Grew up in a pretty standard household. As “normal” a family you get out there. Parents who were keen on instilling religious values. It all seemed standard. The religion naturally led to internalised shame about sex and being a sexual person. I also think I had an awakening much after my friends as they talked about these things often and I found myself not being able to relate.

After college, couple of toxic boyfriends later, is when I truly started feeling sexually liberated. Still cautious, self-conscious but internally very aware of what I liked and wanted. And it was undoubtedly affection and attention from older men. Jobless and with an uncertain future, I was going through a lot of stress. The only thing that helped me fall asleep was touching myself between my legs, over my panties thinking about middle aged men sleeping with me while leaving their boring wives at home.

I moved back home for a bit. After many crying sessions and mini breakdowns, one option that my father thought for me was setting up a coffee chat with one of his friends. He was like, “listen, I know there’s not a lot you’re interested in right now. But just talk to Doug. You know Doug. And I’ve seen the kind of mentorship he provides to many bright young individuals and they’ve all gone on to do really well for themselves. Plus, you know he’s Doug. He’s not going to lecture you the same way you think I do and I imagine you won’t have these outsized reactions to what he has to say.”

I agreed. I actually did like Doug. I went for the coffee with him with as innocent of a mindset a perpetually horny 26 year old who didn’t get fucked enough in real life can. It actually was a fun, candid conversation and I left feeling like I had a bit more direction in life. We followed up on these chats and Doug being the man he is, ensured every interaction was also an enjoyable one. He took me out on nice dinners and lunches by the sea, drinks at expensive bars. He encouraged me to loosen up a bit and was showing me how to enjoy life without spelling it out in those words. I don’t even know if I’d call what I felt towards him a crush or not. I just knew I had started to grow a deep affection for his companionship and guidance. I knew I wanted to please him and make him proud.

My parents were having some friends over one night and I hung out with them as well. I had a glass of wine and played board games with Doug and some of my parents’ other friends including Doug’s wife. She left pretty early after a game, complaining of a headache. I also went up to my room after a bit, letting the older people hang out. Close to midnight, I heard the noises downstairs go away and figured everyone had left and my parents had retired for the night (they lived in a completely separate part of the house than where my room was). Only a few minutes later, I heard a knock on my door and saw Doug poking his head through.

“Oh good, I thought you might be awake. The night owl you are.”

I was lying stomach down on my bed, on my laptop, wearing my sleeping outfit which consisted of a light blue tank top and white cotton panties with little hearts on them (that he couldn’t see because I was half underneath my blanket. I knew though that my cleavage was on full display for him and maybe even my nipples were poking through.

He came into my room without invitation and looked around. “I was almost out the door but thought I’d come by and say goodnight to you. You left early.”

“Yeah what was I going to do there with all of you middle aged men? I figured you didn’t want me hanging around, ruining the vibe.”

“Oh baby one thing you should know, middle aged men always love having a pretty young thing like you around.”

“How drunk are you Doug? Besides, I don’t know if the same applies for the wives of those men.”

“I am just a little buzzed. And who cares about the wives. They always find some reason or the other to be upset. By the way, nice room. Very pink. Very girly.”

“Yeah I haven’t changed it since I was in high school.”

“You should keep it like this. It suits you.” He paused and stared at me for a bit and I could see, no I could feel, the heavy weight of his gaze on my cleavage which hardened my nipples. If he couldn't see that before, he definitely could now. He let out a heavy breath.

“Well I am here to say good night. Good night. Let me come give you a hug.”

He came over to me, sitting down next to me on the bed and I lifted myself into a half seated position so that he could hug me easily. He wrapped his arms around me tight and buried his face in my neck, sighing deeply. He started stroking my hair and my back and he let out another deep breath.

“You’re a tease, aren’t you.”

“You’re the one who came into my room, Doug.”

“But you’ve been teasing me this whole time. Wearing those tight tops and short dresses. I kept thinking you would turn to me for more than something professional. I know you needed emotional release and I tried to make myself so accessible to you. But you never did.” While saying all these things, he started moving against me as his hands continued exploring my arms, back and legs.

“Oh Doug, I didn’t think you would appreciate that. Are you like this with all your mentees?”

“No, just you babygirl. I have had a crush on you for longer than I can admit.”

This sent a rush through my entire body and I could immediately feel myself ooze out wetness between my legs. At this point we were passionately cuddling with our legs wrapped around each other, both of us rubbing frustratedly on each other. Doug lifted my leg and wrapped it around his hip and thrusted into me, making me feel his hard on. It felt so good to feel his cock against my wet panties and again I felt a rush of thrill at being able to produce this effect in him. He cupped my face and looked into my eyes as he humped me. “A really good goodnight cuddle for my baby girl.”

He then finally brought his lips to mine and started kissing me softly, making me moan in pleasure and I soon opened my mouth to be able to kiss him more deeply. It was a lot of kissing and sucking on each other's lips. Kissing an older man felt different. There was a lot of tongue. A lot of him sticking his tongue out and using it to flick mine. We continued this for a long time as his hands alternated between being under my shirt and cupping my tit and rubbing my pussy with his four fingers, making me sopping wet. Eventually he unzipped his pants, lifted his girthy medium sized cock out which was already slippery wet, pushed my panties to the side and slid it inside me with a grunt. He held it inside me and let out a deep moan into my ear. “Ah fuck. Fucking hell babygirl.” He held on to me extremely tightly as he fucked me, so much that I had trouble breathing but I had never felt so pleasured. He kept thrusting into me deeper and harder. “You’re so young. You’re so beautiful. Oh fuck you’re pussy feels so tight. I am not gonna last long. Fuck, I need to unload in you so badly.” This is when he really picked up the pace and I felt dirtier and more used than I ever had in my life, as he shot ropes of cum into my pussy and pulled my hair and stifled his moans and grunts in the side of my face.

After cleaning ourselves up, we decided we would fall asleep together and he would set an alarm for 5 am. At which point he would wake up and go sleep on the couch and the story would be that he had been too drunk to drive him, a completely normal occurrence.

We made out some more and fell asleep with him spooning me and one hand firmly placed on my breast. I was woken up a few hours later, feeling confused. I was on my stomach and I could feel Doug’s weight on top of me. That’s when I realized what was happening as I could feel that Doug was hard again. He only slightly lifted my hips up, positioning his cock so that he could stuff it into my pussy. Once he was in, he allowed me to feel the full weight of his body as he fucked me like that. It was painful but I was also immediately turned on and felt like all my dreams were being answered in one night. He grunted heavily, and used one of his arms to push my face deeper into my pillow while he kept fucking me. He was shaking all over as he came inside me but he pulled out and made a mess on my ass and back. “You fucking whore” he whispered as he spilled the last drop of his cum on me. Using my discarded panties that lay to the side, he wiped his cock clean and got out of bed. I heard him get dressed and leave my room without saying a word to me.