Not What You Expected...

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I like to think I was a very pleasant surprise...
2k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 07/11/2014
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I couldn't believe I was doing this. Would these cheesy hookup sites really work? I was so tired of jerking off and wading through fake profiles. I needed to take matters in to my own hands so that I wouldn't have to use my own hands later on... ;)

I know I'm not the most attractive guy. 5'9", 195 lbs... I've got a bit of a belly and I'm really pretty average. So to think I could pull off one of these arrangements felt pretty silly, but I was horny and wanted to give an orgasm so badly. When I'm with someone, I can't get off until she does. Her face as her back arches under my touch lights a fire in my blood.

So I wrote the ad:

"I'm pretty nervous about this, but I'm horny and really just want to please a woman today. I'm pretty average but I know my way around a woman's body. I just want someone I can explore with my hands and tongue. There would be no reason to reciprocate unless you're absolutely driven to after I satisfy you! ;)

If this sounds interesting, hit me up!"

And I hit send, seriously not expecting anything. Did I sound stupid? If someone did reply, could I really deliver?

I shook my head and got up from the computer, telling myself how stupid I was.

I went to the kitchen for some water, and my phone vibrated in my pocket. New email.

I opened it, and it was from you. "Hi! Um. I can't believe I'm doing this, but I haven't been able to orgasm on my own for months. Your ad felt almost like a challenge, daring me to give you a try. I really hope you're not a punk kid out for some laughs. Your reply with a pic gets mine."

I couldn't believe it. I sat down, fixed my hair as best I could, and snapped a selfie.

I sent it to you with the message, "I'm very real. Don't write me off at first glance. I have a very talented tongue. I can't wait to see your pic!"

My heart was pounding as within five minutes, I received your reply. "Hey, you're not that hard to look at! Most guys send dick pics. I appreciate the respect. Here's me. Call me if you like what you see!"

The picture nearly made me pass out! You were better than anything I could imagine! Your long dark hair tossed to the side and draped over your shoulder. Your bright blue eyes stared straight at me and you wore a simple t-shirt, but god did you fill it!

My cock hardened and my heart skipped a beat as I actually dialed your number!

I won't bore you with the details of our call, I'm sure you remember how once we got over the initial awkwardness we actually talked for hours! We had so much in common! As I could feel the conversation coming to a close, I asked, "So when can I come over and satisfy you?"

You laughed nervously. "Oh yeah! I almost forgot what this call was supposed to be about!" Your giggle was so intoxicating to me I felt my head spin. I was starting to get nervous about how I would behave in your actual presence! "What are you doing tonight?" You cooed.

"Hopefully you!" I laughed.

"Tonight it is then!" You gave me your address and directions and I hung up the phone panicked that this could end terribly.

...

It was dark as I nervously rang your doorbell. I wore a nice button up shirt and slacks. I opted for underwear, hoping I would get a chance to watch you strip each layer off of me later...

You answered the door and you were so much more beautiful in person! Your thin blouse was open just enough to reveal just enough cleavage... I noticed you had a bit of a belly yourself, and I found it adorable! Your skirt clung to your round hips and ass in just the right way as you walked me in. You motioned to the couch, where you had two glasses and a bottle of red wine on the table. You had already poured. "I thought this might help us relax..." You said as we sat down.

I faced you and drank you in with my eyes as I sipped the wine. "God, you're beautiful!" I said.

You looked down and away. "Stop. You don't have to do that. We both know why we're here. We can't get any action any other way..."

Your sadness at your own self image made me crave you even more. I had to show you how wrong you were.

"Ssssshhhh..." I said, gently caressing your cheek. "I don't believe that about you for a second."

Before you could argue, I leaned in and kissed your mouth. I appreciated that there was no lip gloss or lipstick in the way. You took a deep breath and grabbed the back of my head, pressing my mouth harder against yours. Your strong lips parted in a sigh and I slipped in my tongue, slowly caressing your tongue and teeth with my tongue.

"Mm! Oh god!" You whispered. Your hand rested on my thigh and I felt it inching up...

I pulled away. "I think you forgot. You first, remember?"

Your face and chest were flush with excitement. I could see your nipples pressing hard against your bra. "You're so good at kissing. Are going to do that between my legs?"

"That and more..." I said. I leaned forward and kissed your neck. You accepted my gentle nudges to get you to lay back on the couch. I kissed along your collar bone as my hand slid along your outer thigh, pushing up your dress. You moaned as I came close to touching you between your legs.

I got on my knees on the floor beside you and you stretched out on the couch. "Come here, you..." You said, pulling me back for another kiss. I ran my hand up your blouse, feeling the smooth skin of your belly. I felt you jump a little and then I slipped my tongue in your mouth and you relaxed, sliding your tongue around mine as well.

You broke the kiss as I inched my hand up to your breast. I looked in to those pale blue eyes as I found your hard swollen nipple through your bra.

"Oh GOD yes!" You moaned. You sat up and I unbuttoned your blouse while you unfastened your bra. We tossed the two aside and I took the closest nipple in to my mouth. It was large and hard and I teased it with my tongue as I sucked it. It popped from my mouth and I grabbed the other one, my hands dropping to your wet panties as I sucked it.

We moaned softly together as I tongued your nipple rapidly and caressed your pussy lips through your panty. Your hand grabbed at my crotch, but a deal was a deal. "Don't go there yet. Remember our arrangement..." I said, kissing down your belly.

"Okay. Okay okay..." You panted as I kissed you lightly through your panties. I grabbed at the waistband of your skirt and you lifted your ass so I could pull it down along with your panties. I gently ran my tongue up and down your pussy lips, careful not to part them yet.

"Oh my. Oh my god!" You moaned. Slowly, I inserted one finger. "Yes! Jesus, yes!" I tongued your swollen clit as I slowly hooked my finger. When you gasped and convulsed, I knew I'd found the right spot and focused on gently, rhythmically, lightly rubbing that spot. Your breasts heaved as you panted. I looked up at you through your ample breasts and sucked your Clit without changing the pressure or rhythm of my finger. You grabbed my hair and pulled and I felt your pussy tighten. I knew you were close.

Your hips bucked and now I increased the pressure, moving my finger faster and deeper...

"Oh god! Jesus I'm gonna cu... I'm gonna cuuuummmmm... Ooooooohhhhhhh fffuuuuuuuucckkkkkkk!!" You were bucking so hard against my hand and your juices flowed down around my fingers. I lapped at it with my tongue as I slowed my pace and finally pulled my finger out and pressed my palm against your quivering pussy.

You moaned and I pressed my palm harder against you as I kissed you long and hard on the mouth. Your breathing slowed, and I took my hand away from your hot wet crotch.

"Oh my god, baby." You said. "I can't remember the last time I came that hard."

I kissed you and said "I'm glad."

You laid back and sighed. "I need to make you cum now."

"I promise you don't have to."

You nodded furiously and said, "Yes I do!"

I couldn't say no to that. "God I want you. Okay. But let's go to the bed, okay?"

You laughed and agreed. You sat up too quickly because you had to steady yourself with my arm. "Whew! I'm a little dizzy!" We laughed and you got up. I followed you, watching how your dark hair cascaded down your back, almost to your bare ass. I watched how your ass moved and I knew I would have to give it a lot of attention later.

I closed the bedroom door behind us, and you grabbed the collar of my shirt and pressed me against the door. You shoved your tongue in to my mouth and I grabbed your ass with both hands. Your hands unbuttoned my shirt and slid it down my shoulders. When it was free, I pulled my t-shirt off and you kissed my chest and nipples. "God I love a hairy man!" You said.

"I'm glad you liiiiiike it! Jesus!"

Your hand was down my pants now, caressing my cock as you tried to unfasten my pants with the other hand. I did it for you and you pushed everything down as you swallowed my very hard shaft!

"Oh! Oh god yes! Oh baby oh baby oooooohhhhhh..."

You stroked my shaft as you took my balls in to your mouth, one by one. You looked up at me and said "Do you like that baby? Do you like how I stroke your cock?"

I could only nod. You smiled and took both balls in to your mouth, swirling your tongue around them while you pressed my penis against my stomach.

My balls popped out of your mouth and you let them rub your cheek while you kissed up and down my taint, almost to my asshole and back to my balls. I moaned as you licked my balls and let my penis fall, gently smacking you. I flexed my penis so that it bounced on your face as you licked and sucked my balls. You giggled and sat back, placed your hands on my hips, and pushed my cock down your throat. I'm too big to get all of me in your mouth, but you came very close. You started bobbing your head and I felt my balls tighten.

"Oh god! Oh god baby yes! Yes, make me cum!"

You pulled me out of your mouth and stroked my soaking hard penis and said, "I want your cum all over my chest!"

"Oh god, yes!" I said. You straightened up and wrapped your tits around me. I grabbed them and squeezed them together and fucked your tits, thrusting harder and harder.

You grabbed my ass and looked up at me. "That's it, baby. Fuck my tits! I want your warm goo all over them! Oh! Oh god FUCK!"

"Ooooooohhhhhhhh SHIT baby!" I moaned as my load shot between your tits and hit your chin.

"Oh god yes!" You said, taking me back in to your mouth. My dick jumped in your mouth again, coating your throat. You moaned and gulped and licked me off.

You stood up and wiped your chin, licking my load off of your hand.

"God you taste good."

I smiled and brought you to me for a long hug. I felt my now flaccid penis starting to get hard again.

I choked down the urge to fuck you right then. "Shower?" I asked.

"Please!" You said...

We walked to the bathroom holding hands, as I imagined all the things I could do to you there...

End of part one.

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