The 7-Day Challenge Pt. 02

Amateur

The first day of the challenge to win James’ heart. Don’t expect Momma to play by the rules…

Monday May 29th, 1:15pm

I was preparing a new fixed-gear single-speed bike, (otherwise known as a “fixie”), for delivery. It’s called that because the gears are fixed – the drivetrain has no freewheel mechanism. It’s extremely simple – the chainwheel moves, the chain moves, your legs move. Myself, I think fixies make no sense unless you have massive moose thighs, but some people just love ’em.

My boss, Roger Layton, had stepped out to lunch, so when I heard the bell on the door jingle I went out to the showroom to help the customer. Lo and behold, it was Momma.

Her hair was tied back, she was wearing a tight white V-necked T-shirt that said ‘They’re Real, and They’re Fabulous’ on the front, tight jeans and cowboy boots. As I walked up to her she turned the lock on the front door and flipped the “Open” sign to “Closed”.

I was afraid I already knew the answer, but I had to ask, “Momma, what are you doing here?”

She sidled up next to me, and began rubbing herself on me like a housecat in the mood for attention. “Now since when do I need permission to come and see my only son?” Her hand brushed across the crotch of my coveralls and she smiled seductively.

“Your boss is out, how about you take me back into the shop so you can show me your toolbox?” Standing on tiptoe she brushed her lips across mine, and whispered in my ear. “I’d really like a personal tour, and I’ll make it worth your while.” She turned me around and gave me a light shove towards the workshop entrance.

“Now, Momma,” I protested, “the challenge doesn’t start until 5:30pm tonight! Besides, Roger will be back any minute.”

“No, he won’t. I saw him today while he was standing in line waiting for his sandwich at the deli. I told him I had a ticket to the matinee showing of that that new superhero movie at the Cineplex, but it turned out couldn’t use it and offered it to him. I’m sure he’s sitting there right now, munching his popcorn and enjoying his superheroes like a good little boy.”

We passed through the workshop entrance, which was one of those old swinging kitchen doors with a porthole in it. Just to the left was Roger’s desk, covered with files dating back to when he opened the shop in 1998. I had somehow managed to drag Roger into the 21st century; in the middle of the piles of files was the monitor for a desktop computer I had given him for Christmas.

The desk had another Christmas gift I gave him: a 5-wheeled pedestal executive leather chair with all the ergonomic adjustments. It was big and comfy and Momma pushed me right down in it. In a flash she was on her knees with the fly to my coveralls undone, sucking furiously on my cock. Any protest I was trying to make about her being unfair to Katie somehow died in my throat.

I lay my head back as she sucked, licked, and caressed my cock and ball sack. “Just think,” she said in between slurps, “If I win, I can be your little whore. You can brag to your friends about what a good little cocksucker I am. You could even bring them home, they can watch while I suck you, or I can suck them too. I can suck a lot of cock. I’ll do anything for you, James.”

My head was close to exploding from pleasure. She took her mouth off me and continued her dirty dialogue as she stroked. But if she thought I liked it…well, it turns out she was right!

“I had a date last week. I was sucking this guy and I told him my son was bigger.” Her hand was going up and down my slick cock in a frenzy, and I was drawing close to my release. “I thought he would freak out and leave, but it made him hornier, more competitive, he ended up fucking me really hard, asking who was better now. I lied and told him he was, but tonight I’ll be able to really compare notes and find out, won’t I?”

Instead of answering, I groaned loudly and shot my load. It flew across the room, landed perfectly on the seat and spokes of the fixie bike I was getting ready for delivery at 2:00pm. Wearing a huge smile now, Momma rubbed my cock across her face. “You liked that. You’ll see how good I can be tonight, won’t you?”

Oh NO! The fixie! Panicked, I pushed her to the ground, got to my feet and zipped up. “Damn it, Momma! I had this bike almost ready to go, now I have ten minutes to clean my cum off the seat before the guy gets here! GET OUT!” The more I thought about it, the madder I got.

Turning away from her, I set myself to cleaning up the bike, deliberately ignoring Momma. I heard the bell on the door jingle, and she was gone.

Monday, 5:30pm

Thanks to Momma’s visit I got off work a little late, so it was 5:48pm when I tapped on Katie’s door, still dressed in my work clothes: sneakers and coveralls with my name (“James”) over the left front pocket.

The door opened, and there stood my vision of loveliness. “You’re late, darling” she said, standing up on tiptoe to demurely kiss my cheek, “but you’re the boss, so it’s ataşehir escort OK. I’ve just been on needles and pins waiting for you.”

“I’m sorry I kept you waiting my love,” I told her as I hugged her, catching the sweet light scent of her soap that I loved. “Let me go change clothes.” I took my messenger bag into the bathroom and changed into some dark blue slacks and a light grey dress shirt, and swapped my sneakers for some casual brown loafers.

“You clean up nicely,” she said, smiling as I came out. Taking her hands in mine, I stepped back and looked her up and down. Her beauty took my breath away. She was the essence of innocence.

She was wearing very subtle makeup, her bright red lipstick the only thing that hinted at something not so innocent. Her shoulder-length dishwater blonde hair was now trimmed fashionably, and she had added bright blonde highlights that shimmered in the light, a white bow perched enticingly above her right ear.

She was wearing a pretty summer dress, knee-length, yellow with small white polka-dots. The button-down front of the dress tightly clung to the curve of her big breasts, but the high neckline kept things demure, not a hint of the sweet cleavage beneath. The elasticized waist pulled the line of the dress back against her thin body, accenting the swell of her breasts from underneath.

From her knees on down, silky smooth legs led to feet encased in dress sandals with demure 1″ heels and two white leather straps with buckle closures. Her recently-pedicured feet were perfect, her toenails glistening with innocent clear polish. She was an angel, all she needed was wings.

On the table was a meal fit for a king. “I hope you like it because tonight I want you to see how I’ll cook as your wife.” As I sat down, she unfolded a fancy cloth napkin and laid it in my lap. Was it an accident that this chaste little angel brushed the back of her hand against my cock when she laid the napkin down?

“Katie, this all looks fantastic!” I exclaimed. And it was: chopped Italian style salad, lobster bisque, and perfectly prepared NY strip steak, slightly pink in the middle, just how I like it. We sat and ate quietly, me savoring each morsel. Katie seemed nervous and only picked at her food, but after I finished and genuinely praised her culinary skills, she started to relax.

After we finished eating dinner, Katie went into the kitchen and brought out two tall fluted glasses and a bottle of sparkling wine. Putting them next to each other on the table, she poured a small amount of champagne into each glass, let the froth settle for a moment, then filled them both three-quarters full.

She looked into my eyes as she raised the glass so I could take it. “I wanted everything perfect tonight. I even read an etiquette book on how to pour champagne, darling. I love you so much.”

“And I love you, sweetie. Although I didn’t show it, when Momma challenged you I was scared you’d back down and I’d lose you. I can’t tell you how proud I am of you and your courage.”

My little blonde angel looked down and blushed. Her eyes started to tear up, which I found, um, stimulating. (I’ve since found the condition is called dacryphilia – sexual arousal from crying or tears – and yeah, I have it!) I stood and went over to her, wrapping my arms around her from behind. She smelled enticingly of soap and spices, and it was all I could do not throw her on the floor and take her. “Please don’t cry, sweetie, you’ll ruin your make up.”

She wiped her pretty eyes with her hand, and regained her composure. “I’m sorry, James, this whole thing is kind of overwhelming. I just really really love you, and I don’t want to lose you.”

I felt the same way, but I didn’t want to tell her in case she ended up losing the challenge. It would make the heartache worse. “I know it’s hard sweetie, but hang in there.” I hated myself for saying that, it sounded so trite. But there was one other thing that I had to ask that was bothering me.

“Baby, you look amazing and this meal was off the hook, but what about your spending? I mean, this stuff was not cheap, and your debt was one of the reasons why we’re doing this.”

I thought that question would throw cold water on the evening, and I might end up back in Momma’s arms a few hours ahead of schedule. Instead, a teasing smile came over her face. “I did charge some stuff to get ready for this week,” she said in a teasing low voice, “but I’m sure you can understand how they were necessary investments.”

Her hand crept up to the front of her blouse and unbuttoned the top three buttons, revealing some delicious-looking cleavage. “But now I have something for you. Reach in there and see what you find.”

I gingerly put my fingers down in between those luscious mounds, and to my surprise I felt a small envelope. I gently eased it out – it was about 2″ x 3″ – the kind you get gift cards in. “Go ahead, open it.” I did, and inside were pieces of her cut-up credit cards. I felt her kadıköy escort bayan hand reach down to caress my cock through my pants. “No more credit cards until I get my debt paid off. I swear.”

I dropped the envelope and swept her into my arms, kissing her deeply. I wanted this woman, and I wanted her now. I pressed my hardening crotch into hers and squeezed her ass as we kissed.

She melted into our embrace for a moment, but then pushed away from me gently. “Wait here. I’m going into the bedroom for a second. This is a special moment for me, and I want it to be perfect for both of us.”

She turned and headed into the bedroom. I uttered “Katie, I love you so much.” It just slipped out – I was overwhelmed with emotion and raw physical desire.

She looked back at me and smiled. “I know,” she whispered, and winked.

In a few minutes (that seemed like hours – why does time slow down when you’re horny?) she called out “I’m ready for you, James.”

I was in that bedroom in two steps. It was dim, lit only by four or five candles around the perimeter. Rose petals were sprinkled here and there, mostly on the white bedspread. And there she was, sitting up against the headboard, wearing a long fluffy white robe tied at the waist by a matching belt. She was modestly covered up from her neckline to her ankles, only the curves of her significant bust line giving a hint at the pleasures beneath.

I was lost for speech as I stared in wonder at the beauty before me. At that moment, Momma’s lips on my cock earlier became a fading memory.

She spoke softly, gently, in a voice that made me weak in the knees. “We’re not married yet, but to me this is our wedding night. You’re my first, James, and I’ll always be your woman whether you marry me or not.”

I walked over to the side of the bed, bent over and pressed my lips to hers. I lightly touched the fingertips of my right hand her face. It was all I could do now to keep my balance and breathe.

“Why, James! I’m the one who’s becoming a woman tonight, I should be the one trembling. What does this mean?” She was blushing, but at her modesty or my own I wasn’t sure.

I found my voice again. “It means I’ve never seen any woman anywhere that I wanted more than I want you now, Katie Farmer.” I held out my hand. “Take my hand, I want you to see something.”

She held my hand, and I helped her onto her feet and led her to the full-length mirrored door of her closet. “Stand here, and don’t move,” I told her. “Keep your hands and arms at your sides until I say otherwise. Look straight ahead at yourself. Do not look at me, do not make eye contact, do you understand?”

“Yes, James,” she responded.

I leaned forward, inhaled her scent again and lightly kissed her neck. “Whose beautiful neck is this?”

“Yours, my love,” she answered softly, giggling.

I reached around and undid the belt knot, sliding the robe off her shoulders exposing her upper back. She held the front of the robe in place over her marvelous breasts. I kissed the skin over each shoulder blade. “You’re such an angel, I’m guessing you’ll be sprouting wings here. Whose beautiful shoulder blades are these?”

“Yours, my love,” she answered again.

Gently, I pulled the robe down so it lay like a wreath at her feet. She was fully nude now, but I dared not look, concentrating instead on the heavenly skin in front of me. I placed light kisses in the hollow at the small of her back, then covered her ass cheeks with a few light kisses as well. I could feel her trembling slightly now.

“Whose tiny ass cheeks are these?”

“Yours as well, my sweet love.”

Ever so gently, I parted her ass cheeks. I kissed the crevasse there, even planting one on her tiny bunghole. She gasped at that.

“Whose little rosebud is this?”

Her knees were noticeably quivering now. “Yours,” she answered in a quavering tone.

I removed my clothes and shoes now so I was totally naked. Moving around in front of her, I saw her completely naked for the first time. My head felt ready to explode. My cock, too.

I knelt down and kissed each toe, then each knee, then alternated a left and right series of kisses upward between her thighs.

“Whose tiny toes are these? Whose incredible knees and thighs are these?”

“James, I’m feeling weak, I may fall.”

“Don’t worry, my love. I’ll be here to catch you. Answer the questions please.”

“All are yours, my love. All of me.”

With my face now at the top of her thighs, I caught the tangy scent of her womanly juices. I leaned in and worked my lips past her outer labia into her moist pussy. I placed a kiss on her wet inner lips.

“Ahhh, James!” she gasped.

“Whose little wet kitty is this?”

“Yours, please, take me now my love!”

“Not so fast, Miss Farmer.” I stood up and took a breast in each hand, kissing each nipple. My eyes open now, I could see her struggling to keep her hands and arms at her sides instead escort maltepe of throwing them around me.

“And whose luscious tits are these?”

“Yours,” she whimpered. Again, tears. Whether from excitement or anxiety, I wasn’t sure, but I liked it. Very much.

Taking her chin in my hand, I tilted her face towards me and give her a soft kiss on those tempting lips.

“Whose luscious lips are these?”

This time, her arms flew up and wrapped themselves around my neck, the kiss becoming deep and passionate. “Please, James. Take me now! I want you so much!”

I picked her up and laid her gently down on the bedspread. Remembering there would be blood, I quickly a grabbed a white towel from the bathroom, and tucked it under her sweet bottom.

Moving around so my lips would be on hers, I kept kissing her as I eased myself down over her tiny body. Reaching between us, I positioned my cockhead at her moist portal and pushed, ever so slightly. The lips parted, and accepted the first half-inch before I encountered the barrier.

Involuntarily, she gasped very softly. This was it. A gentle push, some slight resistance and suddenly I felt the tissue give way, an inaudible thing save for the slight cry that escaped her lips. I didn’t move, but I felt a small trickle of warm blood slowly stream down my balls onto the towel.

“How do you feel? Are you all right, darling?”

She murmured, “It was a little uncomfortable, but better now. Try sliding in a bit more.” I entered a couple more inches. “Easy, easy,” she begged, and I stopped to let her get used to it.

She blew out a few breaths, and tried to relax. I slid in just a bit more. Her pussy was now nicely lubricated, and I found I could go all the way in. She seemed to relax. “OK, keep going.” The rest of it was as if it were in slow motion. I moved in and out gingerly, but my mouth was in constant motion, kissing her lips, her eyelids, her forehead, bending my head and kissing her nipples, all while supporting my weight with my arms so she wasn’t crushed. Too soon, it seemed, I climaxed and my first orgasm unloaded a huge amount of sperm into her.

I eased myself over onto my side, so as not to be dead weight on top of her. “I’m sorry, my darling,” I whispered, “You didn’t come. That was rude of me.”

“I was just nervous about my first time, don’t worry.” Her tiny hand began to manipulate my manhood, bringing it back to life. “Let’s see what happens in round 2.”

The second time, my love came three times, one after another, like compound interest – the third was like a nuclear explosion.

Afterwards we cuddled for a bit, then I saw it was 12:15am. “Oh”, I whispered, “The time. I have to go.” I sat up, turned, and put my feet on the floor. Then I felt Katie’s two arms wrap around my waist, and her titties rubbing on my bare back. Hot breath and kisses coated my nck.

“Please,” she pleaded, tearing up as she said it, “Don’t go. Not yet.” Pulling me back down onto the bed, she lay her kisses up and down my chest, her tears falling from her cheeks to my pectorals. The beast awakened in me.

This time I was not gentle; she had awakened my inner caveman, and I took her. She responded in kind, our third coupling was raw animal passion, ending in nearly-simultaneous orgasms.

Afterwards, the two of us covered in sweat, I spooned with her in her bed until her breathing was deep and regular.

Gingerly, I eased out of bed and stood. “Please don’t go,” I heard her murmur in her state of half-sleep. I almost didn’t…but then another part of my brain reminded me Momma was waiting. I put my shirt and slacks back on, and grabbed the bloody towel off the floor as I left.

Tuesday 2:30am

I quietly let myself in Momma’s front door. The house was dark; I tread softly across the living room towards the stairs. I suspected she had fallen asleep upstairs. I heard a click as a lamp came on and illuminated Momma, stretched out across the sofa in her nightgown – THE nightgown – the one she was wearing when I dry-humped her. The crusty spot above her crotch from my seed was still there, four and a half years later.

I threw the bloody towel at her. She had been half-asleep, and as she sat up her tousled hair looked like she had already been fucked. My sore cock started to stiffen. She looked at the towel, and threw it on the floor in disgust.

“So much for midnight,” she said, reaching around and scratching her ass. A small glass and bottle of brandy was on the end table and she poured herself a shot, knocking it back and just as quickly pouring another.

“You got a head start this afternoon, stop complaining,” I snapped back. “Besides, you did say the shift end time was at my discretion. How often does a man get to fuck a virgin?”

Momma knocked back another drink. “It’s over-rated, you ask me,” she replied. “Your daddy didn’t think much of it. There was no romance. He kissed my titties a couple of times, spit on his cock, and in he went. It hurt and I bled. Took us a couple more fuck sessions before I started to enjoy it. Your father was such a cheating bastard I almost wished I hadn’t.” Momma poured again and gulped down her third drink.

“Well, Katie thought I was incredible,” I said in my own defense.

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