Author’s Note: I changed names in this story for anonymity. Obviously not every quote in this is verbatim. Like most people, my memory’s not perfect. That said, this is how I recall it going, more or less. This is my first post here, I hope you enjoy the read!
So, before I begin this story, let me tell you a little bit about myself. I’m Ramona, a 22 year trans girl in my sophomore year of college (I’ve taken a gap year, switched my major recently, and I’m hopefully transferring to Georgetown soon). I’m 5’10”, with long, thick, wavy blonde hair and grey eyes. I have sharp features, with very high cheekbones, a straight, thin nose, etc. I’m quite pale; I’m religious about using sunscreen. I’m thin, and weigh around 125 pounds. I have what could be described as a bottom heavy figure for my weight. My boobs are on the smaller end of a C cup, and I have moderately wide hips, a bit of a bubble butt, and thighs to match since I work out a fair amount.
This story actually took place during the summer before my freshman year of college, when I was 19. For most of the summer I had been hooking up with a girl named Autumn. I had actually lost my virginity to her pre-transition too. So you know what she looks like, I’ll describe her here. Autumn is very tall, around 6’0”. She has slightly tanned skin, blue eyes, and she’s constantly dying her hair different colors, usually pink or purple. She has gentle cherubic features and a button nose. She has curves for days; she’s quite busty and has wide hips and a very big butt.
Autumn is a year older than me but we both stayed with our moms during the summer and lived on the same street. Since our moms were often on business trips, we usually had one of the houses to ourselves.
Sometimes she and I would just hang out and watch TV or play video games together, and other times we’d sleep together. It was relatively casual. Usually, she took the lead. I’m pretty shy and submissive to begin with and Autumn’s the polar opposite. We tried all sorts of things, but most of the time, she’d finger me and give me head, ride me until she came, or sit on my face while I ate her out. It was fun, and I wasn’t going to complain that a gorgeous woman wanted to sleep with me. One day though, we were lying in her bed and cuddling after sex when she asked if I’d be up for doing kinkier stuff.
I didn’t know how to respond, she was one of the only people I’d ever slept with at the time. I asked, “Um, I guess, but what did you have in mind?”
“You know, handcuffs, spanking you, that sort of thing.”
I blushed and stuttered out, “O-oh, yeah, I mean, if you want to do that.”
She smiled and said, “Good, next time. It’ll be fun.”
I wasn’t entirely sure what it’d be like until the next time I saw her. I went to her house the next Saturday, and we got Chipotle, chilled out for a bit, and then we started making out. One thing led to another and we went to her bedroom.
“Get undressed, lie down, and close your eyes,” she told me. “I’ll be back in a second.”
I did as she said, and anxiously waited for her. I could hear her open up her closet and pull something out, but I wasn’t really sure what it was. Then I heard jingling and had a pretty solid guess. She came back over, and said “Open your eyes, Ramona.”
I opened them, and she had handcuffs in one of her hands, and a buttplug in the other. I gulped and said, “Are we going to use those?”
She laughed. “Obviously! Could you put your hands up and spread your arms apart?”
I did as she asked, and she handcuffed me to her bedframe.
“Let me grab the lube,” she said, taking a bottle from her bedside table. “I’ll be gentle.”
Now, anal play wasn’t exactly new to me. As a pre-op trans woman, it was and still is a welcome part of my sex life. At the time, I’d fingered myself and used a vibrator on myself before, and Autumn had fingered me too. Still, this would be a little different. Being handcuffed, I wouldn’t have any control.
“Don’t worry,” Autumn said gently. “I’m not stupid, I did a little research. We’ll set up a safe word if you want this to stop at any time. Most people online recommended green for a ‘good’ signal, yellow for ‘slow down’, and red for ‘stop’. Does that work?”
I nodded shyly.
“Hey, come on,” Autumn said with a smirk. “Use your words, doll.”
“Yes,” I murmured.
“There we go.”
She opened the bottle of lube and put some on her fingers before lying down over top of me, lowering her fingers to my asshole, and slowly penetrating me. “Just to loosen you up,” she whispered in my ear, before nibbling on my earlobe and trailing kisses and bites down my neck.
I bit my lip in an attempt to hold back my moans, but Autumn quickly noticed. “Tsk, don’t hold back. I want to hear all those pretty noises.”
She took her fingers out of me and I let out a whine at the empty sensation. She laughed. “Hey, it’s alright, you won’t be empty for long.” She was covering the buttplug in lube, and shortly after, put it in me as softly as possible. I moaned as it penetrated me. “Such a beautiful girl. Alright, now it’s my turn to feel good.”
She stripped down, got a condom from her bedside table, and put it on me. Then she straddled me, and began to ride me. She felt incredible, and between her riding me and the anal stimulation I was losing my mind. After about 5 minutes, she came, and I was about to too.
“I’m close!” I said. Immediately, Autumn pulled herself off of me.
“Ah, ah,” she said. “You’re not cumming today.”
“Why not?” I whined.
“Because,” she said, “you’ll cum when I let you.”
“B-but! That’s not fair!”
She slapped my thigh harshly, and moved up toward my neck, biting it hard enough to bleed, and sucking, leaving what was sure to become a dark purple hickey. “Bad girl!” she scolded. “I’m in charge, right?”
I reluctantly nodded.
“Alright. You’re not going to cum until you see me again, do you understand?”
“What?! No way-“
Autumn slapped my thigh again and grasped my jaw roughly. “Open your mouth,” she ordered.
I did, and she immediately spit in my mouth. “Swallow,” she said.
I swallowed and she asked “Who’s in charge?”
“You are,” I sighed.
“There we go. Now you’re listening. I promise I’ll make it worth it next time you see me. It’ll be your reward.”
“Fine,” I grumbled, rolling my eyes.
“Watch the attitude. I don’t want to have to punish you.”
“Okay…”
I spent another few hours at Autumn’s place. She got me some water and Skittles, I took a short nap, and watched a couple episodes of Bob’s Burger’s before leaving.
“I’ll see you soon,” she told me.
Thankfully it was only three days before I saw Autumn again. It stunned me how quickly she’d taken control the last time I saw her. I had no clue what she had planned this time, but I couldn’t deny that I’d had fun before.
I went to her house and when she let me in, the first thing she asked was, “Did you follow my rules?”
“Yes,” I muttered grumpily.
She chuckled. “It’ll all be worth it today, okay?”
“You said that last time. What’s going to happen?”
“I’m going to tie you up and fuck you,” she said casually. “With a strapon.”
I felt like my brain had short circuited. “Uh…but…wait, I’ve never-“
“Been on the recieving end? Cute. I’ll be your first time again then, huh?”
“I guess…”
Autumn furrowed her brows in concern. “We don’t have to do it if you don’t want, you know? It was a little pricey to buy the stuff but I haven’t used it so I can return it. I don’t wanna’ do anything you’re not okay with.”
I blushed and smiled at how kind she was being. I didn’t want to let her down but I was definitely nervous. “Maybe we can just take it slow? And chill out first? Before we do anything?”
She nodded. “Whatever you’re comfortable with.”
After a couple hours of relaxing, I’d finally worked up the courage to do what she wanted. “I’m ready,” I said shyly.
She grinned. “Great! Go to my room, strip, and lie face up on the bed.”
In Autumn’s room, she took out some silky looking rope and a strapon that was luckily smaller than I expected. She put on the strapon and then she started wrapping the rope around my calves and shins, before tying the lower half of my legs together. “It’s a pretty simple tie,” she said. “I didn’t have time to learn the more complicated ones online. I’m new to it though, so let me know if it’s too tight or something seems wrong.” She rolled me onto my back and tied my arms together. Finally, she manuevered my tied legs so I was in a face down ass up position. “Are you comfortable enough?” she asked.
I nodded slowly.
She spanked me lightly, and scolded, “Words, sweetheart.”
“Yes, I’m comfy,” I said.
“Good. Fuck, you have a nice ass.” She grabbed my ass with her palms, spanked me again, and spread my cheeks before spitting into my asshole. I gasped in shock at the sensation. I heard her open a bottle, and shortly after I felt her lube covered fingers inside me. She started with one, but before long upped it to two, and then three. She kept making a come hither motion in just the right spot and before long I was moaning like a bitch in heat. “I want to write some stuff on you,” she said. “Give me a sec, there’s a Sharpie on my desk.”
“Okay,” I said quietly. After a moment Autumn had come back over and I could feel the cold tip of the Sharpie writing on my ass. I figured she was putting some degrading phrases like ‘slut’, ‘whore’, and ‘bitch’ on me but thought nothing of it.
She kept fingering me for a while longer and added a little more lube before she finally decided it was time. “I think you’re ready,” she said. I braced myself and felt her strapon enter me.
I moaned and whimpered a little, while she rubbed comforting circles on my lower back. “It’s alright,” she said. “We’ll take it slow, let me know when I can speed up.”
For about five minutes, she rolled her hips at a torturously slow pace, but I wasn’t sure if I was ready. After a while though, the anticipation became too much to bear. “You can…you can speed up.”
“Great!” she exclaimed in excitement. She only sped up a little but it felt so much better, with the tip of her strapon pressing against my prostate over and over.
“Faster!” I moaned.
“Alright!” she said, and she set a brutally fast pace.
Before long, I was about to cum. “Please,” I begged, “I’m about to cum, can I?”
“Of course darling! This is your reward for being a good girl on Saturday, cum as much as you want.”
My first orgasm rolled over me, but Autumn didn’t stop thrusting her hips. “Good slut!” she exclaimed. “Cum for me.” She started spanking me roughly, and I was sure it’d hurt to sit tomorrow but I didn’t care. Getting fucked felt so damn good.
After the first time I came I kept cumming over and over, but it was clear that Autumn wasn’t going to stop until she thought I’d had enough. After about half an hour, it was too much. “Re-red…” I sputtered out.
“Oh!” Autumn said, and she stopped immediately. “Sorry Ramona…I got a little too rough there, didn’t I?”
I shook my head no. “No…it-it was good, just a lot…”
“Alright,” she said. “Well just give me a sec to take this out.” She gently removed her strapon and I crumpled onto the bed. “Are you okay?” she said softly. “Let me untie you.”
“I’m fine,” I said sleepily. “Just tired…”
She finished untying me and said, “Well, let’s get you some food and water and get you cleaned up. First though, let me show you what I wrote on you.” She grabbed her phone from the bedside table and took a photo of my ass, before showing it to me. My butt was red and a little bruised, but the Sharpie was still legible. She’d written compliments all over me, ranging from ‘smart girl’ to ‘beautiful’ to ‘perfect’.
“You’re sweet,” I mumbled.
“I’m glad you think so,” she said. She picked me up bridal style and sat me on the edge of the bathtub before running a bath. “I’m going to order a pizza and change the sheets, what topping do you want?”
“Sausage please.”
“Alright, I’ll be right back,” she said.
“You can stay the night,” she told me. After my bath she made me drink some water and the pizza arrived. We watched Spirited Away and The Lost Boys before going to her bed.
She whispered in my ear as we spooned, “You were so good. Did you have a good time?”
“Yeah,” I said. “We should keep doing this sort of thing.”
“Sounds like a plan,” she said, and we both drifted off to sleep.
Over the past few years during the summers I’ve kept up my friends with benefits arrangement with Autumn. It could never work as a real relationship because of distance but she’s a great friend and lover. She’s in France until the 4th of July, but I’m excited to see her this summer.
[link] [comments]
from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/vofjwx/my_summertime_friend_with_benefits_ff_tf/
Comments
Post a Comment