My year as an escort, and the time my best friend was a customer [FM] [Cheating]

*The events here happened six years ago. My memory isn’t perfect, but many of these experiences are burned into my brain. I look back on it with some yearning, and some embarassment. It was an interesting time in my life, and I would be lying if I said I didn’t enjoy some of it. I may be filling in the details here and there, and names are omitted.*

My parents spoiled me relentlessly growing up. By the time I was a college student three years into my Literature degree, I had never worked for a single penny in my life. I was entirely dependent on my parents’ financial support, so it was devastating when during one winter break, they found pictures of me posing naked, handcuffed to a bedframe that I had taken for my FWB on my phone. Their image of their good little girl was shattered.

Them confronting me on it led to a much bigger argument, where years of my pent up frustration slipped out. Their deeply Christian views had been at odds with my hedonistic view of the world for a long time, and I was pretty sick of their constant judging and pretending to care during church visits. I let slip that not only had I been deviant enough to sleep with boys outside of holy matrimony, that I’d even tried weed (the devil’s lettuce), drank with friends every weekend, and had even gotten to third base with another girl. My mother nearly fainted, and my father was at a loss for words as he realized where the money he’d been sending me for “tutoring lessons” had actually gone.

Though I definitely should have seen this coming, I was still caught off guard when they canceled my credit cards and told me I’d be completely on my own financially thereafter. So there I was, dropped off at the curb of my apartment, with twenty bucks in my wallet, and a year of tuition, housing, and food to pay for. I had never stepped foot inside a bank, much less taken out a student loan. I had no idea what to do.

In a move I would later come to regret, I decided to move in with my FWB, as I could no longer afford the rent at my luxury apartment. He let me stay with him free of charge, and I thanked him by having him fuck the stress out of me every night. I sent him a picture with my hands just barely covering my boobs and my pussy as he commuted home from work, and ask him what he wanted me to wear. It didn’t matter much, because as soon he got home, he’d rip it right off me and pin me against the wall. I swear, it must’ve been an average of 4 or 5 seconds between him coming through the door and him entering me. It helped that I’d be dripping in anticipation. I didn’t have much to do those days, besides stress out about my life, watch porn and shitty movies, and think about him coming home.

I contacted the school and told them I’d be taking a semester off, with a bullshit story about how I wanted to take some time to work on my mental health issues. When I hung up the phone, I buried my face in my lap and cried like I never have before. The fact that I was actually doing well in school and loved what I was studying had been one of the few things I was proud of in my fucked up life. A few hours and a box of tissues later, I picked up the phone again and called my best friend – let’s call him Ben.

Ben was probably the only person I could really confide everything in. We met in a freshman writing class, where we shared notes whenever one of us missed class. Well – I say we shared, but really it was almost always him sharing his notes with me. I remember being so impressed by his handwriting that I secretly took a few pictures of his notes. Since that class, we’d been inseperable. Boyfriends and girlfriends came and gone, but we were always there for each other.

In a shaky voice, I asked if he could meet up for drinks tonight. He already had dinner plans with his girlfriend, but asked if I was okay. I started sobbing again, and replied “no” after a few seconds.

“Where are you? I’ll come get you.”

He may not have known it then, but those words, spoken in his husky British accent, were exactly what I needed to hear at that moment.

An hour later, we were sitting down at our favorite coffeeshop. I unloaded everything on him as he listened intently, and at the end he gave me a deep bear hug, telling me everything would be okay. My chest pressed into his, so closey that I could feel his heartbeat through his shirt, and smell the faint cologne from his neck. I also felt a growing stiffness below his belt, pushing against the thin fabric of my yoga pants. For a moment, I wondered if he saw me as more than a friend. I swept the thought aside, because he was a guy in his early twenties pressed tightly against a girl with a nice rack and a bubble butt, so who could blame him? Not to mention he was in his first relationship that had made it to the six month mark, and I wanted to be invited to the wedding.

That night I shaved my pussy completely bare, wore nothing but black socks, sprayed a bit of whipped cream on my tits, and sat in a chair in front of the door. When my FWB came home and saw me, he went slack jawed and just stood there staring at me. I made a come hither motion with my fingers, and he wasted no time picking me up, sprinting to the bedroom and dropping me on the bed. I grabbed his hair, and pushed his head to my nipples, where he began licking off the whipped cream. The tingling sensation combined with the warmth of his mouth sent shock waves through my body, and I felt myself getting wet. I pushed his head further down, until his face was buried in my crotch. Wrapping my legs around his neck, I clamped down, forcing his face into my pussy.

He began working away with his tongue on my clit, licking relentlessly while working the edges of my labia with one finger. Waves of pleasure rolled through my body, and I felt like my mind was going blank.

“Yea baby.” I said. “Show me how much you missed me.” I knew he loved the dirty talk, and I had all day to think of lines to get him going. He responded vigorously, pushing his one finger deep inside me, while continuing to suck and lick at my clit like he’d been starving for days. Once inside, his finger repeated the “come hither” motion I’d made to him earlier, pushing against the upper walls of my vagina. I felt it building up inside me, and lost partial control of my body as my back arched and I came all over his finger and his face.

My FWB was a former frat boy who worked out six days a week, ate a diet of exclusively spinach and chicken salads, protein shakes, and alcohol. I met him one day at a Halloween party where I was going as Daenarys with a white wig and he happened to be a very lazy, shirtless Jon Snow. He introduced himself with a pickup line that was somehow related to Game of Thrones, and one drunken hookup later he still remembered my name in his phone. We continued to fuck on and off during my third year, progressively getting kinkier until the pivotal picture of me tied to the bedframe that had gotten me disowned. He was fun – a lot of fun, but not someone I’d get serious about.

“That’s how much I missed you.” He said, grinning. Then he got up off the bed, grabbed a fistful of my hair and half dragged me to the floor, pushing me on my knees.

“Open up.” He demanded, and I happily obliged. A moment later, I was tasting my own juices on his cock. It wasn’t really my thing, but I knew it was a fetish of his, and hey – free rent is free rent.

“Mm daddy, you taste so good.” I said as I throated his member. His dick was average length, but fairly thick, so it was a bit hard to take all at once. He grabbed the back of my head, and then I knew what was coming, so I took a deep breath. He began thrusting vigorously, his member sliding deep into the back of my throat. With one hand on my neck, so he could feel himself moving as he continued to face fuck me mercilessly. Reflecting on our sex now, he fucked me back then with a roughness that could be described as brutal, but there was no question that I loved it. Because that’s what I wanted. Because that’s what I deserved.

Finally he gave me a chance to breath, and I gasped, choking for air. He put a finger in my mouth, playfully caressing my tongue.

“You like that, you little slut?” He said.

“Yes daddy.” I whimpered through heaving breath. I ran one hand down his abdominen, softly caressing his abs. As my hand slid further down, it wrapped around the base of his cock, and I positioned myself below his dick subserviently. My tongue traced the base of his shaft towards the head, and I licked the spot connecting his bulb to the rest of his cock. He shuddered in pleasure, so I repeated the action, going from the base to head, stopping to spend some extra time with my tongue on his head. I jerked him off in a twisting motion with one hand, while the other found its way to my still dripping pussy to begin play with myself.

He closed his eyes and began to quietly enjoy my service. He gently played with my hair, which at the time was soft and black and fell down to my waist. This went on for a few minutes, as I kneeled licking his rod, getting increasingly wet and anxiously hoping that he would fuck me at some point. He didn’t disappoint, as he abruptly lifted me up onto the bed, and pushed my legs into a spread eagle position. He grabbed his cock and rubbed the head against the entrance of my pussy, up and down as he looked at me with a mischievous grin. He continued doing this until I felt like I was going to lose it, then suddenly he entered me. With deep strokes, he pounded away as he pushed my face into the pillow. For the next few minutes, I screamed so loud that I thought the neighbors might file a noise complaint.

Then he leaned over and picked me up again, forcing me into a sitting position as he laid down on the bed. He slapped my forcefully and said “giddy up”. I began to bounce on his cock, pushing my butt cheeks against his legs with each stroke. With a moan, he grabbed a handful of my ass and squeezed. I rode him harder and harder, as he continued to repeatedly slap my butt and squeeze my cheeks, until I felt him growing bigger inside me.

I was dumb about many things back then, but I was smart enough to track my ovulation cycles. So I leaned down into his ear and whispered for him to cum inside me. And so he did, in warm spurts that filled me up inside and continued to leak onto my thighs and all over the sheets after I got off of him and went to clean up.

We cuddled in the post-coital glow on his bed, our naked bodies pressed against one another for warmth in the DC winter, and we laughed about how silly I felt spraying whipped cream on my boobs. The part I left out was how I’d heard about it from a conversation with Ben’s girlfriend, that he loved licking stuff like whipped cream off her body.

Changing subjects, I asked my FWB how work was, and he replied that it was fine. Then he asked how my day was, which was unusual as he rarely asked much about me. I said shitty as usual, and to my continued surprise, he asked why with a hint of genuine concern in his voice.

“Well it’s just that I’m a broke college drop out and my parents disowned me, and I have no idea what I’m doing or what I should do.” I said, opening up to him for the first time in our almost entirely sexual relationship. “But than that, I’m swell.”

He looked at me in a way that seemed like he was both sympathyzing with me, but also think deeply about something else.

“It’s alright. Don’t worry about me.” I said, with a peck on his cheek. “I’m just a bit of a mess.”

He grabbed ny hand, and looked at me with a sudden intensity. Like there was something he really wanted to say. For a moment, I thought that he was about to confess his love for me – which would have been pretty serious complication for me. But the words that came out of his mouth next were even more surprising.

“Have you ever considered escorting?” He asked.

I gaped at him, searching his face for clues that he was joking. His expression was dead serious, with a hint of nervousness. Like he was worried I might slap him.

“Are you serious?” I said with a nervous laugh. “So that’s what you think of me?”

He shook his head. “A buddy of mine is into it. You need money, don’t you? He says he pays them between $300 or $400 an hour. And he’s shown me pictures – trust me, they’re not as hot as you.” He runs his hand down my back, continuing to gaze intensely into my eyes. “You could probably make even more.”

I was taken aback. Admittedly, the amount of money surprised me. I’d done the math, and I would need about $45,000 to finish school. Working at a minimum wage job, it would take years to save that much. A loan was probably out of the question, with no parents to co-sign.

“They really make that much?” I asked hesitantly.

“Absolutely.” My FWB flipped open his laptop and pulled out a website with pictures of tons of girls. He clicked through them, and showed me the rates. They all asked for “Donations” or “Roses”, ranging from 300 to thousands. I couldn’t believe it.

“Those girls are really hot though.” I said.

He shook his head. “A lot of these pictures are shopped, or just straight up fake.” He leaned in close, placing a hand over my breasts and caressing them. “I bet we could take a few of you that look way hotter.”

I’ll cut the long story short here. It took some convincing, and some examining of how my future self would feel, but the money was too good to pass up. My FWB helped me set up a page, with a few pictures that we edited with some filtering, and even a nice video of me in the shower pressing my chest against the glass. We put black bars over my eyes, and posted the listing on a few sites.

At first, there weren’t many bites. I figured either my pictures weren’t good enough to compete with all the women with perfect bodies – photoshopped or not – or there just wasn’t anyone still paying for sex. So when I did get the first text on the burner number we set up, I was actually excited.

We met in a hotel room he booked. I followed his instructions, and went up to the fourth floor, and knocked on his door. A portly, middle aged man in a dress shirt was behind the door. I smiled and shook his hand, hoping he couldn’t feel the nervous sweat on my palms.

There was a wad of cash on the table. I picked up the bills and sifted through them. Four hundred dollars. That was the price of my body, for an hour. Honestly, not bad.

His arms wrapped around me from behind, and he began to grope at my chest. I responded with as much enthusiasm as I could muster, sliding my hand down to his pants and feeling for the stiffness. I didn’t find it. I turned to face him, to position my hand better, but was met with a full blown kiss. His tongue sought out mine, and I tasted the musky cigarettes in his mouth. Then slowly, I felt his cock hardening against my hand, and I began to stroke it gently.

He began to undress me, fumbling a bit with my bra under my shirt. I had asked him over text if he wanted me to wear anything
in particular, and he said whatever I was comfortable in. So I showed up in a t shirt and jeans, which was now coming off and lying strewn on the hotel floor.

He gently led me over to the bed, and laid me down. He undressed, and I could see his cock was now standing at half mast. I took it in my hands, and began to stroke gently.

“Is that good?” I said as I stroked him, and I felt him rising more as I continued.

“Yea. Really good.” He said, as he fondled my boobs. “You got the wrapper?”

I looked at him. He was asking me if I had a condom?

“No, don’t you have one?” I asked, confused.

“No, the girls usually have one.” He frowned. I cringed. I was showing how green I was.

“Let me check if they have any in the room.” He fumbled around, his dress pants around his ankles, looking in the hotel drawers. After a few seconds of searching, he triumphantly held up a colorful condom. I smiled at him, and beckoned him to come back to bed. Hopefully, I could still salvage the session.

My FWB had impressed on me how important it was to get good reviews. “Imagine you’re a restaurant on Yelp.” He said. “Your first few reviews are really important.”

Peeling the condom back, I gently pushed it around his cock, now at full attention. Then I gave the tip a small peck, and laid myself out on the bed, spreading my legs and gesturing him to join me.

He wasted no time entering me, and began to pump. His rhythm was shaky, and he was heaving with effort. I gently ran my hands down his chest, feeling myself beginning to get aroused as he fucked me. It wasn’t exactly like sex with my FWB, but that didn’t pay $400.

Then he suddenly heaved heavily, like he was sighing with relief. I blinked. Was it already over?

He rolled over on his back, the condom filled with him cum hanging off his deflating penis. I turned around and wrapped my arm around his chest, giving him a kiss on the cheek. That wasn’t so bad.

My first few customers went by in haze, the sessions melding together in my memory. There were many middle aged men like the first one, and many that came quickly. I imagined that their sex lives at home weren’t exactly vibrant, and sleeping with a young woman who at least seemed pretended to be into them got them off fairly quickly. Some of them talked to me, telling me about their jobs, their lives, their kids, and I listened.

Soon the cash started to pile up, and I paid a freelancer to help me make a website, and another photographer to take better pictures of me. A few customers became regulars, that I got to know on a first name basis – although they never learned my real name.

And so, as I settled into the life of a full time escort, I found the first thing that I couldn’t tell Ben about. Ben, the friend who I told everything. I wasn’t sure if it was shame, or that it just be awkward. I knew Ben wouldn’t judge me, but he would be concerned about safety, and at the time I was not ready to have the conversation with him.

Meanwhile, my FWB was cheering me on, and had pushed me to get into this. He seemed genuinely happy that I was doing better, and had something to keep myself occupied with a goal in mind. For some time, my affection for him started to grow, and there was a voice in the back of my head that wondered if we could be more than hook-up buddies. Though we became better friends, our sex life suffered, as I was too exhausted and sore to really get him going. I started to pay him rent, because it was only fair, though he didn’t want to take it.

One day, I got a text from a new customer. After a brief chat and some background information, we agreed to the typical procedure. We would meet in a hotel room in downtown, for $400 an hour. The only thing out of the ordinary was that he said he was 28, which was fairly young, but I didn’t think much of it. Maybe he would be someone I could actually imagine being into naturally, for once.

I approached the door on the 3rd floor, and knocked. The only specification the client had made was for me to show up in yoga pants, so I was waiting there in my Lululemons patiently waiting for the door to open.

When it finally did, I gazed into an empty hotel room, totally untouched by the presence of a human.

“Could you show your face, baby?” I asked sweetly. Maybe he was a bit shy, but I needed to verify that they were who they said. If they looked way too old to be 28, I would bail. For a moment, there was no response, and I reached for the mace in my handbag, clutching it tightly.

Then he took a step past from behind the door. “Sorry, just a bit new to this.” The voice was a smooth husky sound, with a beautiful British accent. It took everything in me to stop from yelling out when my best friend Ben stepped out from behind the door. His eyes flickered with recognition, then with horror of realizing that his best friend was the escort he had ordered.

This went on longer than I expected. It’s getting very late, but I will continue some other time if there’s interest. Thanks for reading so far!

Source: reddit.com/r/gonewildstories/comments/adhjyt/my_year_as_an_escort_and_the_time_my_best_friend