Fishing Trip

Amy clearly had a lot of experience going down on women. Her tongue felt amazing. I tried to work out what she was doing to me, so that I could imitate her. But the waves of pleasure she was sending through me demanded I give into them and I just lay back and let the feelings wash over me.

I pushed her head into my crotch and wrapped my legs around her head, anything to get more of her urgent, active, probing tongue. Quiet ecstasy wasn't so much my style and I panted and moaned and issued expletives, culminating in a guttural roar as Amy expertly pushed me over the edge.

—
I held Amy's face against my pussy as the tide of my orgasm ebbed. She didn't seem to mind, lapping at my soaked vagina, enjoying my juices. I eventually was in a state to speak again. "Fuck Amy. Never mind the Hitachi, your tongue seems motorized. What on Earth were you doing to me? Not that I am complaining. Wow, just wow!"

"Why thank you Emily. I'm glad to be able to show someone as experienced as you a new trick."

She smiled broadly. “So, are you ready for your internal exam Miss Miller?"

This was fun. "I'm ready Dr. Stevens."

"So how do we do this Em? More oil I assume. Perhaps I should get a couple of towels."

"Good idea, I'll warm up while you get them."

With Amy gone, I opened my legs wide, licked two fingers, and rubbed the saliva on to my asshole. I did the same again. I slipped first one and then another digit inside my ass. That felt nice and I tingled with anticipation at the thought of three more fingers penetrating me. I tried to contain my excitement and to focus on relaxing my anal ring.

Amy returned with two towels and another bottle of Tattinger. “My Dad has a wine cooler full of them."

I lifted my ass up and Amy arranged the towel under me. She opened the bottle and poured us two drinks. “Here's to first times, Em."

"First times."

We both drank up. I was feeling pretty woozy by now. Maybe no bad thing with what I was contemplating next.

"So Amy, we'll go slow. Neither of us have done this before. You should be able to get two fingers in me fine. We'll just go from there."

Amy drizzled oil over her first two fingers and sure enough they slipped right in. I tried to be encouraging. "OK. That feels good, now twist them about. Nice for me and good for stretching. Mmm.. I like that."

I rearrange myself slightly, getting more comfortable. “Now see if you can put a third in me. Take them out and lube all three."

Amy's three fingers stretched me. I gasped as they entered, but it was nothing I hadn't handled before. I was used to David's thick cock being buried balls-deep in my tight ass. I told her to twist and turn them to loosen me further. I liked the sensation too.

“Now Amy, let's go for broke. Push all your fingers together. Make them into a point, like you were making a shadow puppet with them. That's good."

The intensity increased. “Now more lube on me and more on your hand. We probably won't get too far on this go, so you can oil your fingers rather than your whole hand."

I settled back in the leather couch and pulled my bent legs wide apart with my hands. “Let's try. I'm going to bear down like I told you to do. So don't worry if you feel like I am pushing you out, just keep up the pressure."

I added some further advice. “You might want to twist a bit and to rock your hand back and forth. But I must admit at this point I'm relying on videos, which may not be 100% accurate."

I inhaled and exhaled. “I'm ready Amy."

The tips of Amy's three biggest fingers and thumb parted my anal ring easily enough and her little finger slipped in just after them. I breathed deeply, knowing much more was to come.

"OK. Push and twist and rock."

The tightness increased quickly and I felt a twinge of pain as Amy pushed into me. “Ease off a second."

Amy pulled back a little. I wiped the tips of my fingers in the olive oil dripping down my skin and used it to rub my clit. “Again, Amy. Ngrgh... Oh that's tight. Hold it just there."

I panted and rubbed my clit harder.

“OK. Try again... Argh!"

It was too much too soon. "Out, out please. Oh... oh... oh..."

Amy looked concerned. I was used to this and reassured her. "Don't worry angel. I just need a breather."

Peering down I had good news to impart. “Look my asshole is gaping a little."

A dark opening about half an inch in diameter had appeared, my ring of muscles clenching, but not closing it. "Let me tip further back and then pour some oil into me. You can work it in with two fingers. Oh I like you waggling them inside me."

I tried to sound confident. "Right, let's try again. This was never going to be easy."

This was going to be hard. “Lube your fingers more. Let's be optimistic and have you pour oil on your hand as well. Rub it round evenly. Great."

I nodded at Amy. “OK push your hand in as far as you did before and maybe try to open your fingers a bit. You won't feel much give at first, but try it a few times."

Amy did as I suggested. I winced each time she tried to force her fingers apart, but kept trying to squeeze her fingers out. I could feel my ring softening and stretching a little.

"Now push. Push hard. I'll tell you if I can't take it." I closed my eyes and pushed.

"Oh fuck, oh fuck, oh fuck... Annngh.. ah! oh! oh!"

I needed a break, and a progress report. "How far in Amy?"

Amy’s excitement seemed to be winning out over her initial concern. “The third joint, almost to my knuckles. Is that good?"

"Good yes, good."

I panted hard. “OK a big push and we could be there."

Amy tried again, a look of determination on her face. I thought about muscles relaxing and my body opening. I tried to yield to Amy's pressure, while still bearing down myself. I felt hot tears roll down my face. "No stop! No, no, no. I can't."

This was frustrating. “Let me have a breather."

Amy withdrew. I could see she was worried about me, but could I also detect a flicker of something else? Was she getting off on the taboo element, or was she enjoying pushing me to my limits? Or was it that she liked being in control of someone else's pleasure and pain. I couldn't tell, but something in her demeanor said that she wasn't hating this so much.

—
Amy poured us both a drink and for once I sipped on mine, trying to recover. “We are not far off I am sure."

I tried to convey an optimism that was rather different from my own thoughts. Maybe this was just too much. But I wasn't a quitter. What would make a difference? And then the obvious popped into my head. “Amy, can we use the Hitachi while you are fingering me? It might help."

Amy picked up the wand. "Sure Em. So you remember from before? On/off here, intensity here and leave the last button alone. OK?"

She held it out to me. "Do you want to hold it? You can regulate it then and I can use both hands."

I nodded. “Sounds like a plan."

I took the Hitachi from Amy, clicked it on and selected the lowest level of vibration. I touched the dome with my hand and felt the high-frequency throb. I put it against my cheek, it tingled my face. Then I touched the tip of a nipple. Mmm... that felt so good. I pressed harder, my whole breast felt like it was humming. I did the same on the other side. I could wait no longer, I put it on top of my still hooded clit. Immediately I took it away again. "Fuck that's intense. Do I have it on the wrong setting?"

"No that's the lowest. It's a bit different to a regular vibrator isn't it. Like a tequila shot compared to a low alcohol beer."

Amy held out a hand. “Let me."

I gave Amy the wand and lay somewhat nervously my legs splayed apart.

"It's like you told me about anal Em, if you aren't used to it, you need to go slow."

She rubbed the wand up and down the inside of each of my thighs. The vibrations penetrated deep into my leg muscles. It felt good. Then she held one foot and ran the Hitachi over the sole. That felt really good. She did the same with the other foot, I simultaneously felt myself relaxing and getting turned on. It was almost like an analgesic of some sort.

Amy went back to my thighs and then concentrated on where my legs met my crotch. The indirect vibrations were powerful enough to make me squirm.

Pausing briefly, Amy wanted to explain further. "Now, I can tell you something that Miss anal expert doesn't know. These vibrations make you relaxed and turned on, that means your anal sphincter relaxes as well, I read it in Cosmo."

Amy let that sink in then said, "shall we see?"

Leaving the humming wand adjacent to my most sensitive areas, Amy picked up the olive oil and poured a good quantity between my legs. It ran down on to my asshole. She scooped some up with her free hand, which she rubbed front and back across my anal opening, then moved up to my pussy to collect more oil and then back down again.

Once more she made her hand into a point and pushed this against my ass. The tips slipped in easily and before I knew it, her hand was inside me up to her knuckles. It felt horribly tight still, but somehow easier than before. She twisted and pushed and I felt more of her hand ease into me.

"I can only just see my knuckles Em. How are you doing?"

I mouthed "OK" silently and shut my eyes. But Amy did not make the final anal push that I was both dreading and aching for. Instead she moved the Hitachi directly over my clit and pushed down.

"Oh fuck, oh fuck, I'm arrh.. I came, fuck I have never cum so quickly. I... fuck I'm cumming again. I... no Amy I can't. I came again, fuck what is happening? Please no."

Amy moved the Hitachi sideways a few inches and, just as I got my breath back, she took it away again by stretching out all of the fingers on the hand that was now buried wrist deep in my rectum.

"Fuck, fuck, fuck. Oh Amy that feels so good."

"I pushed when you were busy with your multiple orgasms and it slipped right in. You really are a nasty anal bitch Em."

She waggled her fingers again at the end of the sentence and I writhed.

Amy had really got the taste for this "Let's see how much my nasty anal bitch can take, shall we? As my hand is rather occupied, would you mind setting the intensity to level 2 Em?" She gave me the wand.

"Level 2? I couldn't take level 1."

Any slapped my pussy hard with the palm of her hand.

"Ow! What the fuck?"

She did it again, slightly harder.

"Ouch!"

"Nasty little anal bitches need to do what their mistresses tell them to do."

She slapped my pussy again. I took the hint and the submissive side that David had brought out in me began to surface. Amy's whole hand was deep in my ass and the outside of my pussy stung and was turning red from the three slaps. But I could feel the inside of my pussy getting wetter and wetter and my heart beat increasing. If there was one thing I was entirely confident about, it was being an obedient sub.

"Of course mistress. Whatever mistress desires. Is level 2 sufficient, or would mistress prefer level 3?"

Amy smiled a crooked smile, one that said "game on" to me. “Level 2 will suffice for now, but no more disobedience from you, or there will be consequences, do you understand?"

"Yes mistress. I have set the level at 2 as you requested. But I was a little slow in doing so, please don't punish me."

Amy slapped my pussy again, this time waggling her fingers in my ass. I screamed.

"No screaming or it will go worse for you."

"Yes mistress, thank you mistress."

I been to feel lost, not an unfamiliar feeling. "May I please stroke my pussy, it is so sore?"

Amy was magnanimous. "Permission granted."

I gingerly felt my pussy. It was inflamed and tingly numb, it felt hot. “Thank you for showing me the error of my ways mistress."

"That's much better. Now let's return to our experiment."

Amy lowered the Hitachi on to my clit again. If it felt like fireworks before, it was more like a grenade going off now. Despite the cacophony of feelings in my clitoris and pussy, I just about felt Amy's hand being thrust further up my rectum before exploding, this time with a vertical jet of ejaculate: one that continued until Amy removed the wand. Fuck that thing makes you cum quickly.

"I didn't give you permission to squirt. I am not unpleased, but I will still need to punish you, it's a matter of principle."

Amy lay the still buzzing toy across my tummy and leaned forward between my legs. She slapped each breast twice, once from the left palm open, once from the right with the back of her hand. I heaved and my ass muscles tightened on her hand with each impact. I could see my small breasts turning as red as my pussy.

Amy grinned evilly. "You have a pleasing skin color to slap. I think you need more."

Amy slapped my breasts four times again. It stung so bad, but I pushed past the pain to find the pleasure as any good sub learns to do. “Thank you mistress. I deserved that. Permission requested to squirt again later."

"Granted. Now level 3."

I obediently turned up the wand and handed it to her.

Amy provided me with an update. "I have a couple of inches of my forearm in your ass now. Would you like more."

There was only one reply. “If mistress pleases."

I was impaled on Amy's arm, covered with my own cum juice and my pussy and breasts ached dully. I wanted more.

—
Amy put the Hitachi on my clit and everything became a blur. Half opening my eyes, I saw a fountain spouting from between my legs and Amy leaning into it mouth open, her beautiful face being splashed by my juices. That wasn't the only thing she was doing. I felt an incredible pressure in my rectum. I think I may have blacked out for a couple of seconds. When I opened my eyes again, the wand was lying across my stomach again.

Amy sounded exultant. “You may look bitch."

I raised my head and leaned forward as much as I could with an arm up my ass. Speaking of which, there was only about three inches of Amy's arm sticking out of me before the bend of her elbow. I guess I never do things by halves. As I looked, Amy twisted her fist inside me sending paroxysms of pleasure through my already over-stimulated body. I whimpered and a single tear rolled down my cheek. It felt like too much, but I also loved it. This is the lot of a submissive and I accepted it.

Amy handed me the wand. “Level 4 and elbow deep. Your mistress commands it."

"Yes mistress."

Trembling with both fear and excitement, I set the intensity on maximum and handed it back to Amy.

“Now what your mistress is going to do is force the rest of her forearm up your ass. Do you understand? A nod is OK."

I nodded.

“Good."

Amy paused. "But you only get the Hitachi if you answer my questions truthfully. Is that clear. Again nod if it is."

Once more I assented. I would have done anything she asked of me.

"OK. So I'm starting to push. Can you feel your rectum being stretched? Yes? Is it painful? Yes. Do you want the Hitachi? Yes again."

Amy’s tone became abrupt. "Well you can have it. There are three inches of my arm to go and so I'll ask three questions. Nod if you understand. Good."

Amy put the wand on my stomach and oiled up what remained of her forearm.

"Ready? That's a good little bitch."

I couldn’t believe how much Amy was enjoying her role. "First question. Who is your mistress?"

"Amy Stevens."

"Good anal bitch."

Amy picked up the wand and put it on my clit and I can't even begin to describe the sensation. All I can say is I came violently within ten seconds, spraying cum again. When Amy removed the Hitachi, my ass was even more full, even more stretched.

She seemed pleased. "Two inches to go."

"Question two. Who did you lose your virginity to?"

Even in my altered state, this gave me pause.

"Rob Marcello." I really couldn't think of a better answer. Not with my ass full of arm.

"Oh dear little bitch. Our survey says no."

Amy laughed. “Rob is gay, I thought everyone knew that."

A strange light animated Amy’s eyes. “The next inch is with no Hitachi. Unless, unless you want to reconsider."

“No it was Rob, before he was gay. Or rather it was a lapse on his part, we were both drunk and... aieeee!"

I screamed as Amy eased her arm a half inch deeper into my anal cavity.

"OK, OK, you win. It was David. I lost my virginity to David. Now give me the fucking Hitachi."

Amy spanked my pussy hard again. It was already so sore and this really hurt. I wailed as tears streamed down my face.

"I'm sorry mistress. I don't know what came over me to speak to you like that. Please mistress can I have the Hitachi, if it amuses you to give it to me?"

Fuck my pussy stung, but beyond the slap, Amy seemed to have no reaction to my semi-revealed secret. To be honest, I was such a pent up ball of emotions and sensations that I really didn't care much anymore. I had cum so much and so hard and was so stimulated by both the anal fisting and punishments that I hardly knew which way was up. Whatever Amy was thinking, she seemed to have a plan and was sticking to it. Before she applied the magic wand, she put her face close to my pussy and opened her mouth wide. “Squirt for your mistress anal bitch, I'm feeling thirsty."

Amy lowered the Hitachi. This time I was better able to tell what was happening to me. Nothing before had prepared me for level 4, but this second dose was slightly more tolerable. Having said that, level 4 was still the sexual equivalent of a thermonuclear explosion.

Again I came close to instantly, spraying gouts of juice that Amy did her best to swallow, but it soaked her hair and ran down her face as well. At the same time, I felt Amy push her arm deeper. I was beyond telling what was making me cum, the extreme anal probing, the wand or - most likely - both.

"One inch left bitch."

A note of softness entered Amy’s voice. "Do you want me to stop?"

I shook my sweat-covered and tear-stained face. I wanted the next inch badly and I wanted to cum again.

"OK. Question three. What is it with you and Mr. Skowronski?"

All my defenses were down, Amy had clearly probed my mind as deeply as she had probed my ass. She had obviously made connections and reached conclusions. But all I wanted now was to be anally fisted elbow deep and to have the Hitachi pressed against my clit.

"He's my Father's best friend. We called him Uncle Dave when we were growing up. I lost my virginity to my Dad's school friend. He's still my fuck-buddy and I don't care if you are sickened by me, just give me the fucking wand and ram your arm all the way into my ass!"

Again the softness. “I knew Emily, it's OK."

Amy leaned forward and kissed me very tenderly. Then she slapped my face. "That's twice you have told you mistress what to do bitch. We can't have that."

Before I had recovered from the stinging blow, she lowered the Hitachi on to me and pushed it down hard.

"Last inch bitch."

I screamed and screamed and screamed. My legs and arms thrashed wildly. My back arched as if it would break. And, as Amy pushed her entire forearm into my body, and twisted it left and right repeatedly, I came and came and came.

I have no idea if it was one long orgasm, or many separate ones with tiny pauses in between. All I knew was my ass was spasming, my clit was suffering extreme torture of the sweetest kind and my pussy had turned into Niagara.

Later Amy told me that she had held the Hitachi on my clit for two minutes. At the time it felt like an eternity. I couldn't remember a time when I was not constantly cumming and squeezing my anal muscles on ten inches of hand and arm. And gushing, gushing, gushing. Satiating my mistress's thirst.

—
PART III - TO THINE OWN SELF BE TRUE
I had questions. “So how did you know?"

"That you were a sub? A domme develops a feeling for that sort of thing."