Crazy Tall and Pigtails Ch. 11

"No," I squeaked.

Anna repositioned herself and took me back into her mouth. She took her time getting my cock wet before pushing me to the back of her throat. She reached the part where Megan would normally choke and held there for effect. When she was ready, she opened her mouth a little wider and seemed to swallow my cock whole. She pushed down hard and every inch passed into her throat until she could lick my balls and bury her nose in my pubes. Her throat squeezed me like a soft wet hand.

"Oh, god," I moaned.

"Anna, that's incredible," Megan said, bending to look closer. "I can see you neck bulging out. How the hell do you do that without gagging?"

Anna pushed down even more before coming off my cock. Her saliva acted as a string back to my cock, which she quickly caught with her hand and applied to my dick. She gasped slightly before replying to Megan.

"Takes a lot of practice, but you need to overcome your gag reflex. Once you learn to do that it's a matter of breathing control, learning to swallow with something huge logged in your throat, and working your tongue. I'm sure if you practice enough, eventually you'll be able to handle this huge cock too. Watch me again."

Anna positioned herself and took me all the way with only a slight pause this time. Her throat muscles rippled on my cock and the sensation was unbelievable. Her tongue licked my nuts and saliva dripped from her mouth onto my sack. She stayed down for what seemed an eternity before pulling off. She gasped for air.

"That's fantastic! I don't think I'll ever do that as well as you," Megan exclaimed.

"Well, I've had a lot of practice with many smaller cocks too. David's is glorious, but hard to learn on for you. Just keep trying and practice with smaller toys like I said. Now you try it. Try to relax your throat and attempt to swallow down on his cockhead like you're trying to gulp down a huge pill," Anna instructed.

They switched positions again and Megan got to work on my cock. She tried hard, but each attempt at taking me into her throat failed short. Her gagging and coughing became more pronounced with each harder effort. Soon she just sat back and tried to catch her breath and relax her tortured throat.

"I can't do it," Megan reluctantly admitted and I knew it bothered her. She was such a competitor. I think she also wanted to impress Anna.

"Good try. Keep it up, but I think you've earned a rest. Why don't you switch places with David?" Anna offered.

"What? But we haven't gotten him off yet. What are you thinking?" Megan queried.

I was feeling anxious myself. I'd been close to cumming several times and been shut down by Anna's talented hands. 'What did Anna have in mind?' I wondered.

Megan reluctantly replaced me in the middle of the blankets. I moved off to the side as best I could with my cock like a pole in front of me. Megan and I exchanged questioning looks but complied.

"Megan, have you ever been with a girl?" Anna asked.

"No...I'm not sure I'd like that," Megan said.

"Just relax," Anna replied. "David, let's get her undressed."

With Megan's consent I helped Anna remove Megan's clothes, still wondering where this was going. Megan didn't seem to mind being naked in front of Anna or me, but she did look around again to make sure we were still alone. I did too.

"David, why don't you kiss the beautiful girl in front of you," Anna stated.

Anna had moved between Megan's legs and Megan nervously looked down her body until I blocked her view by kissing her moist lips. I slid my arm under her head and let her rest back. She kissed me back, but her attention seemed focused below with Anna.

"What a pretty pussy," Anna said.

I glanced down to see Anna parting Megan's labia and exposing her clit. Megan looked down too.

"What are you going to...?"

"Kiss her, David," Anna commanded. "Play with those cute tits."

I did and moved my left hand to caress Megan's perky mounds and cute small nipples. Megan moaned a little, but I wasn't sure if it was something I did or Anna. I knew Anna wanted me to distract Megan and I tried my best. At first Megan's kisses were almost nonchalant, but that didn't last long. Soon, she pushed back into my mouth and her tongue fought for supremacy.

I couldn't see what was going on with Anna, but I sensed it was starting to feel good to Megan. She stiffened and moaned into our kisses. Her hands started to pull me closer and she reached for my still stiff cock. I shifted to allow her an easier reach to me. When I did, I briefly glanced down to Anna.

Anna was working a finger into Megan and swirling her tongue in teasing circles around Megan's clit. Anna's skill wasn't just with cocks; she had obviously sucked plenty of pussies before too.

"Oh, god," Megan moaned as I returned to kissing her.

Anna and I attacked Megan with me on top and her on bottom. One finger became two in Megan's pussy and I started sucking on Megan's wonderful tits. Anna, Katie, and even Penny had bigger tits than Megan, but hers were delicious and her nipples grew incredibly stiff like erasers. Her tits were small, but they were sensitive and I loved sucking on them. Megan kept my cock happy too as we went back to kissing.

Megan started to groan loudly into my kisses. I stopped kissing her for a moment to look back and see Anna sucking her pussy. Megan looked down too, and her groans increased.

"Oh, Anna...please...suck it...please."

Obviously, Megan's early reluctance to have sex with a girl was gone. Anna had two fingers working inside Megan and we both watched as she sucked directly on Megan's clit.

"Oh, fuck," Megan groaned and threw her head back on my arm again.

I resumed kissing her even as she focused on what Anna was doing to her. I could feel Megan stiffen even more and her moans were even louder. She started to tremble and shake. I shifted most of my attention to her cute tits while Anna brought her closer to orgasm. Within a few more minutes, Megan was groaning aloud.

"I can't believe it," Megan gasped noisily.

Megan started to shake a lot and soon sucked in air as her pussy exploded against Anna's mouth. Megan's hands held my head hard against her breast.

"I'm cumming," Megan screamed way too loud.

Anna ate Megan's pussy through her orgasm until Megan began trying to squirm away. Her clit must have been over-sensitized as her climax tore through her and then waned. Her shaking body matched the groans escaping her lips.

Anna said to me, "Come here, David."

I stood and moved to her with my cock swaying before me like a flagpole. I was about to kneel by her, but Anna grabbed my cock and pulled it to her mouth. She pulled my hips to her and used my cock to face-fuck herself. Soon my cock was sloppy with her saliva.

Megan had just been laying there watching Anna face-fucking her mouth and recovering from her orgasm. She watched as Anna stopped sucking me and turned me to get between Megan's legs.

"Fuck her, now," Anna commanded.

I got down between Megan's splayed legs and looked at her inviting pussy. Her labia were parted and moisture glistened in the moonlight. Her little gash looked so small and vulnerable. I looked up into Megan's eyes even as I got into position. I wanted to fuck her badly, like Anna wanted, too, but I still needed Megan's approval.

Megan looked at me getting ready between her legs. I couldn't believe this was all happening. It was happening just like Anna had said, even predicted. She'd somehow orchestrated this whole thing and here I was aligning my cock with Megan's little pussy. I wanted to be in her so bad. Would she let me?

I almost signed audibly as I watched Megan nervously nod her approval to me. Looking down, I slid my cock along the slickness of her moist gash. It took a second in the very dim light, but I finally found the little gateway to her womanhood. As I positioned myself for the first push, I glanced up at Megan once more.

"Fuck her with that big cock," Anna implored.

"Go slow...you're so big," Megan said fearfully.

"I will," I agreed.

Using my knees for leverage, I slowly eased forward instead of pushing hard. Megan stiffened beneath me as my big cockhead tried to open up her pussy. The tiny opening resisted the intruding dick until I applied more pressure. Megan let out an audible gasp when I finally broke through inside her.

"Oh, god. Dave, go easy," Megan groaned with her hands pushing against my hips to try to prevent any sudden push.

I gave Megan a moment to get used to the initial entry of my cock into her. Then still applying the same level of pressure, I pushed forward again. Her pussy resisted every fraction of an inch, but eventually expanded to accept my intruding cock. Inch by slow inch her wet pussy allowed my large dick to penetrate deep into her. It seemed to take forever, but eventually I could feel the head of my dick touch up against her cervix.

"Oh, geez," Megan moaned. "You're splitting me apart."

"God, it's so hot watching you force your giant cock into her tight pussy," Anna murmured softly.

Giving Megan a moment, I slowly pulled back about half way before pushing forward again. Her pussy felt incredible on my cock, and so tight! Megan's hands were straining to push me back while still allowing me to continue. I started to develop a slow and steady rhythm, drawing my dick in and out of her. Her pussy slowly began to lubricate even more, allowing faster movements.

Anna had moved alongside Megan and her hands caressed us both. I felt one hand behind me rubbing menacingly around my balls. I could see her other hand tweaking Megan's closest nipple as she talked to her.

"Doesn't his big cock feel wonderful?" Anna encouraged Megan.

"He's enormous," Megan gasped. "It feels like a telephone pole inside me."

"She can take it, David. Give it to her...she'll love it," Megan instructed.

I slowly increased the speed at which I fucked Megan. She took everything I gave her and even started to pull somewhat instead of push with her hands on my hips. Anna sucked on Megan's nipples as I buried my cock within her. Her clasping walls felt like a slick narrow tunnel as she accepted each thrust.

"Oh, god," Megan moaned, but with distinct pleasure this time.

"She's loving it, David. Fuck her good. Make her cum hard," Anna encouraged.

"Urgh...shit," Megan gasped.

My dick probed Megan's pussy with each deliberate thrust. I was fucking her hard now, urged on by Anna's hand on my balls, and Megan's groans beneath me. In no time, I was pounding her into the sand beneath the blanket. The difference now was her thrusts were meeting my own.

"Oh, my god."

"She's loving that fat cock, David."

Megan's pussy had stretched quite a bit to accommodate me and I could now fuck her faster and deeper on each inward stroke. Wet squishy sounds filled the air over and above the gentle crash of the waves. Anna's attention to Megan's breasts only heightened her delight. My cock was hard as a gun as I drove into her.

"Oh, shit...I'm going to cum...fuck...I'm cumming," Megan howled.

I hoped no one was around to hear her shouts, but I didn't bother to look. I was enthralled with the intense pleasure coursing across Megan's beautiful face. Perspiration began to form on both our bodies. My ass was a blur now as I fucked her with nearly everything I could muster. Her clinging pussy accepted everything with its own wanton abandon now. I could feel my nuts preparing to pump my seed deep into her exquisite pussy.

"Cumming," Megan shouted. Fuck me harder, Dave. Don't stop!"

I wasn't about to. Anna stopped rubbing my balls and concentrated on both of Megan's tits. Her fingers pulled hard on the slender girl's nipples and kneaded the soft flesh around them. Between my cock drilling repeatedly into her stretching cunt and Anna's torturous fingers and mouth, Megan didn't stand a chance. Her back arched and she expelled whatever air she had left in her shouting lungs with one final scream.

"Ahh," Megan yelled.

I could feel her trembling with her orgasm beneath me. I was getting close to release too, and fought to get there. That is until Anna grabbed my balls and pulled them away from my body. She did it with such force I nearly came out of Megan's pussy. I tried to keep fucking Megan, but the restriction Anna's hand had on my balls lessened my movements and slowed my need to cum.

"Anna...geez," I groaned aloud.

"Save some for me, David," Anna commanded.

When Anna knew she'd backed me down enough, she let go, and I managed to fuck Megan until she collapsed like a limp rag doll on the blankets. Her climax had been very intense and as it left her it sapped her remaining strength. I had just finished the last few slowing strokes into Megan's splayed and limp body, when Anna sprawled on the blankets right beside her.

"Oh, fuck...I'm so ready for you to fuck me after watching her cum," Anna declared. "Get that fabulous cock in me, David."

I pulled free of Megan and she moaned lightly, but didn't open her eyes. Shifting quickly over to Anna, I decided to fuck her hard and fast, which is what I figured she wanted. I was right and she howled with bliss as I sunk the full length of my cock into her with one thrust. It helped that Anna's pussy was soaking wet. She had gone the whole night with us teasing and making love to Megan, and her pussy was on fire with its own need.

"Yes...Oh, drill me with that big man-meat," Anna directed. "God, I'm so hot for your cock."

The moments we spent switching women and pussies had allowed me a modest amount of time to recover. My desire was heightened by the need to give Anna the hard and fast fucking she so needed. I pounded her pussy with a vengeance for stopping me from cumming before. I wanted to show her the dominance I knew she loved. I'd bury my cum deep inside her core.

Anna must have been super-charged, because after only a few minutes of intense fucking she climbed the ladder to her release fast. I was right there with her as my cock surged inside her and pounded her ass into the sand. Megan stirred slightly and actually got to one elbow to watch us as my cum began to boil.

I was right in sync with Anna, and she screeched with delight as the bliss consumed her. Her hands gripped my sides in a near death grip. Her body shook and struggled to remain in rhythm to fuck back into my thrusts and extend her pleasure. I watched her ecstasy-chiseled face as my nuts began to spew hot cum-lava deep inside Anna.

"So good...oh I so love your cock," Anna wailed.

I glanced over at Megan as my dick erupted inside Anna. My prostate felt like it was emptying completely and turning inside out. The intensity of the orgasm made my cock spasm repeatedly in her. Wave after wave of delicious pleasure drove me nuts as my balls actively pumped seed into Anna's doubly soaked cunt. Our combined juices flowed down the crack of her ass onto the blankets as I finally stopped fucking her. I collapsed atop her before rolling to the side and ending up in the sand. My wet back held the sand like it was sandpaper.

No one spoke for quite some time. Eventually, the sand on me felt nasty and I had to get to the water and wash it and the sweat off of me. I got up and stumbled towards the water's edge. I didn't even care or realize I was butt naked. However, I did manage to look both ways and was satisfied no one was coming up the shore for a late night walk. Despite this, people in the houses immediately up from the beach could have seen me in the moonlight and probably realize I didn't have a suit on.

I was standing knee deep in the water when Anna and Megan surprised me by joining me. Both were equally nude as they stood next to me in the water. Despite the recent fucking, they both still looked gorgeous. Their nipples were hard and ready for more as they stood waist deep in the chilling water. The thought occurred to me, 'Could I go again and fuck them both one more time?' It was getting late though and Anna had to leave early the next morning. We would be packing and leaving too. 'What a shame,' I thought; I had just fucked Megan for the first time and I might be leaving before getting another chance.

After playing in the water with the two of them for a while, we made our way back to the blankets. They were half covered in sand and a huge cum stain wet one of them. I'd have to worry about that in the morning before we packed. We donned our suits and clothes and headed back along the beach. Two minutes into the walk we came upon two older men fishing in the surf. They eyed us up and down as we walked past. One said, "Nice night, huh?"

"Yes, very," Anna replied back with a mischievous smile.

I wondered if they heard anything or whether we were far enough down the beach. Sound carries at night, though. The look one of the guys gave me made me think he had, but it also made me think he felt I was the luckiest guy in the world. The two beauties flanking me on either side were both holding onto my arms.

Anna and I walked Megan home. Her parents would have long since left my house and probably be wondering where she was. I was glad her dad didn't come looking for her. After Anna and Megan said goodbye like long lost friends, Anna hung back on the dunes as I walked Megan the last few steps to her door. She turned to me as we reached it.

"That was the most unforgettable night of my life," Megan declared with a sweet smile.

"I'm glad you liked it," I responded.

"I never would have scripted it that way," Megan stated. "I mean, our first time together."

"Me neither."

"Anna can be quite convincing, can't she?"

"Very much so," I agreed. "You have any regrets...?"

"Not a one," Megan said quickly and cutting me off. "I'd do it again, and I want to with you soon."

"No more three-ways?" I said bemused.

"I wouldn't mind, but next time I want you all to myself."

"Me too."

"Will I see you tomorrow before you go?"

"I'll try to make it to the beach early enough for us to catch some waves."

"I'd like that."

"Me too."

"Dave?"

"Yes...?"

"How is this going to work?"

"I don't know...but I know I want it to."

"Me as well. Call me when we're back home?"

"You know I will," I concluded.

The kiss that followed with Megan was so passionate and long, I worried Anna might be jealous or get mad waiting. We finally parted and Anna and I walked back home. The first half of the walk was in silence.

"David?"

"Yes?"

"She's wonderful."

"Yes, she is."

"All I ask is you come to me once in a while, old friend."

"I'll try."

"Promise me...I can square it with Megan, you know I can."

"I'm a believer, after tonight. I bet you can do anything you want."

"When it comes to sex, I get what I want and then some," Anna said tossing her head back with a laugh.

"You do at that. Will you and Penny ever settle down and hang up your pigtails?"

"Yes...I think so...but I have a ways to go before I'm ready for that. Even then, I think my man will have to appreciate the experiences I've had and want to see them continue."

Despite being dog-tired, I couldn't fall asleep that night. My mind was racing too fast. Anna was just in the other room and one side of me wanted to crawl into bed with her and fuck her again before she left in the morning. I actually didn't think she'd mind and was probably hoping I'd try. However, my thoughts mostly lingered on Megan. I couldn't believe the evening had gone almost as Anna predicted. She'd gotten Megan and me together, to fuck on the beach with her there. She was truly a gifted manipulator of people, sexually anyway.

My thoughts remained on Megan. I didn't want to do anything to screw up the budding relationship we had started and then developed with Anna's help. It seemed, though, that the commitments I'd made to Katie and Anna for additional sexual encounters before going off to college were incompatible with my relationship with Megan. My mind tortured with the idea for several hours before sleep took me. How could I put Megan first and still fuck Katie and Anna? I even wanted one last shot at Monica and Penny, I realized.