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It was a week ago Friday. My heart was in my throat as I fumbled to get the key into the door of my apartment. Jean hugged my left arm, my biceps was sandwiched between her perfect tits. She smelled so good. Could I be anymore nervous? A big sweat bead begin to roll down my brow. “Goddamn key.” My hand was shaking like a leaf.
The moment of truth would soon be here. Would it go better this time? Jean was so wonderful. She was definitely girlfriend material. I knew she was out of my league. She really seemed to like me. What did she see in me?
I met Jean at work a few weeks ago. We had great conversations during our lunches at work. She said I was a good listener, she said she thought I was handsome and smart. She liked my beard. When I finally got up the nerve to ask her on a date she quickly agreed and said, “What took you so long? I was beginning to worry you were gay.”
I finally managed to get the door opened. Jean led the way holding my hand. I turned on the lights and invited her to check out my place. “Put in a CD”, I said as she admired my extensive music collection. I had spent hours cleaning the place earlier on the remote chance that Jean would accept my invitation to come back to my apartment.
I knew from our conversations that Jean liked country music so I had spent a small fortune buying some new country CD’s from Target the day before. The only country CD I had prior to that was an old Brook’s and Dunn greatest hits CD.
Jean picked a Taylor Swift CD and put it in the player. “Good choice“, I said. I wasn’t much of a country music fan, but I was familiar with Taylor Swift and considered myself a fan although her songs were starting to sound alike.
Jean was complimentary of my place as she looked around. I opened a bottle of chilled Shiraz and poured two glasses. Jean made her way toward the bedroom and stepped into the doorway and turned on the light and said, “Oh! So this is where all the magic happens, huh?”
I walked toward her holding the wine and laughed at her comment. “Magic? Yeah, I’m a regular David Copperfield.“ Was she serious? Did she think I was some kind of stud or something? The only magic trick I was likely to perform in the bedroom was making my cock disappear.
Jean sat close to me on the sofa and sipped her wine twirled her blond hair and looked at me with those beautiful blue eyes like she wanted to fuck. I knew that look. I wanted to lean in and kiss her but I was afraid where it would lead.
The last time I had a girl in my apartment was six months ago. I met Carly in a BBW chat room. She lives in Waukesha, about 8 miles west of downtown Milwaukee. Carly and I chatted a few times before I invited her over. Carly was as self-conscious about her humongous size as I was about my small cock. She didn’t understand how small it was until I turned on the webcam one night and showed her. I figured that would be the end of our budding friendship but it wasn’t. She made a joke and said how ironic it was that my parents named me Richard, “Dick”.
I normally wasn’t attracted to big girls and Carly was BIG. But I was horny and ready for anything with a hole and a heartbeat. Carly was seeing a lot of different guys from the internet and I made it clear that I wasn’t looking for anything serious. We agreed that this was going to be a one time fuck so I gave her directions and jumped into the shower.
I watched for Carly’s green Saturn to pull into the parking lot. I watched her park and struggle to get out of the car. She was wearing one of those big flowered sleeveless sun dresses. I waited at the door and watched her struggle to climb the stairs to the second floor landing.
I was thankful that none of the neighbors saw her come in. Carly was out of breath when I greeted her with a hug and pulled her into the apartment and closed the door behind us. Carly kissed me passionately our tongues were in and out of each other’s mouths. She held my face and sucked on my tongue. She really was a great kisser. We didn’t waste any time, I led her to my bedroom. We sat on the edge of the bed and continued to kiss as Carly groped my hard little chubby through my shorts.
I felt Carly up through her dress. Her tits were gigantic, 52F she said. Carly wasted no time pulling her sundress off and tossing it to the floor. She placed my hands on her braless tits. Her nipples were dark and the size of saucers. I helped Carly slide out of her granny panties, revealing a thick dark hairy bush. I hadn’t expected that.
Carly complained that she was naked and I was still fully dressed.
Even though Carly had seen my cock on the webcam, I was uncomfortable getting undressed in front of her. Being naked in front of people is very difficult for me. I undressed with my back to her and walked over to turn out the bedroom lights but light shining in from the streetlight still lit the room enough for Carly to see me. I summoned my courage and turned to face her.
My penis is almost 4 inches when it is fully erect. It was erect when I showed it to Carly on the webcam. But now butterflies and anxiety had caused my sad flaccid dick to shrivel up to nothing. Carly motioned for me to come back to the side of the bed and then wasted no time taking my little pinky dick into her mouth. It sprang back to life and I begin to feel less self-conscious. Carly was an expert cock sucker. She sucked dick better than the $20 whores on Greenfield Ave. I was hard immediately. Carly stopped to admire her handiwork and praised my “little pickle”.
Carly loved giving head and she knew she was good at it. I figured she had probably sucked hundreds of cocks. She massaged my balls with her left hand while she milked me with her wonderful mouth. Her right hand made it’s way around to my ass and she teased my asshole with her index finger. It felt really good and I wondered if she was going to stick her finger up there. I started to pump, fucking her face. I could feel a powerful orgasm building. She inserted her index finger to the first knuckle. I started to get light headed.
“Not so fast baby”, Carly said as she stopped slurping my dick and slid back on the bed and spread her legs. She spread her hairy pussy and told me it was my turn to lick her pussy. I crawled up between her legs and spread her thick cunt lips with my thumbs.
The scent of her pussy was powerful and musky. I hoped it tasted better than it smelled as my lips and tongue tentatively met her labia and huge hair matted clit. It wasn’t as bad as I feared. I licked her slowly from the bottom of her slippery slit all the way up to her clit. Carly’s moaning assured me that I was doing it right. I couldn’t help but wonder how many dudes’ spunk was mixed in these juices that were flowing out of this unwashed fat snatch and soaking my bed sheets.
Carly thrashed around and moaned loudly as I concentrated on her clit. I flicked it and sucked it while shoving three fingers, then four deeply inside her loose pussy. “Bite it baby”, she pleaded. “Harder” she encouraged. Carly’s abused clit had been desensitized from so much sex. I was biting it really hard and she was loving it. I felt her snatch tighten around my fingers and she grabbed the back of my head and held me tight. I struggled to catch a breath and kept sucking and biting on her clit, hoping this would be over before I suffocated.
“OH FUCK YES”, Carly grunted as she started to cum. She squirted a warm stream of “God knows what” from her fuck hole , ejecting my fingers in the process and soaking my mattress. “Get up here and fuck me baby”, she demanded. I knew this wasn’t going to work, but I was going to give it my best shot.
I slipped my cock inside her. I don’t think it made it past her outer lips. The look on her face told me she was feeling the same thing I was. Nothing. It was like sticking your big toe in a bathtub. I tried to pump but I kept slipping out. Carly offered to get on top. That was a position that worked for me with a previous girlfriend, but Carly was way too big to get on top. I kept thrusting not sure if I was in her pussy or fucking one of her fat folds. Wherever my cock was, it felt pretty good and it had been several days since I had jacked off and I really needed to cum.
Carly pretended to be enjoying my unskilled fucking. She wasn’t very convincing but it didn’t matter. I was determined to get a nut and with a few more thrusts I finally blew a big cum load somewhere between her fat thighs. I rolled off her and panted while my cock shriveled up inside me.
Carly cleaned herself up in my bathroom then we made polite small talk while she dressed. I gave her a final hug before saying goodbye hoping no one would see her coming out of my apartment. We chatted a couple of times after that, but soon we didn’t bother. A couple of days after our encounter, I noticed Carly had added a comment to her profile saying that she was only interested in meeting guys who were well hung.
“What are you thinking about?“ Jean’s sweet voice snapped me back to my current predicament. She looked at me with that same sex starved look. The memory of my disappointing encounter with Carly fresh in my mind, I wondered if I should tell Jean I was feeling sick before things went any farther.
Without warning, Jean hopped into my lap, threw her arms around my neck and kissed me hard. She pressed her boobs into my chest as she straddled me. “You’re so tense Dick” she said. “Not used to having a girl take charge?” I put my hands on Jean’s trim waist and pulled her close and kissed her back.
Then Jean started to grind herself into me. Panic stricken, I realized she wasn’t going to feel what she was expecting as she dry humped my lap. I pushed her off and jumped up. Jean looked rejected. “What’s the matter Dick? I thought you wanted me.”
I told Jean it wasn’t her. I assured her that I wanted her but that there was something she needed to know before we went any further. I gulped down the wine and composed myself. My voice cracked as I told Jean, “You need to know I have a very small cock and I am very sensitive about it.” Jean smiled. “Shit, you scared me. I thought you were going to tell me you had Herpes or something like that.” Jean continued, “Listen Dick, I think you’re a great guy and I want you to make love to me. I’ve been with guys who had small cocks before. It’s no big deal. You guys worry too much about cock size.”
“Whew” That was a big relief. I rejoined Jean on the couch and we began to make out like adolescents. I unbuttoned her top and unfastened her bra and started sucking on those awesome tits. I licked and sucked on her nipples. Her erect nipples were very long. Jean said they were very sensitive and she loved having them sucked. I slipped my hand under her skirt and ran my fingers across her moist thong covered pussy. We kissed again and I slipped a finger under her thong and across her shaved pussy lips. I reached under her skirt to remove her thong taking time to smell the wet crotch before throwing it on the end table.
I started to walk across the room to turn off the lights, but Jean grabbed my wrist and pulled me back. “Leave the lights on baby”, she said. Jean stood up and pulled my polo shirt over my head and then began to unbuckle my belt.
We were now beyond the point of no return. No stopping now, I just let her do her thing and watched and waited for her reaction. Jean got my belt loose and snatched my slacks down to my knees with one hard eager jerk. She helped me step out of them and kneeled before me, preparing to pull my briefs down.
Jean slid the briefs down revealing my hard little cock. She couldn’t hide the look of disbelief. A look I had seen many times before. “I told you it was small.”
“No, no it’s fine”, she lied. She stared at it for a moment before moving her hand up slowly to touch and then stroke it. She touched it like it was some kind of oddity. “I love your little cock baby. It’s so cute.”
Jean pushed me back onto the couch and straddled me again. She lowered herself down slowly guiding my cock into her bare pussy. So wet and tight. She rocked back and forth and we kissed passionately. I slipped out a couple of times, but Jean was ready with her hand and guided me back in right away. Her breathing got faster and she made a cute squeaking noise. She pushed me all the way down on my back and rode me cowgirl style for several minutes having several orgasms before collapsing onto my chest panting.
I had never made a woman cum with my dick before. Jean stroked my chest hair and smiled. “Something about your cock in that position works for me baby. You were touching me in just the right place. I came 4 times.” she said.
Jean kissed her way down my stomach and to my crotch. She licked my cock shaft and began to suck on my balls. She stroked my cock while sucking my balls. She eventually made her way back to my cock and sucked it hard using her lips tongue and fingers to bring me to an explosive climax. Jean kept right on sucking as I ejaculated in her mouth. A couple drops of my cum leaked from the corners of her mouth, but she continued to suck until I was dry and she had swallowed every drop. It was without a doubt the best blowjob I ever got.
“I hope we didn’t just fuck up a good friendship.” I said as we relaxed naked on the couch. Jean shook her head “no”. She didn’t say a word. A couple minutes later she scooped up her clothes and headed to my bathroom to get dressed.
She emerged a few minutes later, all dressed and put together. Her hair and makeup was fresh. You would never guess that she just had sex. “I need to get home and let my dog out.” she said. Funny that she had never mentioned a dog before.
I waited until Sunday afternoon to call Jean. I didn’t want to seem like I was too eager. She didn’t answer her phone so I left her a message. Later she sent me a text message saying she had to visit a relative in the hospital. She said she would see me at work on Monday.
Monday morning I couldn’t wait to get to work. After our regular Monday Staff Meeting, I made my way down to Jean’s department with a lame excuse to talk to her. Several of the girls were whispering and snickering when I approached Jean’s desk. Jean seemed withdrawn. She told me she regretted that she allowed herself to get intimate with someone from work and suggested that we take a step back.
She said she was sorry and she thought we should keep things strictly professional from now on. “It’s not you, it’s your penis! It’s so fucking small I don’t want anything to do with you!” she told me seriously.