I Was Determined To Prove Myself

I had known Claire since college. She moved into her career as an accountant and I ended up dropping out of school before winding up in retail. We had mutual friends and would see each other a couple times a year as we lived in the same college town.

One summer, Claire ended up getting trashed at my apartment for a friend's birthday. She had made several strong sexual comments toward me but I laughed her off as drunk. But as I woke up a little hungover myself the next day, I opened Snap and told her an honest truth: I had found myself jerking off to dirty thoughts I came up with about her every now and again.

I was immediately mortified after hitting send. I suspected she would block me and not speak to me again from my being so forward with her.

Instead, she was pleasantly surprised.

Claire was slightly bigger and didn't love her looks. She had slimmed down significantly a few years earlier and had gained some confidence but she ended up putting the weight back on. It was during her slim down I first found her floating through my head as I was desperate for a muse to come to. Her multiple requests to see my dick the night before brought all of that back to mind.

Over the next few years, we became sexting buddies. We shared all kinds of details about our past sexual histories, our likes and dislikes, and even things as mundane our days. We never tried to be together, instead getting more gratification from watching each other get off on Snap late at night. We both drifted in and out of relationships and we respected the boundaries when the lines needed to be drawn. But I'd be lying if I didn't send her the results of my jerk off session randomly or if I wasn't happily surprised to see Claire filming herself plunging a toy in and out of her pussy every now and again, relationships or not.

We would see each other in public and act like our sexting relationship didn't exist, aside from a few whispers. That changed about a year after we started, when she needed a place to crash for two weeks while some work was being done at her house. I was living with a friend and splitting rent so I could save towards a down payment for my own place. My friend liked Claire, so I offered her my room. I had no problem falling asleep on the living room couch as that summer's heat was brutal and I felt like the living room got the best air flow.

So imagine my surprise, when Monday through Friday for both weeks of that 2 week stay, Claire would come out to the living room, freshly showered for work. She was in her robe and nothing else and she woke me up. Our sexting became physical then, as we took turns each morning going down on each other until my friend opened his bedroom door at 6 and padded down the darkened hall way to the bathroom.

I could probably write about that separately now that I think about it.

After Claire went home, it was back to semi-regular sexting for us. But now we both had a taste for the real thing. Three years later, shortly after the new year, we found ourselves truly without significant others for the first time since all of this began.

I opened a Snap message from her as I was sitting down to watch some TV one evening.

I've been so horny today. I really want to feel you inside of me instead of my toy.

I messaged back. What time?

+++++

"It's okay," she had said.

I lowered my head as a half smile came to my face. "No, it's not." I had been so excited to finally be inside of Claire after all the years of dirty talk, and photos, and the mornings I woke up to her guiding my face to her pussy or her pulling my shorts down so she could take my cock head in her mouth, that I hadn't lasted long. This was the second time we had attempted to have sex in a week or so.

Claire was one of those women who was blessed with the amazing gift of having a pussy that would get soaked at the slightest thought of arousal. She had told me stories of how she could have multiple orgasms and how a former hookup of hers had been able to make her come from just nipple play.

I loved her nipples. She would grouse about her small breasts but her nipples were indeed sensitive. They would get hard immediately upon touch and she wasn't shy about moaning. Her moans drove me crazy.

I had once approached her in the bathroom at a birthday party, each of us a few drinks into the night. While our friends and family sat around a bonfire outside, my mouth found her neck while my hands teased her nipples. I continued my gentle, yet urgent kisses on her neck while one hand squeezed her ass and my other fingers found her soaking wet. I fingered Claire to orgasm in less than a minute. Afterwards, she reluctantly broke away from me to rejoin the party, leaving me with a smile and small peck on the lips.

"Thank you..."

Both of our hookups had been the same. My face immediately found her clit and I ate her out loudly. I always split her open with my tongue, sliding gently upwards until I found her clit. That's if I didn't tease her prominent outer labia lips first. I alternated between licking and sucking, sometimes gentle, other times more firm, depending on my mood. She enjoyed it all.

My hands would play with her nipples, teasing, pulling, or pinching. Claire would writhe underneath me, her hands caressing my head and shoulders, rubbing my arms, gripping the sheets. And she would moan constantly.

God, I loved her moans.

After my mouth had brought her to the multiple orgasms she had told him about long ago, she pulled my face up, my mouth and chin covered in her wetness.

"I need you to fuck me."

The romantic in me always wanted to start with missionary but she had told me how much she loved being fucked from behind. She moved from her back to her knees and presented her ass for my dick. As I slid inside of her with ease, I was amazed by how big her ass was in this position.

And how tight she was wrapped around me.

"Fuck..." I groaned. One of her hands reached back to touch my hips as I began to thrust. "You feel so good."

She began moaning as well, her head against the mattress, turned to the left so she could breathe and watch me behind her. My hands squeezed her ass, each thrust feeling like she opened wider to accommodate me.

"Oh shit," I breathed. No, no, no. Not already.

"Go ahead," she moaned, which didn't help his cause. "I want you to come." That was all it took. For the second time in as many weeks, I came hard inside her.

We untangled and I disposed of the condom. We parted ways soon after, as she had an early morning. The clock was close to midnight by the time I crawled into my own bed back home.

But I was fuming at myself. I shouldn't feel bad as I made her come with my mouth both times before I exited the main event early. But I wanted to feel her convulse around my cock. I needed it.

I may have only slept for an hour or three. I soon found himself back in my car, back on the streets, and back in her parking lot. The sun hadn't even risen again.

Claire was surprised to see me at the door when she opened it. "Did you forget something?" I stepped inside and closed her door behind me. Her makeup was half done and she wore a black tank top and a fresh pair of black panties.

"I can do better." My lips met with hers and she received my tongue willingly.

"I don't have much time..." she said as I clumsily backed her towards her bedroom and onto her waiting bed. I pushed the tank top up and my mouth was quickly on her left nipple. My left hand groped her right roughly. Both nipples became hard as rocks, which only made me intensify the attention.

"I don't need much time. I just want to fuck you until you come." I stood to drop my pants and boxers and my hard cock sprung out, the tip glistening with precum. I smiled while I opened the condom and rolled it on my dick. I pushed her panties to the side, revealing her waiting pussy.

With one hand on her waist, I used the other to guide myself inside of her. "Oh fuck," she cooed as she watched me bury myself to my balls. I hooked her legs, raising her ass slightly, enough for her to feel my width against her g-spot. Her calves came to a rest on my shoulders but it felt like I was going deeper. "You fill me so good," she managed.

I was possessed. My strokes were urgent but sure. Her hands gripped the sheets, just like they did when I had his face buried inside her. I locked eyes with her and felt something new: confidence.

"God, you're so tight, baby. I love it." She moaned in response. "I'm gonna make you come all over this dick, just like I always said." Then I felt it. Her pussy squeezed down on me as she orgasmed. It was the best sex had ever felt.

"Oh my God, fuck!" she said through clenched teeth, her eyes closed tight. I increased my pace, my arms wrapped around each of her legs so I could come as well. "Shit, I'm close again!"

But I couldn't hear her as my own moans overtook me. I emptied myself as deep inside her as possible and I was greeted with the same amazing squeeze she had given me a few minutes ago. Out of breath, I withdrew myself and collapsed beside her, my cum slowly rolling down out of the somehow, still functional condom.

"What a way to start my day," she sighed as she swung her legs off the bed to achieve a sitting position. "Feel this." She took my hand and pulled me to her until I was touching the top of her thigh. Her legs were quivering as if she had the shivers. "My legs get like this from your tongue. But they've never shook this hard." She stood up and pulled her panties off.

"No," I said as I pulled myself out of my post-coital stupor. "Leave those on. I want you to keep soaking those same panties thinking about what we just did."

She laughed. "That sounds really hot but these aren't going to be very good underwear after having your dick stretch them to the side for 10 minutes like that hon." She looked at her phone for the first time since I arrived. "Somehow, I still have time to not be late for work." She looked back to me as I tried to work my still very hard dick back into my pants. "But if you don't get that thing out of here, neither one of us will be on time for anything."

"Promise?" I grinned.