The First Timers Club Pt. 08

"I'd met this woman, this amazing muralist named Valentina, several years prior through some mutual friends and I knew she was gay. I called her one day and asked if she'd meet me for coffee and I just opened up to her about everything. I told her about my attraction to girls when I was growing up and about my troubled marriage and how I didn't want another man in my life if I ended it with Jared and...I guess I just needed to talk to somebody who would understand what I was going through because she'd gone through it too."

Denise stroked Courtney's temple and softened her voice. "We talked for hours that day at the coffee shop. She was older than me, but I found her to be so elegant and feminine and funny and charming. We ended up back at her house and we talked and talked and as night fell, I found myself in her arms, just like this."

Denise leaned over to put her face just a few inches from Courtney's. "She looked at me, the way I'm looking at you now, and she smiled this beautiful smile that took my breath away and she asked if she could kiss me. Just like that. No hesitations, no beating around the bush, no awkward apologies. She just asked and I said yes and it was the most life affirming kiss I'd ever had because I knew right then who I was and what I wanted."

Courtney stared up at her, wide eyed, her breathing slow and shallow. Denise smiled her gorgeous smile at her.

"Can I kiss you, Courtney?"

Courtney hesitated only a moment. "Yes."

Denise caressed her face and pressed her lips to hers and kissed her, softly. Courtney reciprocated, opening her mouth to accept Denise's tongue. I stood and motioned for Brittney to come with me. I took her hand to lead her outside onto the balcony.

She waited at the railing to gaze out at the light of the city while I closed the slider behind us. She looked back over her shoulder and swayed her hips a little, and I moved behind her, putting my hands next to hers on the railing. When I pressed my body against her back, my stiffening cock nestled between her soft cheeks and I felt the rubber base of the butt plug through the soft Morino wool of her sweater dress. She giggled softly when I discovered it.

"You look so beautiful tonight," I said softly as we looked upon the city below. Brittney took a deep breath and sighed.

"I never knew that about Courtney," she said after a while.

"Does it bother you?" I asked.

"No. Not at all. I love her and want her to be happy," she said.

She moved her hips to rub her ass against my cock, and I put my arm around her waist and nuzzled the back of her neck.

"I kissed a girl once," she said, much to my surprise.

"Tell me about it."

I moved my hand to cup one of her breasts and gave it a gentle squeeze.

"Ash and I went to a band competition and there was this girl from one of the other schools and we just hit it off. Later, she took me into the bathroom and we started making out but someone saw us. She was embarrassed I think, and lied and said I kissed her, even though she's the one who kissed me first. Then, after that, everyone started calling me a dyke and a lesbo."

As she spoke, my anger began to simmer, but I tamped it down. One more finger to break.

"Did you like it?" I asked, then clarified, "The kiss, I mean."

She put her hand over mine and ground her ass against me, breathing out a long sigh.

"I don't know," she said. "I never really thought about it much before tonight. I think Denise is very pretty and sexy and all that, but I'm not sure how I'd feel if she asked to kiss me."

"Would you let her?" I asked, kissing the back of her neck.

"I think I would," she said after a long pause. "Just to know what it felt like."

"Does this feel good?" I asked when I moved my other hand to her pussy and massaged it through her dress. My cock strained against my pants and felt like a fleshy bar of iron

She reached up to hook the back of my neck and breathed a satisfied moan. "I want you to fuck me right here on the balcony," she said.

"I will, but later. Did you get a chance to see my bedroom earlier?"

"No, I missed it."

"Come on. I'm dying to show it to you."

I held her hand and guided her back inside the apartment. Denise laid on top of Courtney as the two kissed passionately, their hands moving over each other's bodies. They paid us no mind as we walked past them to my bedroom. Brittney thought to close the door behind us when I didn't, but I shook my head.

"Leave it open," I said. She glanced down the hallway, but I pulled her further inside. "Take it off."

Her wool dress crackled with static electricity as she pulled it over her head, and I realized that she actually didn't have pantyhose on underneath. What I'd seen had been the bottoms of her stockings. A black garter stretched over a pair of black thong panties, and a black satin bra completed the set.

"Oh my god," I said, and held out my hand to pull her in front of my dressing mirror. "Look at yourself, Brittney. You are so fucking sexy, do you know that?"

She appraised herself in the mirror, then reached across her stomach to hold her arm. "I'm too fat," she said.

"No you're not."

"Yes I am. You said so yourself this morning. I'm disgusting."

Fuck. "I'm sorry I said those things to you, Brittney, because they weren't true, okay? I only said them to trick you, but I took it way too far and I shouldn't have done that. The truth is, I think you're one of the most beautiful girls I know."

She stared at me through the reflection in the mirror with a dubious expression. "I know you're only saying that to make me feel better, but you don't have to do that, okay? I have eyes. I can see how fat I am. "

"You've got curves and they're fucking sexy as hell. You're like a work of art that I don't ever want to stop looking at. Did you see the way men looked at you yesterday?" When she nodded, I asked, "Do you know why they looked at you like that?"

"Because they've got low standards," she said under her breath.

I couldn't help but cough out a laugh. "No. It was because they were mentally undressing you and imagining this body."

She still seemed unconvinced, but she dropped her arm to her side. Although she walked a little taller these last couple days, her posture still communicated self-consciousness and timidity. I looked at her feet and noticed that she wore flats.

"How come you didn't wear heels?" I asked.

She turned to look at me directly and it was her turn to laugh. "I already stand out like a sore thumb," she said. "If I wore heels, I'd look like a freak!"

"No you wouldn't. You'd look like a goddess. Do me a favor. Stand up straight." I put my hand on her chin and said, "Lift your head up and put your shoulders back." I put my hand on her butt to push her hips forward. "Tilt your pelvis forward, like you're trying to stick your clit into a wall socket."

She giggled at me but indulged my odd requests. Standing up straight, she'd gained at least half an inch in height.

"Look at yourself now," I said. "You look more confident. You look like a bad ass bitch." She blew a laugh from her nose and tried to stop from smiling but flinched when I put my hand on her stomach. "See how standing tall flattens your stomach. Turn to the side."

She did and examined her profile. She rubbed her belly, which barely protruded. Then she reached back and felt her ass.

"Let me do that for you," I said, sliding my hand down her back and over the swell of her ass, to the cleft between her butt cheeks. Her thong laid over top of the base of the butt plug. I took hold of it and tugged it gently. Her eyes closed and her lips parted.

"I bought an enema bulb today," she said.

"Mm, good. Did you use it?" I tugged a few more times.

"Of course," she said between breaths. "I haven't eaten anything all day either."

"You sound exactly like someone who wants to get fucked in the ass."

"Because I do. I want you to double penetrate me again, but I want your cock in my ass this time."

"Did you bring the dildo?" I asked.

"It's in my purse."

I unclipped her garter and peeled her thong off, noticing that she wore a pad instead of a tampon, then reattached the garter to her stockings before unhooking and taking off her bra.

"I'm going to fuck you like this," I said, slipping into a dominant role. "Get on the bed and pull your legs back."

Her eyes moved to the open door, but she got onto the bed and pulled her knees back to her shoulders. Her waxed pussy still looked perfectly smooth, her plump outer labia a light rouge color, her small, delicate lips perfectly pink. While I massaged her clit, I slowly extracted the butt plug, and her eyes shuttered and she breathed out a gasp when she'd finally expelled it. I pushed three fingers into her ass before she fully closed up and her eyes shot open.

"Oh god!" she cried and her eyes moved once again to the open door.

"What's wrong?" I asked. "Why do you keep looking over there?"

"Nothing," she said quickly. "I just don't want to bother them."

"Don't worry about them. They'll be fine." I twisted my fingers in her ass and pushed them inside as far as I could. They slid in with only a little resistance. "This is good," I said. "You're nice and loosened up."

I found her purse on top of the dresser and retrieved the dildo from it.

"Did you bring the lube?" I asked, and her face fell.

"Oh no! I forgot it."

"That's alright. I'm pretty sure I have some. Don't move an inch, I'll be right back."

In the bathroom, I looked through the cabinets until I found my little cubby filled with oils and lotions. The blue-capped bottle stood out from the rest. When I returned, I held it up to her triumphantly.

"It's silicon based," I said. "Buttery smooth. It's going to feel great in your ass. But first, I'm going to eat your little pussy till you cum."

With three fingers in her ass to keep it loosened, and my thumb in her pussy, I attacked Brittney's clit, licking and sucking on it relentlessly until she bucked her hips beneath me and let out a barely stifled cry. When I lifted my head, she moved her eyes from the door to mine.

"Didn't I tell you to stop worrying about them?" I asked.

"I'm sorry. I can't help it. I'm just nervous."

"About what?"

"About her seeing me," she said.

"Who? Denise?" I asked. When she nodded, I said, "I fucked you in front of the others before. Why would that be any different?"

"It was my friends then," she said. "I just...I don't want her to see me."

"Why not?"

"Because, I'm hideous." she said quietly. "She's so gorgeous, and I don't want her to see how big and fat and ugly I am."

"You're anything but, sweetie," Denise said from the doorway. Courtney stood next to her looking dazed in a sexy panty and bra set, her black party dress missing in action. "Mind if we share the bed?" she asked me.

"You know I don't," I said.

Denise pulled Courtney into the room and pushed her onto the bed, then reached back to unzip her jumpsuit. When the straps cleared her shoulders, the satin garment slipped effortlessly from her body and puddled on the floor. She stood fully undressed, save for a tiny pair of panties.

I'd seen Denise's naked body dozens of times, but it never failed to take my breath away, and not because her body was perfect. Far from it. Denise worked out often enough, but she still had a thick middle section, and the wide hips and broad ass of a middle-aged mother.

But those were minor issues compared to her skin. Her genes had cursed her with tight, inelastic skin, and she wore the unforgiving battle scars of motherhood. Web-like stretch marks, long faded and appearing like burn scars, marred her belly, her hips, and the sides of her ass. Her large breasts, though full and well-shaped with only a slight sag, also bore the thin, pale lines that carried from the top of her chest almost to her nipples.

What always impressed me about her, though, was her poise and the unabashed attitude she had about her body. She loved the way she looked, even incorporating her stretch marks into her tattoos, and she loved being naked in front of other women and that made her a hundred times sexier than any Spring Break beach bunny in my estimation.

Without so much as a glance in our direction, Denise climbed onto the bed, pulled off Courtney's panties, and went down on her. They kept to their side of the bed, leaving the other open and available for us to use. I turned to Brittney, who gawked as her friend had her pussy eaten by an older woman they'd only met the day before. When she noticed me looking at her, her eyes slid away.

"You can watch," I told her. "She won't mind."

"Shouldn't we leave?" Brittney whispered.

"Please don't," Denise called out from between Courtney's legs. She turned to look at Brittney and said, "I really want you to stay so I can watch him fuck you." Then she kissed her way down Courtney's thigh and lapped at her pussy.

Brittney stared at me, astonished.

"Is that okay with you?" I asked her.

She turned to watch again when Courtney tossed her head back with a small cry and pushed Denise's face into her crotch. I watched Brittney's cheeks and chest flush and redden. When I began to remove my clothes, she returned her attention to me and her eyes drifted to my stiff cock.

"Brittney," I said, and her eyes moved to mine. "Come here." She stepped forward and I kissed her, then turned her around. "Put your hands on the edge of the bed."

She did as I told her, turning her head to watch me squirt a large volume of lube into the palm of my hand, which I used to coat the shaft and head of my cock. Then I stepped behind her and slapped her ass. Not too hard, but firm enough that Courtney turned her head at the sharp sound. I slapped Brittney's other cheek, a little harder, and she stifled a cry.

"Too much?" I asked. She looked back over her shoulder and shook her head. When I spanked her again, harder still, she cried out.

"Ah!"

"Too much?" I asked again, and she still shook her head. The next slap caused her to dance on her toes.

"Too much!" she cried.

I dialed it back and slowly spanked her ass, alternating between cheeks, letting the sting of the last slap fade before moving to the next. Brittney's ass cheeks turned pink and then red, and each slap ripped a fresh cry from her lips.

Denise brought Courtney to a rapid orgasm that caused her eyes to fly open as she cried out. She pulled Denise on top of her and attacked her mouth, kissing her forcefully.

"Would you like to go down on me?" Denise asked her, and got her answer when Courtney pushed her backwards and sat up to take off her bra. Denise pulled off her panties, then leaned back, braced on her arm, and spread her legs for Courtney. "Look at what you've done to me. I'm so fucking wet," she said when she dragged her fingers over her slit.

Courtney got onto her elbows and knees and moved her head close to Denise's pussy but hesitated to move any closer. Denise showed restraint and patience, allowing Courtney to study her pussy and gauge her willingness to eat it.

"It's okay," she said. "Just look at it, honey, and watch me while I play with myself. When you're ready, you'll know."

My state of readiness to fuck Brittney reached its own tipping point. I put my hand on top of her ass and pushed down. "Bend your knees a little," I told her, guiding her down until her anus lined up with my cock. Then I pushed forward to slowly ease inside of her tight asshole and began to fuck her.

"How does that feel?" I asked her, but she only whimpered in response. "My cock feels so good in your ass, baby. So fucking good."

And it did. The new lube allowed me to glide in and out of her easily, and her tight asshole clung snuggly to my shaft. Brittney had difficulty restraining her vocalizations, crying out or grunting every time I pushed my cock inside of her. When I looked up, I locked eyes with Denise.

"I love watching you fuck," she said to me while she masturbated. Then to Brittney, she said, "Tell him, Brittney. Tell him how good it feels to get fucked in the ass by his big cock."

"So good," Brittney cried, her words flowing and unrestrained. "I love it so much."

"Tell him to fuck you harder so I can see your beautiful tits swaying."

"Fuck me harder," Brittney cried desperately, and I increased the pace of my thrusts.

"Tell him to fuck your ass," Denise told her.

"Fuck my ass! Oh god! Oh god!"

Denise's lips curled into a satisfied smile and then she gasped when Courtney lowered her head to lick her pussy. The sight of Denise being eaten out by Courtney, and Denise's impassioned response, thrilled me and caused me to fuck Brittney's ass even faster and harder.

Denise put her hand on Courtney's head to guide her. "Mm...oh god, yeah. That feels really good. Suck on my clit, sweetie. Here, let me pull it back for you. There you go. Suck on it. Flick it with your tongue. Oh my god, oh my god, that feels so fucking good. Oh, god..."

I pulled my cock out of Brittney's ass and spanked her a few more times. Then I picked up the dildo and lubed it up.

"Lay down right here next to them and pull your legs back."

She didn't hesitate. She laid down next to Denise and pulled her knees to her shoulders. I stepped to the edge of the mattress and dragged her toward me until her ass hanged off the side of the bed. Then I pushed the dildo into her pussy and stuck my cock back inside her ass.

Denise tried to concentrate on Courtney's first attempt at cunnilingus, but she became distracted by Brittney's cries and screams as I double fucked her with my cock and the dildo. Even Courtney looked up a couple of times until Denise coaxed her face back to her pussy.

"Rub your clit, baby," I told Brittney after I took over the job of holding back one of her legs. She put her fingertips on the tiny nodule and quickly rubbed it as if she expected a genie to pop out. It took almost no time at all for her to orgasm, and her crying scream startled Denise.

I pulled both the dildo and my cock out of her and gripped her hair to pull her into a seated position at the edge of the bed. When I guided my cock toward her mouth, she put up her hand to stop me.

"Wait, what are you doing?" she asked.

"Putting my cock in your mouth, what does it look like?"

"But you just took it out of my ass."

"Did you clean yourself today?" Denise asked her and Brittney nodded. "Then it's fine. Your ass is probably cleaner than your pussy right now."

Best damned wingman I've ever had. Brittney looked at my cock with a skeptical expression, but it seemed clean. She took hold of the base and smelled it, then looked up at me.

"Are you sure it's really okay?" she asked.

"Give it here," Denise said. "I'll suck your cock."

She'd never offered to do that before. Ever. I looked at her and asked, "Are you sure?"

"I want to taste her ass. Now hurry up before I change my mind."

I didn't hesitate. I stepped closer to her and she took my cock in her hand to suck the head. I'd wanted to fuck Denise since the first day I'd met her, and I'd tried many times over the years. She'd always been polite about my advances, moving my hand away whenever I groped her in bed, either accidentally or on purpose, but she'd never once relented. That she'd agreed to suck my dick suddenly and out of the blue baffled me completely, but also thrilled me to no end.

I restrained myself from putting my hand on the back of her head or encouraging her too much, but I couldn't help the soft groans that escaped the back of my throat as she rolled her lips over the glans. After a few seconds, she lifted her head to talk to Brittney.

"Your ass tastes delicious, honey," she told her, then she gave my cock one last suck and said to me, "Go over there and fuck her gorgeous mouth with it. I want to watch that."