Alexa

My name is Riley. I'm 32 years old and live in San Diego, California. I hadn't had a girlfriend in a couple years due to a bad breakup, but lately I had been feeling a longing for a relationship again. I decided to get myself back out there.

It was a rough start. Tried out a couple local bars for a few weekends, but they were usually just packed with white girls who were hell bent on getting trashed and couldn't hold a conversation to save their life. No offense to anyone out there, but white girls just don't do it for me. My past relationships were with latinas... Mexican girls and my last girlfriend was Chinese whom I had met while we were in college. Will definitely not be going down that road again.

While sitting at the bar ruminating on my bad luck I suddenly thought to myself, "Why don't I try one of those dating apps I always hear people talking about?" I closed up my tab and went home, excited to see who was out there for me.

I made my profile. I tried to be as honest and open as I could be. I wanted a good match with someone I could marry someday. Definitely was not looking for anything casual. Then a question in the app for my profile popped up: what is your religious preference? Hmm. That was a tough one. I grew up Catholic. I went to Catholic school up to a point. But once I hit public high school, my family stopped going to church. Except maybe on rare occasions like Christmas or Easter. Hmm. This was a tough one. I know in today's day and age it may be frowned down upon to even be associated with religion, but I thought to myself I'm at least culturally Catholic and I do have faith so I'm going to mark 'yes' for that question.

The matches were alright. I went on a few coffee dates. Nothing where anything clicked for either of us. And while it definitely felt a step up from the bar scene I started to grow a little frustrated at still not finding anyone. After a month I decided to delete the app. I had it deleted for less than a week because - man - these apps are addicting. And it sure passes the time. When I installed it back on my phone a message popped up.

She likes you!

Her name was Alexa. She was beautiful. 29 years old, only a couple years younger than me. Her profile was funny and engaging and she just seemed like a cool, fun person. From her photos, I could tell she was Filipino. She had shoulder length straight dark brown hair, big beautiful lips and these dorky kind of black rimmed glasses that framed her beautiful almond shaped eyes. There were by no means any scandalous photos - nothing like her in a bathing suit or in those trendy yoga pants to accentuate their asses, but I could tell by the modest photos she did have that her body was very attractive. She was compact, maybe 5 feet tall with big breasts - probably 36C - and a cute ass.

We enjoyed many of the same things, but bonded over beer. It wasn't long before we decided to meet. Our meeting was wonderful. She was funny, smart, had a nice teaching job at a local Catholic high school. She actually said a big reason why she chose me, besides me being handsome, was because of my religious preference. It was important that her future husband be a practicing Catholic. It was plain to see by anyone watching us that we were a good match.

After dating for a month or so, we decided to go to a few breweries. It was our first time getting drunk together and we kissed for the first time. Her lips were so soft and wet it was like a dream. We closed out and went to my car and we started to kiss more heavily. She darted her tongue in my mouth and when she knew I wasn't put off by it I did the same. I began to caress her breasts through her blouse as she began to lightly moan and asked if we could go to my place. I agreed. As I turned on my car I looked down and so my throbbing, stiff cock poking noticeably through my jeans.

We got back to my place and quickly made our way to my bed. As I disrobed her I took everything in. Her breasts were shaped perfectly and more than a handful. They were big and natural and hung in a way that made those 'perfect' round silicone tits from the 90's look laughable by comparison. She had big dark nipples that were begging to be sucked, but her body was so overwhelming that I settled for just cupping them as she moaned and ran her hands through my hair.

I laid her on my bed and as I took off her soft blue cotton panties I could see how wet her bald pussy had become. It glistened. My head was spinning, I half-jokingly asked, "Oh, you shave..." she laughed and said, "I'm Filipino, I don't have hair there." I ran my hand across her legs and lightly over her pussy and I said, "I learn something new every day."

Her pussy was fat, plump and dark. As a guy you can't help but take in all the differences of past pussies you've had the pleasure of seeing. Her pussy was immaculate. There was something so primal in how it looked, felt and smelled that my cock got rock hard and dripping with precum.

I laid down next to her we began to kiss and she grabbed my cock and began to stroke it in an almost awkward fashion. Maybe she was just nervous? Her petite hands had a nice firm grip, yet were soft that made me moan. As I gazed at her I saw her eyes were almost transfixed on my cock.

"Do you like the way it looks?" She didn't even look at me she just continued to stare at my dick as she stroked it up and down.

"It's big. Do you like her he way I'm doing it? Does it feel good?"

"I do. But I'll feel even better when I'm deep inside you." I replied.

That broke her gaze and she looked at me and shyly asked in an almost hesitant tone, "How do you want me?" Now, normally in a more sober, less horny state I would at least try to be romantic with me on top but I blurted out, "Get on all fours for me."

"Okay..." she replied sweetly. She duly got on all fours right in the middle of my bed with her face buried in my pillow. She looked gorgeous in that position. Her breasts easily touching my covers and her firm but shapely ass sticking in the air ready to receive my hard dick.

I wanted to give a good impression even in these circumstances so as I took off the rest of my clothes and got behind her I asked, "When is the last time you had sex?" She lifted and turned her head and said, "I've never had sex." She had told me before when we were still texting on the app that the last time she had a boyfriend was over 5 years ago. She said it didn't last long, but I had just assumed they had sex. Guess I was wrong.

"Oh, okay. Are you sure you want to? I'd be fine if you didn't."

"No, I am ready. Just promise me you'll be gentle."

My cock stiffened as I stroked it soon I was using my cock to get her even more wet to get her ready for me. I rubbed the head of my cock up and down on her wet swollen pussy lips. She would moan ecstatically each time my head went down and touched her clit. Before long the lips of her pussy were dripping with wetness. Soon, my head disappeared completely into her ripe and swollen opening.

"Ooo! That feels amazing, baby. Please don't stop!" she moaned with pleasure as I continued to rub up and down. As I continued to warm her up for the pounding I would be soon giving her, I grabbed her left ass cheek revealing her cute butthole. I was getting so horny that I reached my hand to her face and said, "Suck my thumb." Without hesitation she sucked on in until it was good and wet and then I pushed my thumb into her tight little butthole. To my surprise she moaned with pleasure. I asked if she liked that and she said yes.

"Say it then, baby."

"I like it when you stick your finger up my butt, daddy!"

"Good girl.. are you ready for my cock?"

"Yes."

As I entered inside her for the first time in her life, I thought to myself she really was a virgin. For as wet and accepting as her pussy was I only got about an inch in past my head when it felt I couldn't go anymore. I started to slowly go back and forth until I could see my cock going further and deeper in until it was almost half way there.

As I went deeper I felt her pussy tightly grip my cock as she moaned loudly into the pillow.

"OH MY GOD!" she screamed into the pillow.

She was so tight and wet that I soon was close to coming. I could feel as the walls of her pussy began to contract and pulse around my cock. I realized that I wasn't wearing a condom. I didn't even know how she felt about using one or not. I didn't use them ever. I never had one night stands, so going without one with my girlfriends was a must for me. But the thought flickered past my mind as I pumped her from behind.

"Hon, I'm about to cum. Where do you want me t--."

"Cum inside me!"

"Are you sure?"

"Yes! Do it! Please yourself!"

She didn't have to tell me twice. I grabbed her by her waist with both hands and began to pump her harder. Even though my dick was still only making it half way in her pussy, the sheer tightness of her made me not care about going any deeper.

Soon I could feel myself readying to fill her up. "I'm going to cum now!" She moaned louder as I shot huge loads of my seed into her newly christened pussy. I stayed in her for as long as my dick would allow. As I pulled out I saw her pussy completely filled with my thick, white cum. I filled her up to the brim. I smiled as she asked, "How does it look?" I told her it looked like a work of art. She laughed and said it felt good inside her. "I feel like a woman."

I rolled her over on her side and laid down next to her. As my cum slowly rolled out of her soon-to-be-sore pussy she grabbed my arm and drew it over her breasts and said, "I love you, Riley."

"I love you too, 'Lex."

I couldn't wait to enjoy more times with her. As we drifted off to sleep, I began to think of all the things I wanted to do with her. Images of her sucking my cock, her and I 69'ing, me fucking that tight little asshole of hers went running through my mind. I got hard again thinking of her sexy lips around my cock while I sucked her fat pussy. But more than anything I wanted to break in her pussy more so I could really pound her balls deep. But there would be more than enough time for that later.