn’t seem to be paying me any more attention.

As the class started to file out of the room at the end of the lesson I lingered slightly packing my things away slowly and when it was just the two of us alone he suddenly spoke up.

“Oh by the way I’ve got to talk to you about your essay, could you come visit me at the end of classes?”


I stammered, slightly embarrassed by his earlier comment still, and hurried out of the room before he could say more. Throughout the day I agonized over his earlier comments wondering if he was actually trying to send me some sort of coded signal. I was of legal age but he could still get in a lot of trouble for sleeping with a student, at the very least he would lose his job. Even if he was interested he’d have to be really careful. Then there was the part of me that thought I might just be going a bit mad from sexual frustration. Sure I found him attractive but there was nothing to suggest that he was attracted to young feminine guys other than that one mocking comment. Still as the day wore on I couldn’t get him out of my mind.

Eventually my last class finally ended and I made the way across the college to his classroom. The other students had all started to leave as quickly as possible of course so by the time I got to his department the whole building was almost empty. When I arrived he was sat at his desk marking papers and he didn’t look up as I entered.

“Oh yes Ellis thank you for coming. I needed to talk to you.”

He said casually without looking up from his work.

“Yeah about my paper? Is something wrong with it?”

“No, no. I wanted to talk to you about that joke I made earlier. I’m sorry, it was very inappropriate of me.”

This somewhat stunned me, but I managed to stammer something about it being fine.

“No it’s extremely inappropriate of me and some people might have taken it as homophobic. I just want you to understand I have no problem with your sexuality.”

He said, now looking directly at me with quite a serious face.

“I’m not gay!”

I blurted out, perhaps a bit suspiciously. I could feel my whole face burning now.

“No of course not, that’s not what I meant. I just wanted you to know that it’s none of my gaziantep escortlar business but I’m sorry if I caused any offense.”

I was reeling now. How did he know about my urges when it came to men? Was he just guessing or did everyone think this about me?

“It’s okay, I just like having long hair…”

I said, rather lamely. He just nodded and went back to his work. As I walked out of the building I heard a shout behind me and Mr. Phillips appeared out of the doors carrying his briefcase.

“Hold on Ellis, I’ve made you late now the least I can do is give you a lift.”

I was already extremely embarrassed at this point and I wanted to just run home and hide but he was too insistent.

“Nonsense, the next bus isn’t for nearly an hour and I can have you home in no time.”

I relented and we walked over to the staff car park to his large Land Rover. As we got in I felt a change come over him, he stopped joking and there seemed like there was a sort of tension between us, but I wasn’t sure how much of that was simply me projecting all of my confusion and embarrassment onto the situation. As he drove us through the town I realised he wasn’t driving the right way to get back to the area I’d told him I lived in.

“Uh, Mr. Phillips, my house is the other way over to the west.”

I said hesitantly.

“I just need to go home and do something first. Are you okay if we go to mine first?”

He asked me casually but the suggestion was so strange and he gave me a very strange look as he waited for my answer.

“Sure, I guess. It’s not a big town I guess it won’t take very long.”

He smiled a big genuine smile at that and nodded, returning his attention to the road. After a few minutes we pulled into a quiet cul-de-sac in the periphery of the town and he shut off the engine.

“Okay come on in.”

He said, getting out. I stopped and stared at him. I couldn’t read his signals but I felt like this whole situation was already pretty seriously inappropriate. I wasn’t sure how comfortable I was going inside his home and I was really worried that I might think he was trying to make a move on me and end up really embarrassed.

“I think I’ll just stay in the car…”

I mumbled hesitantly as he got out.

“Nonsense Ellis, I can’t leave you here. I’m not really allowed to take students in my car but I wanted to do you a favour. If the neighbours see you out here I might end up in trouble.”

All of this seemed fairly reasonable I was forced to concede, but I couldn’t help but think this whole situation was leading somewhere I didn’t really understand. I followed him into the house, it was a nice big house with plenty of old furniture and antiques everywhere. I didn’t notice any signs of a wife or other family.

“Aren’t you married Mr. Phillips?”

“Not for quite a few years now.”

He laughed heartily. Then he clapped me on the shoulder.

“While we’re here I’ve got something I think you’d like to see. Follow me.”

At this point I was just following behind him as he led me through the house. My now ingrained submissive behaviour started to kick in and I found myself unquestioningly following his lead just as I’d done countless times with men online. I was also becoming more and more certain that this was definitely not above board what we were doing here. At this point he was already in serious trouble if anyone found out that he’d driven me back to his home after college. Even if nothing else happened this was already a huge scandal waiting to happen and I began to worry that I might end up under suspicion that I didn’t need, along with all of the conjecture about my sexuality that the rumour mill would produce if it was discovered that I’d been here. Still as I followed him I was powerless to change my course and couldn’t think of anything to say. We went upstairs.

As we walked into his bedroom I stopped in the doorway and began to protest but he waved away my concerns with a big grin on his face before I could really say anything.

“Just wait right here one moment, you’ll love this I’m sure.”

He patted the bed and God help me I just submissively sat down. He went to the end of the room and disappeared into a door in the corner. I looked around, the bed was a large double and set into the wall opposite of it was a large television. I couldn’t imagine Mr. Phillips being much of a television watcher I’d always imagined him reading a lot of books instead.

In those few minutes while I waited for him to return I had a furious debate with myself. Should I just get up and leave now? What if he really wanted something sexual from me? I definitely wanted it, as we walked through his house I’d really taken stock of him and his body was great. Tall and broad with strong legs and arms and a nice firm manly ass. This could finally be my chance to experience what I’d been practicing each night over the webcam with all those men on Skype. But he was my teacher, it was too dangerous. What if someone found out somehow? No it was best if I just got out of there, I might not have understood his intentions properly anyway. For all I knew he was planning on returning with some old historical relic or something that he wanted me to see for educational purposes. As these thoughts swirled through my mind I heard a door close behind me and turned around to realise it was too late.

He was standing next to the bed wearing only a towel wrapped around his waist, his glorious chest bare and I now realised quite hairy. He was grinning at me and in his hand he held a remote control. I started to back away and stared at him but before I could go anywhere he pressed a button on the remote control and the screen behind started producing loud sexual noises. I turned to see one of the hottest sights of my life. It was a home video of Mr. Phillips on his couch being fellated by a cute young guy dressed in a short skirt and high heels. As the little femboi worked his large shaft, and I now saw it was quite large, Mr. Phillips placed his hands on the boys neck and the back of his head and began to take control, slowly pumping his cock into the willing mouth of his young plaything.

“Oh yes you gorgeous little slut. Suck my cock. You like the taste of that big cock?”

The young guy mumbled something affirmative sounding in between moans through a mouthful of cock. And then removed it from his mouth for a moment so he could talk.

“Oh yes sir I love it.”

He said, licking the shaft from base to head and resuming his efforts. The room was filled with the wet sexual noises of this sloppy blowjob mixing with the low aroused groans of Mr. Phillips and the quiet feminine moans and whimpers coming from the twink that was sucking him off. Hearing him call Mr. Phillips “Sir” had both shocked and aroused me. At college we were encouraged to call all of our teachers “Sir” or “Ma’am” out of respect but here I realised that it could also be a sign of submission, something which I was already becoming quite familiar with. I turned to look at the real Mr. Phillips and he was now sitting on his bed with the towel cast to the side, completely naked and slowly jerking his rather large cock. My mouth fell open, it was even bigger than I’d fantasized it would be and just as thick. He noticed me looking down at it and smiled.

“I told you you’d like to see it.”

He said nodding at the screen.

“Why don’t you come over here and try the real thing?”

I was paralyzed in the doorway, lust and even a bit of fear mixing with embarrassment and confusion. Half of me wanted to walk over to him and sink to my knees and the other half just wanted to run straight out of the house as fast as possible. He seemed to read my mind.

“Nobody else is ever going to know about this. I know you want it. Why don’t you just come over here and feel it?”

He knew exactly what to say and between the sight of this hot older man and his huge cock and the super sexual soundtrack of him being fellated in the background. I was growing more horny by the second. I paused in the doorway for another moment and then I slowly walked over the to the bed.

“What do you want me to do?”

I asked innocently staring with wide eyes into his horny grinning face. He let out a deep satisfied sigh and got to his feet. I felt his large hands on my shoulders and he slowly but firmly pushed me down until I sank to my knees.

“Good boy, get on your knees. I’m going to show you what I like.”

He suddenly slapped my face lightly with his huge cock, I gasped. I’d never actually felt one other than my own and his felt so hard and hot. He laughed and then grabbed the back of my head and pulled my face towards him.

Seeing that large cock rushing towards me I reached out and grasped it, it was the first time I’d ever handled another guy’s cock and it was extremely hard. Strangely it felt different from handling my own. As I started stroking him I heard him exhale deeply.

“Oh yeah that’s good, rub it harder. You ever had one this big?”

I just shook my head no, not wanting him to know how inexperienced I was. He nodded knowingly and put his hand behind my head and started to gently pull my face towards his cock again.

“Stick your tongue out baby. That’s right, lick my shaft from the balls up.”

I did it. Finally after all of those months talking about it and miming it for my horny older guys online I stuck my tongue out and I tasted a cock for the first time. On my knees, legs shaking from lust and exhilaration and still wearing my uniform from the college I started to lick my history teacher’s cock up and down like an ice lolly. Without prompting I held his cock up and started sucking on his balls. He groaned loudly and started to run his fingers through my hair.

“Good boy.”

He growled, suddenly grasping my head firmly in both hands and pressing my face to his crotch. He threw his head back and let out a deep moan. I sucked one of his balls into my mouth and started licking him all over. I realised I was hard as a rock in my tight pants. Looking up at him I saw he was stroking his engorged cock quickly and he looked down into my eyes and gave me a nice big smile.

In the background the sexual noises from the screen had grown louder. It sounded like the Mr. Phillips on the recording was nearing orgasm. The blowjob noises I could hear suddenly became frenzied and I heard him curse and call out on the video.

“Here it comes, OH FUCK! Oh fuck yeah, swallow it all you sexy little bitch!”

The young crossdresser from the video started making muffled moans while I continued to lick and suck on his balls and he ran his hands through my long hair. It was by far the most erotic experience of my young life. The sound cut out as the video ended and suddenly the room was silent except from Mr. Phillips moans as he enjoyed the very real oral attention I was paying to him in the present.

“You liked my video didn’t you? Did you like the ending?”

I started to nod and he quickly reached down and grabbed my chin, pulling my face up into his. Before I even had a chance to react he was passionately kissing me on the lips. I gasped and his tongue entered my mouth immediately, I felt myself melt into him. His strong arms lifted me up and onto the bed while his hands began firmly kneading my ass, it felt incredible. I pulled away from him from a moment panting in excitement and smiled up into his handsome bearded face.

“Okay stand up for me, show me your sexy body.”

Still reeling from that incredible kiss, I clumsily stumbled to my feet in front of him. I began tearing my clothes off while he slowly wanked his huge dick and looked me up and down. I threw my jumper and shirt to the floor and started to undo my trousers but he stopped me.

“Turn around and show me your ass.”

He commanded. I spun around and bent forward a bit, knowing that it would drive him wild. I bent forward and started gyrating my hips as I slowly pulled my pants down and revealed my bare ass to him. Then I was standing fully naked in front of him, I bent forward and started shaking my ass to tease him a little. Smack! I jumped and gave an involuntary little shriek as I felt his large hand slap my ass. Suddenly he surged to his feet and wrapped his arms around me from behind pinning me in place bent over in front of him.

“I’m going to fuck your pretty little brains out.”

He whispered into my ear, biting my neck lightly and sending shivers through me. I was so horny my body was buzzing but the thought of having that large cock forced inside of me gave me an edge of fear and I panickedly struggled against his firm grip.

“No! Wait!”

I implored, trying to turn my face to look at him. He responded by spinning me around and collapsing both of us onto the bed, his hulking frame crashing down over my skinny bound form and forcing a moan out of me. I could feel his cock, now hard as a piece of steel, pressed between my ass cheeks. He started to rub it up and down, the tip poking the small of my back as he grunted. I was pinned to the bed by his huge naked body as he pleasured himself against my soft ass cheeks. He licked my neck then started nibbling on my ear as he humped me. The aggressive thrusts and his heavy horny breathing in my ear were driving me wild.

“Don’t be a tease I know you want it.”

He said gruffly in my ear whilst still grunting and rubbing himself hard against my ass cheeks. He released me for a moment and I collapsed to the bed, he turned around a retrieved a jar of lube from the bed side table. Now I definitely wanted what he wanted to do to me, I’d been fantasizing about it for months. And yet it was all moving so quickly and I was afraid he was just going to just start fucking me like crazy and hurt me due to his size and my inexperience.

“Wait Mr. Phillips! Sir! Please, I’ve never done it before…”

I timidly trailed off. He turned slowly with a look of genuine surprise on his face and then he grinned.

“Oh you still haven’t had your cherry popped! I’m sorry Ellis when you started doing that slutty dance for me I thought you were a lot more experienced, I must have startled you pouncing on you like that.”

He laughed goodnaturedly and I started laughing with him.

“Well the truth is Sir that I’ve fantasized about it a lot but I’ve never even met a guy in real life.”

I finally admitted. At this his smile grew even wider and he drew me in to him with one arm and started groping my ass with the other. He grabbed one of my hands and brought it down to his still rigid cock, he began to slowly rub himself with my hand and I took the hint and started wanking him myself. He suddenly gripped my face in one large hand and pulled me intimately close to his own.

“So you’ve never even sucked a man off before?”

He asked earnestly, staring deeply into my eyes. I just shook my head slightly and gasped, his other hand down behind me stopped groping and started teasing my asshole. He pulled my face in for another long kiss, I moaned softly as he ran his tongue into my willing mouth. I tightened my grip on his cock and started jerking it wildly as he groped my ass and his fingers teased my asshole. Suddenly he broke the kiss off and grasped me firmly by the throat staring intensely into my eyes.

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