Anal Summer Ch. 09

"Well, over here we have these, a wide array of butt plugs from small (Judy extended her pinkie finger to illustrate approximate size) all the way up to Godzilla. Butt plugs are great because they are a hers-and-his toy."

That aroused and scared me at the same time. I didn't speak. Madison and Judy both looked at me. I had a look of fear on my face, causing both women to laugh.

"And these are what is known as anal screws. They come in in several styles of size, width, length, and hardness." The anal screws looked like giant drill bits with rounded edges. Judy continued: "The screw gets gradually thicker the deeper you screw it in to your partner's anus, for a more gradual, deeper insertion, with more comfort and finesse. Ben-wah balls are also good to enhance anal sex even though they are mostly used with vaginal sex and masturbation; you can definitely benefit from them while having anal."

"How?" Madison inquired.

"You put them in your vagina, and they stimulate you on the inside while he makes love to your rear end."

Those words almost made me come in my pants.

"Have you tried doing him?" Judy asked Madison in a matter of fact way.

Madison's answer was, "Not really," as she extended her index finger to silently illustrate that she had used her finger on me.

Judy smirked and gave a nod of understanding, then continued her sales pitch: "We have the equipment so you can do him. It's called a strap-on and..."

"We're not interested in that," I nervously interrupted.

"Speak for yourself," Madison purred in a low, sultry way, her beautiful lips curled in to a cute but devilish snarl.

"It's not gay if it's with a woman," Judy added in her soft, smokey voice, turning her attention to me as she looked straight into my eyes.

"Maybe it's something we can work towards... just not now," I said, ending the conversation on that topic.

That caused Madison to out an arm around me, across my back, her hand on my shoulder, softly caressing me in a reassuring gesture.

Madison went on to explain, much to my embarrassment: "He's just learning about his body and about intimacy and pleasure."

"He's so handsome. How old are you, honey?" Judy asked

"I'm 21," I answered at once, unsure if the legal age to be in the adult book store was 18 or 21, so I said 21 just to be safe.

A big grin came over Judy as she said to Madison, "Wow! Good for you, Mrs. Robinson! You must be getting lots of exercise!"

They both giggled. Here I was again being objectified, internally, a tiny bit hurt and yet I loved it, too.

Once they collected themselves, Judy introduced us to anal beads of different sizes and explained how they worked. She told me that they were also a hers-and-his toy."

I didn't say anything.

"You have a prostate that can be stimulated through your anus. If you had a butt plug in while you reached climax, it would intensify things for you."

I already knew this from having Madison and Margot do it to me with fingers.

"And anal beads will send you through the roof if she times it right and pulls them out slowly while you're coming."

When Judy said that, I almost came in my pants. As it was, I was pitching a tent and didn't even care any more if they saw it.

"I would love some of those beads. In fact, I will take all three sizes, and the first five sizes of butt plugs, too." said Madison, taking charge. Well, I had to say, it didn't take her long to make up her mind. Judy loaded the requested items into our shopping basket.

"What other interesting things can you show us?" asked Madison.

"There is a new item that just came in this week, and though I haven't used it, I love the idea of it." Judy said. She took us over to a glass showcase. This is a little pricey, but it's pretty awesome, she explained as she removed a small box labeled, "The Remote Lover." She explained: "This egg-shaped vibrator stays up inside of your vagina and is remotely operated by this little wireless control. He holds it and whenever he feels like it he can give you a buzz. He can start and stop the egg's vibration and change the speed, so if you are out at a party or at dinner somewhere, perhaps the opera, it's your little secret between you both. Any time he wants, he can remotely stimulate you...up to 300 yards away."

"We have that party after the regatta, " Madison purred to me, her imagination running wild.

This shopping expedition was getting her horny, too. "Yes, we will take it as well," Madison said.

"Okay... the regatta 'after' party? That's funny, we've had several couples in here talking about that," Judy chimed in.

We also stopped by the movies at the section marked "ANAL" and got three movies that I "wasn't allowed to view 'til later." Madison had picked them out as a surprise for me.

When we finally checked out, Madison had purchased two regular dildos and the "King Cock Double Penetrator" dildo, two anal screws, five butt plugs, three sets of anal beads, the "Studded Climax Plus" vibrator, the remote-controlled vibrating egg, a master set of ben-wah balls that included three sizes, "Caught From Behind" movies parts 1, 3, and 4, and finally, a big pump jar of silicone anal lube, its black label with white staccato letters seemed to scream out at you.

Judy rang us up, and the bill came to $317.50. Madison paid for it without so much as batting an eye.

I offered her some money, but she refused to take it. I had forgotten that Madison probably made that much money in five minutes.

Judy put our purchases in to two large, plain brown shopping bags. "Well, thanks for coming by. You have plenty of fun things to play with. Have a great night!" said Judy.

I was half hoping she would also jump in the bag herself and come home with us.

Once back outside the Freedom Book Shop," the hot summer air plus the sound of honking horns and traffic brought us back to earth. For a short time, Madison and I were transported to a world of open sex and pleasure. For the first time in my life I had fun shopping; it was like extended foreplay.

I turned to Madison, held her hand and said, "That was fun! Thank you!" and I meant it. I was truly grateful for this woman and her tutoring. There was no doubt sexually she was helping me become a man, and the curriculum was the most fun I had ever had.

Madison smiled and squeezed my hand scrunched up her shoulders in over exaggerated girlish excitement. "I know! I can't wait for us to get to my place so we can play with our new toys."

The walk back felt like forever with every step bringing us closer to the wild romp of sex, toys, and pleasure. When we arrived at Madison's condo it was close to 9:00 pm and the dusk was like a cloak shrouding the deviant activities that were soon to follow.

Once inside, we showered and slowly approached the bed. The brown shopping bags full of toys, mystery, and wonder awaited us there.

"What shall we play with first?" Madison asked in a soft, sexy whisper.

"Whatever you desire most," I answered. The truth was, I was looking at a buffet of everything I ever wanted and would be happy no matter what.

Madison didn't answer. Instead, digging into the bag and emerging with the silicone anal lube, she broke the plastic safety seal off of it and unlocked the dispenser pump. She pumped out a tiny amount and tested it by rubbing it between her thumb and index finger. Distracted by the quality and smooth lasting effect the silicone-based lube had, she almost mindlessly reached back and submerged her lubed finger in the trench between her buttocks and massaged the lube on to her sphincter.

Madison was so impressed, it was as if she had almost forgotten I was there. She wiggled and worked her fingertip into her rectum. It was an incredible sight to see, this gorgeous woman stimulating her own anus. I was there watching her, and my penis was like a concrete tower; my full testicles ached to be relieved of the semem that engorged them.

I was not at all upset that Madison had zoned out on me but aroused at the fact that anal sex was such an important part of her life that finding a better anal lube was a reason to lose track of the world for a few seconds.

"You naughty girl! Having fun playing with your asshole and not inviting me!" I said in a crude shameless way as I snuggled up and stood right next to her, my erection brushing her naked hip.

"Mmmm, this stuff is incredible!" And without another word and before I could react, Madison slid her finger out of her anus, stepped forward and retrieved the Studded Climax Plus vibrator.

I quickly removed the packaging and brandished it like a sword. "I have made a decision," I announced as I held the vibrator in one hand and my erect member in the other. "You are going to get fucked with these," I said. I held the vibrator up and continued: "This one is for your pussy and this one," shaking my hard meat to emphasize where I wanted it to go, "is for your ass."

"I thought I was going to get to choose."

"Well, you were busy masturbating, so I made the call."

"No."

" Why not?"

"Because that should be the grand finale. Besides, I want to try the beads first."

I put down the vibrator and took out the three packages of anal beads. They were in three sizes.

"Which set do you want to use?"

The first set of bead was the smallest and were metallic gold in color and threaded on a string.

The second was of clear violet, and the beads were not separate like on a string but one solid piece of jelled rubber, a series of orbs connected by a thinner strand of rubber. The "beads" on this one were sized from small to bigger with the largest one closest to the loop handle.

All of the beads on the third set were large, and this set vibrated as well.

We both opened the packages and inspected the beads more closely.

"Well? Which ones?" I said, displaying all three over the back of my hand like a jeweler would display a necklace to a customer.

Madison was quiet for a moment, carefully considering her choices.

"These for me." She had indicated the large jellied rubber string. "And those for you," she added.

"For me?" I answered with horror.

"Yes, Lawrence, you will love them."

"No... no thanks ... I don't want..."

"You do."

"I'm not ready to."

"You are, but you won't admit it."

"I ain't gay, and I don't like anything gay."

Madison giggled at me. "It isn't gay, Lawrence. It's physiological, and men who are brave enough to admit it are okay with it and enjoy it."

"Good for them, then," I said, attempting to dismiss the whole thing.

"Well, Mister Macho, you loved my tongue and finger, didn't you?"

It was true. I had to admit it to myself, I loved it.

Madison slipped behind me and hugged me from behind. I felt the soft skin of her tits squash up against my back. Her hand slid down and gripped my erect shlong. Madison whispered in my ear, her hot breath sending shivers throughout me. "You can't lie to me, Lawrence. I know things about you. I know your desires." She kissed and nibbled my neck.

My pilomotor reflex kicked in, and I was powerless against her.

Madison kissed my shoulder blade. She alternated kissing, licking, nibbling, and soft caresses. She kissed and licked down my back . I knew where she was heading, and I didn't want to stop her. My hair was standing on end; I was super stimulated; I felt that I could come without her even touching my penis.

She caressed me, moving her hands down to my buttocks. Then she positioned her hands on each lobe of my flanks to spread me apart. I was in ecstasy, crippled with sensation and anticipation. Was she really going to do this? Madison kissed and licked her way down, but when she got to the tail of my spine she stopped.

"So, tell me. Shall I continue? " Madison intoned bewitchingly. After a short pause when I didn't answer, she added, "Or is this too 'gay' for you?" She was both proving a point and flaunting her power over me, both at the same time.

"Lawrence, I asked you a question, two of them actually," she persisted in full enjoyment of the leverage she was wielding.

"Uh, what?" I said, not wanting to say anything. I was surrendering involuntarily not only to Madison but also to the truth that she was proving.

"Would you like me to continue?" she teased. "It's not a hard question, Lawrence."

I was still dumbfounded and didn't want to answer and prove her right. I just said, "Wuh." Giving in and answering her would be letting her win. What's more, I'd have to face the reality of my own desires.

"Come on, Lawrence. You know where this is headed, and you know you want it. You're just being defiant and difficult."

"Want what?

"Want me to lick and tongue your asshole, Lawrence." Madison said it bluntly and verbally painted me into a corner, her shameless addressing of the situation forced me to answer.

"Uh, I guess," was all I said.

"Say it!" Madison implored. "Say you want me to lick and finger your ass!"

I wanted it so bad! "Oh, please! Do it!" I surrendered.

"Not good enough, Lawrence. Say, 'please lick and eat out my ass because I love it.' Say it!" Madison ordered.

"Please lick and eat out my ass because I love it." I begged with prick-hardening humiliation, for Madison had broken me. Growing more and more infatuated with being dominated by her, I submitted.

I guess I'm what I found out was called a "switch;" a person who enjoys being dominant sometimes and submissive at other times.

She brushed her cheek against my buttock. This subtle touch sent even more chills through me, for I knew she was in the area. In my mind's eye I could see her beautiful body kneeling on the floor with her face submerged in my backside.

Madison kissed my butt cheek and then softly bit it.

"Now, tell me you love it when I lick and play with your asshole, because it brings you pleasure," she demanded, and then kissed my other buttock.

"I love when you lick and play with my asshole, because it brings me pleasure," I answered, still begging but now swimming in the humiliated feeling that just felt so good.

Madison was the master of the game. She was playing sexual chess, while I, her student, merely played checkers while being schooled.

She knew I loved having my anus licked and sucked. She knew by sticking her finger inside it, that the penetration would send me to the stars. She was well versed in her skills and understood male physiology, the secret of anal and prostate manipulation that made men blush, a feeling, a pleasure that they railed against in spite of the wonderful feeling and orgasmic enhancement it provided.

Men thought (like I thought) that it meant you were less of a man and were probably gay. Madison used this knowledge to take power over me. She knew I felt strange and scared about it but, and still, she had me begging.

She exploited it; used it to gain power over me, to dominate me, as if to say, "I have something on you, something you won't even admit to yourself, yet you can't resist it or me. I have the upper hand. I am your Mistress."

"She was becoming my dominatrix. This was why she was willing to give analingus. It permitted her to be the dominant, and she loved the slutty and dirty way it made her fell. For Madison, performing this act really helped get her off.

To not do something that felt good was blasphemy and in opposition to her carnal, sexually zen-like religion. It was foolish to her that we macho guys with our narrow-minded male egos would fight against what nature and our own bodies told us felt good. For how and why would somebody fight pleasure?

Her wet tongue lapped the back of my ball bag, the tip of her elegant nose slid up my ass crack like a castor in a slot. I felt the point of her nose poke my rectum; the touch of it on the soft knot of muscle and flesh made my entire body lurch forward, an intolerably good sensation. I felt a wonderful tickle from the two currents of warm exhalation that emanated from her nostrils. This wonderful feeling was followed by her inhaling and breathing as she dragged her tongue upward, past my taint. I felt the dampness from a trail of saliva that her tongue left in its wake as she made her way to my sphincter, which was trembling with anticipation.

When Madison finally took swirling circular laps around my asshole I almost shot my load right there.

The licking and lapping turned more aggressive. Madison began to take deeper, more intrusive jabs with her elastic tongue. As I relaxed, she went deeper and deeper, and I got looser and looser. Actually doing this felt so good in reality, along with the taboo of the idea of it: That this gorgeous woman who was rich and powerful was willing to bury her beautiful face in my naughtiest of places.

Madison performed analingus on me for a generous amount of time. It was amazing . I felt as if a gigantic wad of hot sperm would explode at any second from my full testicles, but it didn't happened.

It would have, however, had there been any contact with my swollen and ass-hungry penis.

I suddenly felt pressure against my anus. It was hard and smooth and felt larger than the surface area of my rectal opening. The pressure increased as I felt my anus being forced open, the slight feeling of dull pain evolved in to a pleasurable sensation, not that it turned from pain to pleasure, exactly, but that the pain felt good. The bead felt huge, and when Madison pushed it past its widest point, it slid into my ass the rest of the way. It was like a reverse orgasm. Instead of something exploding out of me, this was something imploding as it was pushed in. And when the first bead popped in, it sent chills from my sphincter and out to my lower spine. The squeezed nerve endings in my ass told my brain that it was cold, as if someone funneled snow into to me. Then it tingled. I let out an involuntary sigh of gratification.

"You're loving that, aren't you?" Madison playfully gloated.

I didn't answer. I couldn't answer, overwhelmed with not only the sensations but the overall erotic events that were unfolding.

SMACK! Madison slapped my ass hard for not answering.

"You like spanking my ass every chance you get. Well, now I'm running the show, and I get to spank your ass pink," she teased. "Now, answer when your mistress speaks to you, or I will continue to punish you and make you beg for the next bead! Now, tell me you love your butt beads and want more."

Mustering my faculties, I was able to offer, "I, I, oh, uh, I love how it feels when you put them in."

SMACK! She let her hand free on me again. My endorphins released, and the smacks felt like their jarring nature would extract an orgasm from me with their sharp, crisp sensory assault.

"You mean, "I love how it feels when you put them in, MISTRESS!" she corrected. "You have been naughty and need to beg me for more anal beads."

"Oh, please, Mistress! Please, may I have another bead up my ass? Please?" I surrendered, totally immersed in and loving this game.

"Well, there are eleven more beads to go," Madison whispered, and without another word forced another bead past the muscled gate of my anus.

Another jolt of pleasure took over my body. This continued 'til all of the beads were pushed in my rectum, and just the end of the strand and the loop handle protruded.

Madison arose. "I'm going to get on my hands and knees, and then I'm going to spread myself for you. Then you will use your tongue to loosen up my rear door, and then I want the large beads, and be sure to use the new lube. And do a good job so I don't have to punish you further."

"Yes." I answered submissively.

"Yes, Mistress!" Madison again corrected me.

"Yes, Mistress. " I obeyed.

"You see, Lawrence? It isn't that difficult to ask for what you want."

Madison did as she said. She got on the bed, head down and pointed her rear up. She reached back with both hands and spread her ass crack.