Chapter 7: Erica Learns to Love Anal

From Chapter 5...

I turned to the still-naked Erica and said, “You ready to learn how to deep throat a cock?”

Erica merely nodded...

As she was still naked and in my bedroom, everything I needed was at hand.

Instructing Erica to climb back up on the bed and lie crosswise, on her back, with her head hanging over the edge of the bed, I gathered the items I needed together. I doubled the four lengths of braided silk rope, fed the ends through the loop created, and placed one each on Erica’s wrists and ankles. As I drew the rope through the loop to tighten it onto her, I ensured my fingers were between it and Erica’s skin.

Silk rope is wonderfully soft, so it is fantastic for bondage, but it does get very hot as it slides across your skin.

Taking the ends, I securely fastened each of her wrists and ankles to the head and footboards of my bed. Pulling them tight, I soon had her at full stretch.

Erica’s full breasts were lifted and almost fell upward toward her chin in this position.

Taking a pillow, and much to Erica’s surprise by the look on her face, I reached under her and lifted almost the entirety of her body off the mattress so I could slip a pillow under her hips. This pushed her freshly shaven pudenda lewdly forward.

Moisture was already gathering on her slit.

Pausing to stroke and tweak her nipples, I slipped the middle finger of my right hand inside Erica’s pussy. Then, pressing the fleshy part of my finger between the second and third knuckle firmly against her clitoris, I hooked the pad on that same finger up and back a bit. Quickly finding Erica’s Gspot and rubbing my finger across it, I cruelly raked my nails across both nipples simultaneously. Then, placing the thumb of my right hand on her clit, stroking that delicious nub back and forth.

With a surprised grunt, Erica popped immediately over the edge into a shuddering orgasm.

“I never cum that easily!” She told me breathlessly.

“By the time I’m finished with you, you’ll be cumming on-demand, as Anna does, my wanton little slut girl,” I informed her.

“Do you think I can? Erica asked me almost plaintively.

“I assume you were still a virgin when you married, Harry? I asked her.

“Yes,” she said embarrassedly.

“And he hasn’t been much good at taking care of your needs? In fact, from what you said earlier, he doesn’t seem to like sex at all?

Erica shook her head sadly. “Until today, when he said what he did to you before heading out with Mistress Vicky (MsV) and Anna, I wasn’t sure he even loved me. I’ve led a very sheltered life, and Harry was the first man my mother would accept to show any genuine interest in me.

So I kind of married him because there wasn’t any other way out. Oh, he’s kind to me, not something I’m used to, but our relationship lacks passion. That’s why I want you all to show us how! I couldn’t stand years of a loveless and sexless marriage!”

“Harry is extremely emotionally and sexually repressed,” I told her. “He’s terrified he’s gay, unbelievable as that is in this day and age. So he suppresses perfectly natural desires, like wanting to crossdress, and mistakes fantasising about sucking cock and being fucked in the ass as being ‘gay’.”

“Well, straight guys don’t fantasise about or do those things, do they?” Erica asked me.

“My girl, the only difference between a ‘straight guy’ and a bisexual guy is a six-pack of beer, a hot tub, and a reasonably attractive transgirl! Trust me on this one! I’ve seen it happen way too often. Twenty minutes and four beers later, the straight guy has usually not only had his cock sucked by the Tgirl but is happily sucking hers!

I’ll introduce you to my friend Elise one day, and you’ll see what I mean. I swear she’s been fucked by first-time ‘straight’ guys more than anyone else!” I explained to her.

“The figures say about 70% of crossdressers consider themselves straight. Another large percentage consider themselves ‘transbian’, only willing to have sex with women and other transgirls or crossdressers,” I pointed out. “Harry would never go out on his own to find a cock, or pussy, for that matter, to play with. But he will do so willingly and enthusiastically if a dominant female ‘gives him permission’. MsV and Anna will certainly have had him sucking some cock by now!” I told her. I knew of their plan to take Harry to Club X.

“Harry has a need to serve dominant people. Doing that allows him to escape from his religious and social conditioning and freely express his desires and sexuality.

But all of this doesn’t matter! It just means we three, MsV, Anna, and I, don’t have to undo any bad behaviours you may have otherwise learnt. As far as your sexuality is concerned, you both are a blank page or, more accurately, perhaps, an unwritten book. I, and the other two, will delight in filling those book pages up!”

Erica nodded thoughtfully.

After this rather strange conversation with Erica being tied helplessly and wantonly over my bed, I asked her if she was ready to proceed. Erica nodded a yes to me. So, out of the top drawer, I took a product specially purchased from Honey Birdette called ‘On’, a clitoris stimulant of surprising effectiveness. Then I put a drop on the tip of my finger (all you need is a drop) and smeared it on Erica’s clitoris. The sudden warmth of this gel on her clit caused a shocked grunt to explode out of Erica’s mouth, quickly followed by an upthrusting of her hips.

“Oh, My God! What is that?” She asked.

I showed her the bottle.

“I just came, uh ... uh ... I’m coming again!”

As I said, ‘surprising effectiveness’!

Whilst Erica was distracted by the small orgasms rushing through her, I took an ‘O’ ring out of the same drawer. This ring was designed to be attached around the forehead and the back of the neck. Plus, it had straps with nipple clamps attached to the neck restraint. One of the times Erica’s mouth flew open to expel a grunt as she came, I expertly slipped the ‘O’ ring into place and tied it securely behind her head and neck.

Taking one of the rubber-padded clamps in my left hand, I first stroked, then pinched one of Erica’s nipples with my right and affixed a clamp to it, repeating the process with her other nipple. I quickly adjusted the straps so Erica could allow her head to fall almost all the way back without any tugging but giving an insistent pull on both nipples when her head was at full tilt.

I took a remote-controlled ‘vibrating egg’, a small butt plug, a cordless deep tissue massager, and some lubricating gel out of the same drawer.

The ‘egg’ slipped into Erica’s thrusting cunt without any resistance, given how hot and excited she was. Turning the vibrations up to full meant Erica began to have mini orgasms every few seconds. I could see she was heading toward a major explosion as the intensity of the egg sent her rocketing skyward towards ultimate bliss.

Smearing some of the lubricating gel onto my index finger and spreading it liberally on and around her rosebud, I slowly rimmed Erica’s anus with my forefinger. Circling back and forth slowly, I began to narrow down onto the entrance to her backdoor love canal. Applying more and more pressure on her rosebud, I was able to, eventually, slip the tip of my finger into her ass.

As my finger slowly slipped further into her ass, Erica groaned, and both bore down on my finger and clenched down on it with her sphincter muscle. Then suddenly, with a shuddering moan, Erica came again.

Her ass released its grip on my finger, and I could slide it down to the last knuckle inside her. I began to rotate my finger inside her slowly. Sliding it out long enough to add more lube, I gently stretched her ring out.

Erica was still moaning and coming from the combined stimulation of the ‘egg’ and gel. I could sense that she was coming very close to an earth-shaking crescendo. So, being gentle but working as quickly as I dared, I added a second digit into Erica’s tight warm back passage.

A deeper and even more intense groan issued from her as I managed to insert both fingers fully.

Taking my fingers out, I introduced the smallest of my various butt plugs into her anal passage. Then, with a bit of a moaned protest as the broadest part passed through her knot, I successfully inserted the whole thing into her ass.

Grabbing the deep tissue massager, I turned the vibrations on that all the way up and held it across the plug, the entrance to Erica’s vulva, and her clit. At the same time, I took hold of one of the chains to her nipple clamps and pulled quite severely on it.

With a low, high-pitched scream, Erica exploded under my ministrations. Then, uttering the first swear words I had heard coming from her pretty mouth, she screamed, “Fuck! I’m cumming! I’m cumming! I’m fucking cumming! Fuck me, you cunt. I’m cumming!”

Erica pulled so hard on her restraints that she almost lifted herself off the bed. Tossing her head back, which pulled quite harshly on her nipple clamps, she popped once, twice, and, with a much deeper and more guttural scream, a third time.

Sagging back onto the mattress, Erica opened her eyes, lifted her head, and looked at me. Then with a grateful smile, she seemed to almost pass out, letting her head loll back.

I gently lifted her head, undid the nipple clamps, and removed the egg from her pussy. A small moan emanated from her lips as the blood rushed back into her pinched nipples. Knowing this was quite an intense sensation, I gently stroked my fingers across one whilst sucking and tonguing the other before swapping around.

Erica moaned softly, so releasing the restraints I had so carefully wrapped around my lust and libido, I unzipped my trousers and let my nicely sized 7-in cock slip out from my trouser fly.

Holding Erica by the back of her head, I lowered the head of my dick until it grazed her lips. Erica’s eyes had been closed as she revelled in the sensation of being totally satiated. But they flew open as I slowly slipped my now turgid dick through the ring and into her mouth.

Remembering her lessons from last night, and swallowing quickly as the head of my cock reached her gag reflex, Erica soon accepted my entire length down her throat.

“Good girl,” I told her.

Cumming in her mouth wasn’t the plan, though. I was going to take her anal virginity this morning, so I leant forward and inserted my middle finger deep into Erica’s cunt.

Cupping my fingers down (at this angle) and back, I found that rough area behind Erica’s clit that indicates her Gspot. Pulling my hand back until my finger was almost all the way out, I drove my hand downward, forcing my middle finger to slide across her Gspot and slapping her clit and vulva as I did it.

Another surprised grunt escaped around my dick.

Using my thighs to hold myself upright against the side of the bed, I took the hand supporting Erica’s head away. This forced her to use her neck muscles to support her head so my cock could continue to slide in and out of her throat. Next, I began pulling and pushing on the plug in Erica’s butt, slowly stretching her anal love canal.

Holding the base, I circled the item around Erica’s ass to gently increase her ring size. Once I was satisfied it was stretched enough, I slid backward out of Erica’s mouth and undid the ties holding her to the bed. Then, with another surprised “Oh” from Erica, I bodily lifted her and flipped her over before retying her face down with the pillow back under her hips.

I covered her with my body and bit down firmly on the fleshy part of her body where her shoulder met her neck. Then, positioning the head of my cock at her rosebud, I whispered in her ear, “I’m going to fuck you in the ass now. Your sphincter will probably try and lockdown to refuse my dick entrance. When this happens, take a few deep breaths and try to relax. Push back as if you’re trying to expel it, then relax your sphincter. It will only hurt for a moment before it starts to feel wonderful!”

“It will hurt?” Erica asked me fearfully.

“A little at first,” I told her honestly. “I think you’ll love it shortly after that, though!”

To my surprise, Erica turned out to be quite the anal slut. There was only a momentary blockage as my cock’s head passed through her outer sphincter before, with a moaned gasp from Erica, my cock popped through her knot and slid deep into her ass.

With my pelvis pressed firmly against her plump ass cheeks, I kissed and gently tongued behind Erica’s ears and the nape of her neck, giving her time to get used to having her rear fuck hole filled.

With a shuddering sigh, Erica tilted her head back, hitting my forehead gently with the back of her head.

“Oh! Please fuck me, Sir!” She moaned breathlessly.

Moving gently at first, I began to slip a little of the length of my dick back out of her ass before smoothly but firmly pushing it back into its full depth. Erica’s head fell forward, and a deep guttural groan escaped between her lips.

“It feels so dirty and sexy. I feel like a total slut, and it feels so good! Fuck me, fuck me hard, please, Sir! I need to cum from being fucked in the ass!”

Knowing how easy it is to go too hard too soon, I ignored her repeated requests to ‘fuck me harder’ and slowly lengthened my strokes into and out of her ‘dirt hole’.

Once I was satisfied her rear love canal was fully acclimated to having my throbbing meat sliding deeply into and out of it, I removed my dick. This elicited a moaned “No!” of protest from Erica. Then, I added more lube to ensure I continued to slide in her back passage. Finally, I placed my hands on her shoulder blades, lined my turgid shaft up with her rosebud and buried myself full length into her ass with a forceful downward plunge.

My hips and pelvis hit her jelly ass with a solid meaty thwack.

Erica’s head flew back, “Fuck yes!” She swore at me. “Fuck me like the slut I am!”

Holding my weight on my hands that were still resting on her shoulder blades, I opened my legs so my thighs were outside Erica’s. Then I tucked my feet behind her shins to use my legs as leverage and began pounding into Erica’s backdoor fuck hole.

Withdrawing all but the head of my 7-in dick out of her ass, I pulled back with my legs and drove my hips forward as hard as possible, slapping meatily against her ass cheeks with every thrust.

Erica’s moans quickly turned into grunts. These grunts degenerated into virtually incomprehensible gibberish as she begged me to fuck her.

Faster, harder,” Erica demanded. “I’m a slut to be used for your pleasure.”

Sensing Erica was really close to a sensational climax, I grabbed a handful of her blonde locks at the nape of her neck, then hauled her head back and up, forcing her to arch back and lift her breasts off the mattress. Then, biting the back of her right ear whilst dragging my nails cruelly across her nipples, I thrust deeply into her warm, tight rear fuck hole once, twice, three more times. Feeling me do this, Erica exploded into a massive shaking and trembling orgasm.

A high-pitched, almost scream emanated from Erica as I raked my fingers across her nipples again. This caused me to wonder if I might get a visit from the cops. Then thunderingly orgasming, Erica came a second time.

Feeling this, I released the restraints I had wrapped so tightly around my orgasm and with a series of low grunts, I shot my seed deep inside Erica’s bowel. I must’ve shot quite a load by the amount of cum that leaked back out of her ass as I removed my softening tool from her dirt passage.