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"Like mother, like daughter," Colleen answered, sounding proud.
"Stop you two. If you keep that up, I'm not going to last two minutes."
"Poor baby. Two hot MILFs too much of a distraction?" Mom teased.
Colleen nibbled on my ear. "She's good for a beginner. I'm better."
I groaned. "Please. You're killing me," I whispered. "This is her night."
Mom leaned across me, blocking my view of Penny's actions with her tits in my face. I wasn't going to complain, chasing her nipple through her flimsy nightgown. When she got off me, I looked over and saw that Colleen was naked to the waist. Big natural boobs staring at me. Bigger than Mom and Penny. Maybe as big as Aunt Marie. Not as firm, maybe, but I wouldn't mind finding out. I couldn't help scope them out, huge friggin' nipples, as big as the end of my pinkie, standing tall.
Penny was sucking me, doing her best to avoid laughing. She pulled up, stroking me with her hand. "You both are horrible! He's mine tonight. You both have your own men." She was grinning as she said it, her eyes lively.
"Of course, Princess. All yours. That's a lot of man, are you sure you can handle it alone?" Colleen teased.
"Damn it, Momma! Yes. I can handle it."
"That's wonderful. Remember, if you need help, Alice and I are here for you."
"Behave Momma, or I'll make you watch from the chair." She grinned and took me in her mouth, sinking down, pushing, forcing my cock into the back of her throat. She gagged for a moment, then her lips slid down my shaft, her nose pressed against my pubes. She stayed there, looking at all of us. She pulled back, gasping. "See? I told you I can handle it. I'd like to see you do that, with something this big," she taunted.
I turned to Colleen. "Me too," I whispered, winking. "Like mother, like daughter?"
"My baby girl. I'm so proud of her. So much like her Mommy."
Penny went back to blowing me, and Colleen got up, leaning across the bed. Her breasts settled over my face, and I got my first taste of her hard nipples. She pulled away a little later, pausing to watch me, until my lips released her hard little nub, stopping to give me a quick kiss. "There, now we're even."
I looked over and Mom was naked. "Even?"
"We will be in a moment," she said, and I looked back to see her removing her nightgown. Fuck. She had a tattoo of a rose just above her bare pussy. Unfair.
"Penny," I warned.
She pulled up, and sat back on her feet. "Come on my face, Jeremy."
Releasing the Moms, I struggled to my feet, sliding my cock back between her lips, holding her head and fucking her mouth.
"Gentle, Jeremy," Mom warned. She was kneeling beside me, camera in hand, getting a closeup.
I was being gentle. As gentle as I could be under the circumstances.
I felt Colleen move up next to me, her hand between my legs, massaging my balls. "Give it to her, Jeremy. She can take it. Paint her pretty for us."
I groaned, pulled my cock out from between Penny's sexy lips, and erupted, a long stream of cum streaking her face from hairline to chin. Several more shots later, and she was a beautiful mess, her face covered in my cream. She had her eyes closed, smiling angelically. She slowly laid back on the bed, stretching out, her legs open.
"Practice me, Jeremy, while your Mom cleans me up."
Mom giggled. "That's a lot to clean up, honey. He got you good. It is Ok if your Momma helps?"
Penny grinned. "That would be perfect."
Mom handed me the camera. "Don't do her yet, baby. Get a couple of minutes of this. The Dads are going to love it."
I moaned, already hardening, as I watched both Moms lean over and start licking my sexy girlfriend's face clean. They were sweet and gentle, both of them, their tongues moving slowly, curling, scooping up my cream.
Colleen moaned adorably. "He's sweet. Jesus, I could do this all night."
"Isn't he? Marie told me he was," Mom told her.
"Your sister said that? God, that's kinky," Colleen whispered.
I had a great shot of it all, groaning when I saw the moms come together above Penny's lips, kissing each other. It was cute, a tiny little peck at first, until I saw their tongues, working, cleaning each other's mouth, battling for my cum. Holy fuck, that was hot.
"Open up, baby," Colleen said softly. Penny opened her mouth, and I struggled to avoid stroking myself when she licked cum off of her daughter's forehead, then stuck her tongue in Penny's open mouth. Penny sucked on her tongue. "Mmm, thanks Momma."
"There's more," Mom said, licking Penny's eyelids before slipping her own tongue between my girlfriend's lips.
Penny reached up and held my Mom's face in place, kissing her hard. "My two Momma's taking care of me," she sighed.
"Fuck," I groaned.
That got them all giggling. "I think he likes the show," Colleen said.
"I should warn you. I'm taking this out on your daughter's pussy in a few minutes."
Mom turned to me. "Don't even joke about it! If you're not gentle with her, I swear, you'll be cut off from everything." She wasn't kidding.
"Mom! Of course I'll be gentle. The first time. But we've got a long night ahead."
Colleen leaned over and kissed Mom, stroking her hair. "Trust him, Alice. Penny does."
Mom sighed. "I do. I trust him with my life. But I also remember what it was like."
I crawled around the bed, and pulled my Mom up to her knees, hugging her. "I'm going to make it perfect, Mom. I promise. Whatever it takes. I wouldn't hurt her for the world."
"I know, baby. It's a little scary, that's all."
I tilted her head up and kissed her, tasting myself on her lips. "Trust me, please?"
"Always," she said softly.
I reached over and grabbed Penny around the waist, lifting her easily and spinning her around on the bed, tossing her into the middle, making her squeal and laugh.
"Gentle!" Mom snapped, slapping me hard on the back.
"Jesus, Mom! You wouldn't know gentle if it walked up and smacked you in the face. I've seen how Dad is with you."
"Jeremy..." she whined.
"We're playing! Having fun. Shouldn't this be fun? Wonderful? When it comes time for the big show, we'll be as gentle as she needs. Now cool your jets, or you're getting banished to the Bad Mommy chair."
Penny and her Mom were laughing. "Someone's slacking off," Penny announced, reaching between her legs and slapping her pussy. "It's not going to lick itself, handsome."
I climbed between her legs, blowing a raspberry on her pussy, before going crazy on her. She was laughing hard, wiggling underneath me. The Mom's bracketed her, teasing her, playing with her tits. I couldn't help grinning. I came up for air. "God, Penny. I love playing with you. Fuck me for being an idiot and waiting a year for this."
She laughed joyously. "Come up here and kiss me, stupid. Then I want you to make a woman out of me."
I climbed up and kissed her tenderly. "You are so wonderful," I told her.
She smiled. "You ain't seen nothing yet. Once you've broken me in, I'm going to fuck your brains out."
I kissed her again, tasting her lips. "I love you, baby girl."
"I love you too." She stopped smiling, and looked into my eyes. Those beautiful big blue orbs, mesmerizing. "I think I'm ready," she said softly.
The moms went into action. I watched Mom pull out two full pillows. "Raise your hips up, Penny, this will make it easier for both of you." She slid the pillows under my girl, lifting her butt up, and tilting her pretty pink pussy up toward me. I gave her a quick lick before I was pushed away by Mom.
Colleen had a bottle of lube in her hand. "Pink? Is it any good?"
Mom nodded. "Miracle juice, slippery as hell, and it lasts as long as you want. Perfect for marathon sessions. You can borrow it, if you want to give it a try. I've got more."
Colleen was pumping the lube into her hand, and rubbing it into her daughter's pussy. Fuck. Much more of this, and I'd be shooting before I even got inside her.
"Condom, Mom?" I asked.
Penny spoke up. "I'm on the pill, Jeremy. We're good."
Mom looked over at Colleen. "Get him ready?"
She looked at Mom, then down at Penny. "May I?"
Mom nodded. "I can't. He's my boy."
Colleen moved over and I groaned when she lowered her mouth over my cock. She sucked me nicely, easy and slow, taking me deep in her mouth, her naughty MILF tongue active. I reached down and played with her tit. Yummy soft. After only a minute or so, she pulled off. "Jesus, Alice. He's huge, and hard as a steel rod. It's a lot for a first time."
Mom took the lubricant, and squirted it on my cock, rubbing it in. "She'll be fine, I promise." She leaned her head against mine, her breath warm against my ear. "Try not to hurt her too much," she whispered.
"I know, Mom. Kiss me for good luck?"
She smiled, and pressed her lips to mine briefly. She pulled back and brought the camera back up.
"Penny?" I asked.
"Now, please, Jeremy. I can't wait any longer."
I took my cock in hand, scooting forward on my knees. I pressed the head against her opening, rubbing it up and down. Mom was right, it was slippery as hell. Her lips parted, and I saw the bright pink of her insides. I pushed the head against her, and pushed.
I sat up a little higher, lining up again, and pushed into her. Harder. A little moan escaped her lips. I saw her mom was lying down next to her, eyes tightly closed, clutching her daughter's hand in hers. Her knuckles were white. My cock started to bend painfully.
"Ease up, baby," Mom whispered from beside me.
I pulled back and heard Penny sigh. Mom reached down and stroked me, nibbling on my ear lobe. "It'll be fine. Push hard, quickly, we just need to get the head in. That's the worst," she whispered.
I opened Penny with my fingers, then pressed the head up against her opening. I grabbed my cock a couple of inches back, to stop if it went in too fast. I leaned over my tight little virgin, pushing hard, feeling a little give. Penny was whimpering softly. I took a deep breath then stabbed forward. She cried out, and I felt my cock slide in a couple of inches.
I looked up, worried. She was painfully tight.
She was staring into her mother's eyes, only a couple of inches apart. "Is she Ok?" I asked softly.
Penny nodded slightly. Colleen looked over at me. "She's fine. Slowly now." I watched her brush a few stray tears from her daughter's cheeks.
Mom whispered in my ear. "Little nudges forward. Teeny tiny. Take your time."
I took her advice, rocking my hips ever so slightly, push, rest, push, rest. The tiniest pressure. It moved slowly, in small distinct increments. I'd make no progress for a few seconds, before sliding in another half inch or so. Penny gasped with each little bit of additional access. I looked down and was surprised I had almost half my length inside of her.
Mom gave me a squeeze. "That's enough for now. Back and forth slowly, but no deeper, Ok?"
I eased back out carefully, leaving the head inside. I didn't want to have to go through that again. Penny sighed, relaxing as I pulled back. I pushed forward, steadily until I'd regained most of my ground. Still ridiculously tight. She gave a soft whimper and I slowed.
"Don't stop," she said softly. "It feels good. Big, but good."
Thank God. Back out slowly, then back in again, a couple of seconds on the down-stroke. It was getting easier. I found myself developing an easy rhythm, about a full second in each direction, feeling her virginal tightness slowly start to give.
Mom was reaching down, rubbing Penny's clit gently. "A little bit deeper now, no more than an inch or so," she said softly.
At the end of each stroke, I started pressing a little harder. She was opening for me, letting me in. Mom stopped me with a couple of inches to go, her hand just above my cock. "No further than that, tonight. You're long, and you'll probably bottom out. Most girls find that uncomfortable."
I stopped with most of my length inside of my sweet girlfriend. I leaned over her, my face a few inches above hers. "Are you alright?" I asked.
She smiled tentatively. "Remind me to shove a two-by-four up your ass later, and I'll ask you the same question."
I grinned and she laughed, cringing a little. "Damn, Jeremy. Why couldn't you be human sized?"
"I'm not that big," I told her.
"Nine inches?" Colleen asked.
"A little over eight," I told her.
She shook her head. "Not tonight you're not. I've had eight inches. It didn't look like that."
I leaned over and gave her a kiss. "If I'm bigger than normal, you know whose fault that is, right?"
"Your Mom's?" she said, getting another giggle from Penny.
"You'll get yours," I told her.
"God, I hope so," she said, smiling at me. Her smile slipped away, becoming much more serious. She reached up and touched my cheek tenderly. "I'm sorry I was mean to you earlier. I couldn't ask for a better man for her first time. I can see why she's so crazy about you."
"Thank you, Colleen." I grinned. "I like your tits, by the way."
She gave me a loving slap, followed by a sweet little Mommy kiss.
"Ready for more?" I asked Penny, leaning down and chewing on her lips playfully.
"There's more?" she asked nervously.
"Not more cock. More fucking."
She took a deep breath and nodded. "Fuck me, Jeremy."
I got back on my knees, opening her legs. I'd slipped out about halfway while talking to her. I returned to stroking her slowly, all but the last couple of inches.
"Can I go faster?" I asked my mom.
She reached down and touched me. "Pull out to the edge a second."
I slid out, all but the head of my cock shiny with her juices. I was swollen up as big as I'd ever seen it.
Mom had the lube in her hand, and got me nice and slippery again. "Colleen was right. You're huge tonight. Hell of a time for you to get like this," she said, sounding almost irritated.
"Like this is my fault? I'm getting my first real fuck, with this gorgeous virgin, and two incredible sexy naked women helping and watching. If that wasn't bad enough, the MILFs are not just any Mommies, but mine and hers. Geez, Mom, we're lucky I've lasted this long."
"Um, down here, guys" Penny teased, "ex-virgin needs tending."
Mom patted my rear and give me a kiss on the cheek. "Faster now. Little bit at a time, until she complains."
I slowly picked up the pace, watching her reaction. After a minute or so, I had doubled it, at least, and it was getting easier. She was moaning softly, but it didn't sound like pain. My hands were caressing her thighs, hips, belly. She was so soft and smooth, her skin felt like velvet. I heard her first little love moans.
"Ok?" I asked, maintaining the steady stroking.
"It's good, sweetie," Colleen said.
Penny was squirming a little, biting her bottom lip. The moans were more frequent. I fucked her faster, still only three quarters of my length, making her whimper beautifully. It was feeling good. Wonderful. Earlier it had been too much work, too tight, too distracting. Now I was feeling her. I liked it.
Mom leaned against me, "Close?"
"Not yet, but it's getting better," I told her. "It hurt before."
"She can take a little more, a little faster. Tilt her legs back."
I lifted her legs, hands behind her knees, and pushed them back, halfway to her chest. I felt an immediate change, more pressure against the top of my cock. She gasped, trembling, a cute series of grunts escaping her talented lips, I slowed down to make sure she was Ok.
"Don't stop!" Colleen cried out.
Speeding up, I fucked her harder, faster. There was only an inch outside of her, and she was whimpering so sweetly it was driving me crazy. "God, Penny, you are so fucking incredible," I gasped.
Her calves were trembling, toes curled so cutely it hurt. She started whispering, a series of groans, and muted "oh's". She even squeezed in the occasional "God!"
"Steady baby, just like that. Give it to her. You've almost got her."
The pace was fast, but not out of control. I knew I could sustain it for a little longer. The feeling was magical, and I felt the pressure building down around my balls.
"Momma!" she cried out gasping, her legs stiffening.
"Harder," Mom whispered, reaching down and rubbing Penny's twitching clit.
Unbelievable. I was fucking her with my full length, balls slapping against her ass. I leaned over her, sliding her ankles over my shoulders, my arms outside them, supporting my weight, pinning them in place. I rose up on my toes, legs straight, slamming into her, pummelling that tight virgin pussy. Every stroke, long and full, my entire shaft driving deep. My full weight crashing down on her poor innocent pussy, crushing her. Mom was going to kill me, I was being anything but gentle. It couldn't be helped.
Penny was staring up at me in amazement, her eyelids fluttering, her eyes rolling back in her head for a few dick hardening moments. Her jaw started trembling, her lips shaking. Beautiful, kissable lips.
"MOM!," she screamed, her body tensing below me, thighs as tight as steel bands. Her pussy clamped down on my cock like a fist.
"Don't stop, Jeremy!" Mom gasped.
"Fuck," I groaned. "It's too good," I straightened, grabbing the front of her thighs, pulling her back against me on each stroke, gasping as I felt my imminent release. "FUCK!" I growled, slamming into her and feeling the rush of fluid up my cock, screaming for release, firing off inside her.
She was squealing, nonsense sounds, trembling, throwing her head around. She was bright red, from her pretty face, across the top of her chest and shoulders, down to between her tits. Colleen was holding her, trying to sooth her.
I didn't think it would ever end. For either of us. Every time I thought it was over, I'd feel another spasm, and push deeper inside her. I could feel myself touching bottom, but each thrust seemed to set her off again.
After what seemed like an eternity, I could feel it was over. For a few moments there, I had gone deaf, dumb and blind, my entire existence reduced to those few inches buried inside her tight velvet embrace. I was losing my hardness, to my infinite regret. I pushed deep, leaning over her, gasping. I never wanted to pull out of her. Never. Her pussy was pulsing around me, squeezing me, teasing me.
"Jesus," Mom whispered. "Sweet Jesus."
I slowly backed out, her tightness pushing me out the last couple of inches. I kissed her soft smooth calf, lowered her legs, and then crawled up next to her, pulling her into my arms. She clung to me, crying.
"Shh," I whispered. "I love you, Penny." I rolled onto my back, pulling her with me, her chest resting on mine, her head tucked into my shoulder. I was both exhausted and exhilarated. I tried to catch my breath.
She only cried harder.
I felt movement down below, and found Mom sucking me clean. She was very gentle, thankfully. I was ridiculously sensitive. It verged on the comical, her wonderful mouth holding my cock, while she kept that damn camera focused on Penny and me.
"What's wrong, baby?" I asked. "Did I hurt you?"
She was sniffling, kissing my shoulder. "Hurt me? It was perfect. I was so scared. I didn't want you to know, but I was terrified. I didn't think it could actually fit. All my fears came true when you couldn't get in me, and then that big push, tearing me open. God, that hurt so bad Jeremy! I can't remember anything hurting like that. I really thought you had torn me open. I had to be bleeding out. But I knew I couldn't be. My Mommas wouldn't let that happen."
I hugged her. "I'm sorry."
"Sorry? It was wonderful. So...so amazing. I thought I'd have to just suffer through it, try not to let it show, but then it started to feel good. Incredible. I was full, completely, all the way to the back, each nudge at the end like a jolt. Every nerve in my body going off each time you touched bottom. Watching you lose control over my pussy, hammering me, glowing above me, God!"