Oh, What Fun It Is to Ride

"Are you sure you don't what to go caroling with us?"

"Mom, you know my answer hasn't changed. I'm on break, and I've had a hell of a semester. Tonight, I fully intend to do way more unwinding, and way less freezing my ass off," I replied only half-jokingly.

"What about for a little bit, just a couple of hours? You don't have to do the all night into stayover that we usually do."

"Seriously Mo-- "

"But, it's so much fun! We get to see all the neighbors and family, chat, have eggnog, then crash at your aunt's house. Come on, we've done this every year since you were a baby."

"Oh, I know. We're like the only family collectively under 60 in this community that still does this. I'm sorry, but I really don't want to spend my downtime going door to door, screeching songs at people."

"Riley, I really think you're missing out on -- "

"Mom, I love you, but you know the more you try to sell me on it, the worse you're actually making it sound, right?"

"Alright."

Just when it looked like they were finally leaving the house to give me some much-needed alone time, she turned back around to implore me a final time.

"Last chance. After we leave the house, they'll be no more chances."

"I'm banking on it. Love you. Have fun. See you tomorrow!"

She usually wasn't this persistent, but I knew she was just desperately trying to stop change at all costs. I'm 20, not 10, but she couldn't quite accept that yet. I gave in the first two breaks back, but I really couldn't do that again. I wasn't interested in overcrowded shopping malls or small talk with people I barely saw. All I wanted for Christmas was rest and orgasms. For the latter, I was more than happy to take care of it myself, but I had a certain house sitter in mind. If I was lucky and he was free, I'd have more appealing plans by the end of that night.

Since I'd been back from break, I hadn't had any time to myself. Even locked in my room, I could always hear my parents yelling across the house to each other or hear them calling my name. The number of times I'd had to pull my hand out of my pajama pants or readjust my top to go help with some errand was too depressing to keep count.

Speaking of which, I was pretty sure I just heard the car pull off. I gave it 10 minutes. If no one come back by then, then I knew I was in the clear. I'd gotten a great feeling about that night.

First on the agenda. I hadn't had a proper orgasm since I'd been back. Since the 10 minutes were up, it seemed like I was in the clear. Everything felt perfect. My shower from a little earlier already had me a little horny. Now, I was alone. Plus, the heat had finally kicked in full blast, so there was no need for that pesky, thick pullover or sweatpants. I'd been going commando since I'd been back. I'd just gotten so accustomed to it on campus, that I swear, I can't go back to wearing underwear in the house.

Standing naked in front of my mirror, I couldn't help admiring what I was seeing. My dorm room didn't have enough space for a full-length mirror and neither did the bathroom. A lot of people complained about the "Freshman 15" and campus weight gain in general, but you wouldn't hear any of that from me. It definitely did wonders for me. At least, I thought so. My hips, ass, and thighs were thicker. Hell, even my tits had a little more size. I was still considered on the slim side, but my bottom half was a healthy handful and my chest, a delicate mouthful. Who knew all I needed was consistent dick and takeout to become even more fuckable?

I haven't even touched myself yet, and I was already so turned on at just the sight of myself. My nipples were becoming erect, and my clit twitches were becoming more frequent. I needed to get in the mood.

"Hey Siri, play the playlist 'Sensual Sounds'."

I loved watching myself gyrate to the beat, I still do. I always get a little turned on when I'm dancing in a club or campus party. I always thought it was just the liquor, but I relized it's more than that. Doing it naked was even more tantalizing. The only touch I was allowing myself were my fingers curling through my hair and the occasionally brushes my hands made against my face and neck. Fuck, this was agony, but it was the best kind, so I didn't mind.

Feeling my pussy get wetter with each dip and twirl of my hips felt so fucking good! I didn't know how much longer I could handle having my clit rhythmically squeezing between my lips and thighs without touching myself. But it had been so long since I'd had any privacy that I really wanted to savor it.

I couldn't take it anymore, but I was not ready to fully give in yet. Sliding my hands slowly past my neck, down to my chest teasing my nipples felt so fucking good. My nipples were so receptive. I guess not cumming in 2 weeks can do that to you. I wasn't done exploring yet. I was not normally ticklish, but I couldn't help squirm a little as my fingertips graved the soft skin of my stomach.

Following the trail down to my inner thighs was so rewarding. It felt like every nerve was coming alive with each new stoke of my fingers on my body. I couldn't even control it anymore. My gyrating hips were circling more tightly, pressing my clit with the perfect amount of pressure as I caressed my ass and lower back. Fuck, I looked so good right now. I wished the house sitter cutie from Bumble could see this. In that moment, I'd have loved for him to bend me over right then. Like a psychic, right when he ran on my mind he called, such impeccable timing.

"Hey"

"Hi. You sound out of breath. Did I catch you at a bad time?"

"Not at all. Actually, my mind was just on you."

"Oh really. What were you thinking about me for?"

"Well, you noticed I was out of breath. You fill in the blanks."

"Why would -- "

"Use your imagination, Theo."

"Oh! I-I-I get you now."

"Good. Are you free right now? I know you said you'd probably be a bit busy, but since you're calling does that mean plans have changed?"

"Um... yea. I decided to cancel. I just wanted a more lowkey evening."

"Hmm, how lowkey exactly?"

"No-not too lowkey. Just not up for the party vibe tonight, ya know?"

"Yea, I get you. I'm free tonight also. The 'rents went out caroling, so they'll be out until tomorrow."

"Oh really?"

"Yea. So does this lowkey evening of yours have room for some company at your place, or no?"

"Of course!... I probably should have said that cooler, huh?"

"Nah, it was cuter that way. Since you said you're in the neighborhood, just drop a pin an I'll be over in 15. Does that work for you?"

"Yea, I'm sending it now."

"Cool. See you soon."

I was so glad I decided to use Bumble. The prospects around here were usually pretty grim; and I was definitely not fucking anyone from high school, but I lucked out matching with Theo. He was my age and a junior as well; olive skin, jet black hair, piercing dark brown eyes, and a gorgeous smile, he was just my type. Plus, he was sweet. He constantly complimented not just my looks, but my personality and humor. He admitted he had a thing for girls with curls, specifically auburn-colored ones with dimples, such a charmer. And his toned physique was a plus. I hoped it wasn't just for show.

From the pics he sent me, he exceeded expectations in all the right places. Judging by his muscles, he could definitely pick me up and throw me around if he wanted to. I couldn't wait to run my fingers down his chiseled chest, down his happy trail until I reached his thick cock. I'd been wondering where such a hottie came from. Turns out he was a nephew of one of the older neighbors, and he was housesitting for them until they got back.

I figured with any luck if all went well, we could hook up for the duration of the break, and maybe after. He was in college too, so our breaks would line up. So, so long as they kept asking him to housesit, I'd have access to consistent cock. I'll admit, I may have been getting ahead of myself in that moment. I knew I needed a through dicking down before I could decide if I'd even want more of what he was so eagerly giving.

With his call, it seemed I wouldn't have to settle for only my hands that night. It almost felt like torture having to put my clothes back on, but it'd be worth it. I was not bothering with underwear. I threw on the same outfit. There was no point in attempting to pin back or tame my curls since I fully intended to mess them up against his sheets soon enough. I thought I looked pretty fuckable that way anyway. Especially since you could see my nipples peeking through my sweater.

I made a mental note to grab everything I needed. I wanted to avoid having to make a detour and delay receiving that dick. Boots, check. Coat, check. Plus, I had my keys, condoms, and phone. I was so glad he lived so close by. It would have only taken me 10 minutes, but considering what a great motivator cock can be, I made it in 5.

Fuck, he looked even better than his pics. He was such a gentleman waiting outside in the cold for me. I could see someone was excited.

"Your nose is a little red. Have you been outside waiting for me since we spoke?"

"Maybe. You'll have to warm me up to make up for all the trouble."

"Well, it's the least I can do."

"Yes, it is. Are you parking outside or in the garage?"

"Garage. I don't need the possibility of nosy neighbors aware of my naughty plans for the night. And, I definitely don't need anyone reporting back to my family... or yours. I somehow doubt bringing girls to their house to fuck over the break was a part of the agreement you have with your relatives."

"Good point. Come inside. Are you hungry or thirst or anything?"

"As sweet as your offerings are, I didn't come here for refreshments. Maybe if we work up enough of a sweat and burn off enough calories, I'll take you up on your offer."

"Gotcha."

I'd always seen the older couple in passing. But aside from caroling on their doorstep over the years, I'd never really seen the inside of their house. You could feel the warmth as soon as you stepped in, and it wasn't just from the fireplace. It was fully decorated with Christmas décor. The walls were covered in photos of family and trips from around the world. It seemed they felt that even if they weren't going to physically be here, they still wanted it to feel like a home.

"Let me take your coat. Are you sure you don't need anything to drink. I have some egg--"

"You should really show me the way to your bedroom. I've noticed, you seem a bit more timid in person. Don't tell me you were all talk. You know, I didn't come here to just hold hands and watch 'It's a Wonderful Life'."

I'd heard the term "if looks could kill, I'd be dead right now" before, but the look he just gave me was more of a "if looks could fuck, I'd be naked and bent over already". I guess teasing riled him up. I made note of that. It could come in handy later.

"I figured we'd small talk a little, maybe watch a movie. I didn't think you'd want to jump right into bed... Not that I mind!"

"Theo, I was naked, touching myself in front my mirror when you called me. I sped over here horny, wet, and ready. If you really want, we can watch a movie instead or talk, but that wasn't exactly what I had in mind. So, what so you want to d--?"

Hmm. I guess I didn't need to say much to convince him. The space between us became nonexistent with two of his long strides. Feeling his gaze burning into me as he closed the gap, grabbing me in his arms and pressing me into himself was making my clit twitch. I could already feel myself getting wetter. He had me pinned against the wall with the perfect amount of aggression. I loved feeling his urgency with every flick of his tongue on mine. This was exactly what I wanted. Seeing and feeling his strong body and being taken into his firm grip; fuck, I couldn't wait until he took me upstairs.

It was like he was reading my mind and adding on things I didn't even know I was craving. I love being in charge, mainly because I hadn't met anyone that could make me what to relinquish the reins, but fuck, did he make that idea seem enticing. As I leaned deeper into our kiss, he nudged my thighs open with his knee. I could feel his stiff length pressing into my hip, but before I could even get a chance to fully appreciate it, he grabbed my ass in both hands and lifted me off the ground.

He didn't miss a beat. His kiss deepened as he made our way towards the staircase to his bedroom. As I ran my fingers through his thick hair, he moaned into my mouth. I loved feeling his strong hands gripping my ass as he quickened his pace. Before I knew it, we were upstairs. He slowed our feverish kissing to let me down right in front of the bed. As his dark eyes locked with mine boring into me, a mischievous smirk cam across his face.

"So, what exactly were you doing when I called you? I heard music in the background. I just wanted to make sure I had a vivid picture... for curiosity's sake."

"I was teasing myself."

"How? That answer isn't nearly descriptive enough."

"I was dancing, naked in front of my mirror."

"Hmm. What kind of dancing?"

"Just regular dancing, like club dancing."

"Can you show me? I'm somehow drawing a blank on what that looks like."

"Oh, is that so?"

"Yup. A little demonstration would be very helpful."

"With music?"

"Uh huh. I want to see exactly what you were doing."

The idea of putting on a little show was intriguing to me. I restarted my playlist, and closed my eyes. All the feelings I had in my room earlier came back. It was like I never left. I ran my fingers over the front of my sweater, running small circles over my breasts. It didn't take long for me to really get into it. I teased at lifting the hem of my sweatshirt as my hips twirled to the beat. At each pull of the hem, my top gently grazed my already hard nipples, sending shivers down my spine.

I hooked my thumbs into the waistband of my sweatpants and shimmied out them. After they dropped to the floor, my top quickly followed. I stepped closer to Theo, hips still swaying in time with the melody. With my hands in my hair, I continued to gyrate more aggressively, soft moans escaping my lips as my pussy became more wet. Having an audience really enhanced the experience.

He was definitely enjoying the view. As my naked body swayed inches from his face, he reached out and touched my stomach. Slowly, at first, barely grazing his fingertips against my skin until he brought his other hand to my ass and pulled me closer. As he placed soft kisses all over my abdomen, his hands explored my lower half. He caressed every inch of my thighs, his hands sliding up higher before coming back down slowly to reach behind my knees.

Just as they felt they were going to buckle, he slipped one of my nipples into his mouth. His stiff tongue toyed with it, flicking it slowly at first, but quickly picking up speed. He released it for just a moment, looking up at me with eyes full of lust. He ran his fingers up my thighs again, slipping his fingers into my soaking pussy. He curled his index and middle finger as his thumb drew spirals around my clit. He rhythmically pumped his fingers into my, stimulating my g-spot with each stroke.

It felt like he wasn't even going to give me a moment to catch my breath. My pleasure continued to build. Just when I felt myself on the edge of orgasm, he changed his previous speed. His fervent sucking of my nipples, slowed to soft licks. His fingerfucking curbed to relaxed pumping.

"I don't want you to cum just yet. I want my cock drenched with your cum, not my fingers."

He removed his fingers from inside me, gave my nipple one last suckle, and stood up from the edge of the bed. He took off his baggy long sleeve t-shirt and flung it on the floor. I barely had time to notice the tenting of his flannel pants before they hit the floor as well. I see I wasn't the only one that decided against underwear. His cock stood completely erect. It was the perfect thickness and length for me. I love a man with good girth. I want to be filled to the brim with cock. I don't need one that's as big as a baseball bat or anything crazy like that. I want that when you bury every inch of cock inside of me, there isn't a millimeter of space between our bodies. And that's exactly what Theo was packing.

He kissed me as he gently guided my body onto the bed. He nudged my thighs apart as we continued to explore each other lips and tongues. He trailed his kisses down my jaw to my neck. His tongue swirled onto just the right spot. My back instinctively arched, bringing my chest flush against his. As he nibbled on my neck, I pushed my mound into him. I needed us closer together. I needed him inside of me. Thankfully he got the message. He raised his head and looked me right in the eyes.

"I want to see you face when I slide into you."

He took his cock into his hand staring at me with his piercing dark eyes and guided himself into my soaking slit.

"Uh fuck!"

He slid into me slowly, making me feel every inch. My ankles locked behind his ass. I didn't want him to withhold even a single centimeter from me; and he didn't. It was blissful agony. He knew how much I wanted him, but he wasn't going to let me cum that easily.

"I've been fantasizing about you since we first started chatting. I'm not stopping until you've thoroughly soaked my bed."

At that point, all I could do is moan and nod. It'd been weeks since I'd had anyone inside and months since it felt anywhere close to this good. He gripped my thighs and spread them some more to gain more leverage. He fucked me even deeper than before, but with the same agonizingly blissful tempo.

"Tell me how much you like that."

"Uh, fuck. Don't stop."

"You like when I fuck you deep like this?"

"Oh, fuck yes!"

"Do you want it deeper, Baby? Do you want more of my cock inside you?"

"You know I do."

"Good. Turn around and bend over. I want that gorgeous ass of yours cocked in the air."

I was more than happy to oblige. As soon as he withdrew from me, I rolled over and did exactly as he asked. He wasted no time reentering me. Fuck, it felt so good. He picked up the pace as he fucked me deeper. My nipples brushed against his sheets adding to the ecstasy. He gripped my hips with both hands, pounding into me deliberately. We kept this steady motion up, even as I lowered and arched my back more and he caressed my back. Through all that, he never let up. I hadn't expected him to be bad, but I also hadn't expected him to be this fucking good. I was so glad he wasn't all talk.

He sped up, grabbing my hips and fucking me with faster strokes. Every time I felt myself nearing the precipice, he pulled back and slowed down, teasing me. I could tell he loved how in control he was of my release, and I did too. But still, I'm a bit stubborn and I like having my own way.

As he fucked me at this new, subdued pace, I raised up slightly until I was on my elbows and pulled back until just his head was inside me. With my back arched, I pushed back into him, taking him all in. It was my turn to take control. I replicated his same slow strokes. Every time he tried to take charge, I leaned forward. I wanted to set the pace and tease him the same way he'd been teasing me. Every moan that escaped his lips spurred me on. I wanted him to ache for it as much as I was before.

I wasn't done. I wanted to ride his thick cock until I came. He wasn't the only one that spent the lead up to our meetup fantasizing about our encounter. I wanted to take all of him and watch as he was enraptured by my pussy and the hypnotizing way my hips would take every inch of him in. And that's exactly what I planned to do. I backed into him slowly, a couple more times as I felt his fingers digging in deeper into my hips each time. At my final plunge, I took his full length. We both gasped at the sensation.