My Best Friend Emily Ch. 05

"I see," I said, pulling my jeans off of my legs. I stroked my chin thoughtfully and moved closer to Emily. The dildo was still buried in her pussy. Her face was soaked, and there was a puddle on the desk around her. Lisa must have really squirted on her. "Did you use the butt plug?" I asked.

"Yes sir," Lisa said. "I think... I think... she's a dyke... and she liked it."

"Well, in that case we definitely need to try something different," I said. "Come here girl," I said to Emily. She started to push herself up on the desk, and then she reached in between her legs to pull out the dildo.

"No!" I said. "Bad girl! That stays in," I added, "Hold it inside with your hand if you need to." Emily managed to slide off of the desk, holding the dildo inside of her. She took one, two unsteady steps until she was standing in front of me. "On your knees girl," I said, and Emily obligingly sank to her knees. I grabbed the waistband of my boxers and pulled them down, my erection bouncing free. "Have you ever sucked a man's penis before?" I asked.

"No," Emily said meekly.

"Don't lie to me," I said menacingly, and I raised my hand like I was going to slap her, but I couldn't. I didn't have it in me.

"I've never been with a boy..." Emily said, sounding as much like an innocent schoolgirl as she could manage, "Or a man," she added, biting her lip and staring at my erection.

I felt my cock twitch. She was a great actress, after all. "Well, you're about to learn a very valuable lesson," I said. "Come here and put your hand on the shaft," I said, and Emily quickly moved closer and placed her hand around my shaft. "Now, stroke it back and forth," I said, "Slowly," I added, as Emily started jerking her hand clumsily back and forth. She was really pretending she didn't know what she was doing, I thought.

I let her stroke me for a bit. "Okay, now put your mouth around the head," I said. Emily stuck the head of my cock in her mouth. "Like this?" She asked.

"Don't talk with your mouth full," I said sternly. Emily was staring up at me, her mouth around my cock. "Now, wrap your lips around it," I said, "Like you're sucking on a straw," I added. I felt Emily's lips close around my cock. "Now, move your head back and forth." Emily started moving, but from side to side. "No! Stupid girl," I said, and I took hold of her head in my hands, wincing at the memory of what I had done to Lisa just the night before. I glanced at Lisa, who was watching us with a sort of detached interest. I took a deep breath and tried to recover my character. "Move your head back and forth along the shaft, like this," I said, and moved her head back and forth with my hands. Once she pretended to get the hang of it I pulled my hands away. I let her suck at my cock for a while, enjoying the sensations. "You can use your tongue too," I said, "Use it to lick the head."

Emily slid her mouth off of my cock with a wet plop. She took hold of me with one hand. "Like this?" She asked, and ran her tongue along the underside of my cock.

"Yes, very good," I said as Emily put me back in her mouth. She was becoming less the schoolgirl and more the experienced Emily that I knew. I started to think about what should happen next. Should I just let Emily blow me until I came? I made eye contact with Lisa. Who was in charge of this role-playing fantasy now?

I heard a plopping sound and a thud somewhere below me. It took me a few seconds to realize that the dildo had fallen out of Emily's pussy. Lisa had a better view from her vantage point. "Headmaster," she said, "The slut let go of the dildo."

"Really?" I asked, and I struggled to come up with a new idea. "You need to be punished for that, my dear." I said that to buy time while I thought.

"You need to fuck her in the ass!" Lisa shouted, and I stared at her, shocked. "That's the punishment for losing your dildo," Lisa added.

Anal sex was something I had never done before. It wasn't high on my list of things to try and Lisa certainly never asked for it. I looked down at Emily. She was holding my cock in her hand, staring at me fearfully. I couldn't tell if she wanted me to do it or not. I didn't know enough about her sexual past to know if she had ever done it before. I started to stammer. "Umm... yes... well... that is the punishment."

"Yes!" Lisa said. She could barely contain her excitement. Why did she want this to happen so much? "On all fours slut," Lisa said, and Emily let go of my cock and turned to the side, raising her backside in the air.

Lisa moved up beside me. She moved right up to my ear and whispered, "She has a safe word. Yadier, whatever that means." I smiled and nodded. I knew what a safe word was, although I had never been in a situation where one was needed before. Lisa knelt down beside Emily. "First, this goes back in," Lisa said, taking the dildo off the floor and inserting it back into Emily's pussy. I heard Emily gasp as the huge rubber dildo was pushed back into her pussy. "Next, this comes out," Lisa said, and pulled the butt plug out of Emily's ass. Emily groaned as the much smaller object was pulled from her ass. My cock was absolutely enormous by comparison. I started to get cold feet. Was this really such a good idea? I know that just this morning I was furious at Emily for insinuating that maybe we should have been together all along, and I fucked her out of anger, but even then I had no intention of actually hurting her. Would this hurt? I struggled to not break character and ask. She is okay with this, I said to myself. She would use the safe word if she wasn't.

Lisa had gone to get the bottle of lube, and now she was spreading it liberally around Emily's asshole. I looked at Emily. Fifteen years of friendship had given us a bit of a telepathic link. Just tell me whether or not you really want this, I thought at her. Emily smiled subtly and winked at me. Yes, she wanted me to do this.

Lisa moved away and I took a deep breath. I moved behind Emily and stared down at her butt, which was still red from the spanking. I took her butt cheeks in my hand and spread them apart, revealing her anus. I took my erection in my hand and slowly pressed it against her anus. I imagined that it would be like entering a really tight pussy. I felt the tip of my cock start to push through the opening. Emily grunted, and I fought to stay in character. "Just relax, young lady," I said, and I had to suppress a chuckle. Emily and I were the same age too. In fact, she was younger by exactly eight days. I remembered hearing about women needing to relax their sphincter muscles in order to enjoy anal sex. I heard Emily let out a deep breath, and I could feel her relax. Her opening grew a little bit, and I was able to slide a little further inside.

"Oh my God," I heard Emily mumble, "You're so big." Lisa was suddenly beside me again with the bottle of lube, pouring more onto Emily's ass and my dick. I slid myself in another inch until Emily grunted again. I fought the urge to ask if she was okay. She would use the safe word if she wanted me to stop, I thought. I scooted forward a little bit on my knees and pushed myself further into her. She grunted again.

"You should start moving back and forth now," Lisa said, "Headmaster," she added belatedly.

Part of me wanted to ask how Lisa knew about how to have anal sex, but I was grateful for any kind of direction. I slowly pulled myself back and then pushed into her again. I heard Emily suck in a breath of air. This time I couldn't hold back. "Are you okay?" I asked.

"Yes," Emily said, "Just go slow."

I thought back to the summer after high school when I took Suzy Clements' virginity. She was so tight I could hardly push myself into her. I remembered taking my time, pushing into her bit by bit until I was all the way inside, then slowly moving in and out until she was comfortable. I ran into her a few years ago and she belatedly thanked me for being so gentle with her. I can do that now, I thought.

I eased myself back and forth, in and out, little by little, until I was able to start pushing myself in deeper. I sensed movement around me. It was Lisa. She had reached under me and taken hold of the dildo still sticking out of Emily's pussy. She started moving the dildo in and out of Emily's pussy. I heard Emily gasp and start to move her hips along with Lisa's rhythm. She was now getting fucked in both holes.

"Look at you now, you little slut," Lisa said, as she worked the dildo in and out of Emily's pussy. I was finding it easier and easier to move in and out of her, but it was still really tight. I felt my cock being squeezed, and it was more stimulating than being inside a pussy. I wasn't sure how long I could hold out.

"Being fucked by a dildo in your pussy by your teacher while the headmaster fucks you in the ass," Lisa continued, "You're a dirty little dyke slut. Say you're a dirty little dyke slut."

"I'm a dirty little dyke slut," Emily mumbled.

Lisa slapped Emily's ass, barely missing me. "I can't hear you!" She shouted.

"I'm a dirty little dyke slut!" Emily screamed.

"And you like it, don't you?" Lisa asked.

"Yes! Yes!" Emily cried. "I like it! Oh, please, fuck me!"

Lisa slapped her on the ass again. "No swearing!" She shouted. I laughed.

Emily moaned. "Do me," she said tentatively. "Do me! Do me really hard! Oh, it feels so good. I feel so full... I feel like I'm going to burst! I'm going to cum! Yes! I'm going to cum! Fuh... do me harder! Yes! Oh Guh... oh man... oh man... OH!" Emily suddenly froze in place, legs shaking, as her orgasm hit her. Then she collapsed to the floor, pulling away from me as she did. Emily rolled onto her back. The dildo was still inside of her, and Lisa reached around me and pulled the dildo free. A rush of liquid squirted from Emily's pussy, and her hips jerked. She grabbed at her pussy with her hand. "Wow," she mumbled.

"You squirted," Lisa said. She sounded, I don't know, impressed? "You dirty little dyke slut," she added. "And now for the next punishment," Lisa said, "Headmaster has to cum on you."

I didn't need much encouragement. I was thinking pretty much the same thing. I took myself in my hand and moved until I was hovering over Emily's prone body. It isn't going to take much to cum, I thought, starting to stroke my well-lubricated cock.

Emily was staring up at me, her chest still heaving and her hips shaking. I wasn't sure she heard anything Lisa said. "Oh my God that was amazing," she mumbled, and I wondered if she had even regained her senses.

I felt myself going over the edge. I grunted and bucked my hips as my orgasm hit, my cock shooting one, two, three spurts of cum onto Emily's belly. Emily was staring at me as I emptied myself onto her.

"And now for the final punishment," Lisa announced. "You have to eat headmaster's cum."

I turned to look at Lisa. Emily eating my cum was what caused Lisa to go berserk last night. Now she was ordering Emily to do it?

Emily had regained her senses enough to slip back into character. "But..." She started to say.

"No buts!" Lisa said, "If you want to be forgiven for losing your panties, you must do this."

Emily and I locked eyes. She reached down with her hand and scooped most of the cum off of her belly with her pointer finger. She slowly put her pointer finger into her mouth, sucking at it, trying to look like she was disgusted. Then, her face broke into a smile. "I like it, ma'am," she said.

I burst out laughing. I was surprised to see that Lisa did too. All three of us were on the floor of our home office, naked and laughing.

"Okay, break," Lisa said.

"You mean," Emily said between laughs, "We can break character now?" We all started laughing even harder.

"Oh my God," Lisa said to me when the laughter died down, "When you walked into the room I almost lost it."

"How long were you outside the door?" Emily asked.

"From when Lisa was spanking you with the ruler," I said.

"And you just watched?" Lisa asked.

"Yeah," I said. "It was a sexy show. Very sexy," I added.

"I'm glad you liked it," Emily said.

"You were quite a sport," Lisa said.

"Well, believe it or not," Emily said, "It wasn't my first submissive role, or my first anal, or my first DP..." she trailed off.

We all fell silent, Emily lost in her erotic memories, Lisa and I imagining what she had done in the past.

"I think we need to clean up," I eventually said.

"Hey, let's use the Jacuzzi," Lisa said, "We never use that thing."

"Yeah!" Emily said, and she stood up and she and Lisa were both walking towards the master bedroom before I even moved. I stood up slowly and followed them. We climbed into the Jacuzzi and staked out our spots while it was still filling with water. Lisa and I sat on one side, and Emily sat on the other. I took a moment to study Lisa. I hadn't really had a chance to talk to her since last night. She locked me out of the bedroom, and the next time I saw her she was pulling me into the muddy flower bed for a sexual adventure I never would have thought her capable of. The next time I saw her she was beating Emily with a yardstick, putting dildos and butt plugs in her, sitting on her face, and suggesting that I have anal sex with her. I was wondering yet again if I even knew who my wife really was.

Emily, for one, was eager to talk about what had just happened. "So, a lot of firsts today," Emily said, "Your first sado-masochist role-playing adventure, your first anal," she said to me, "And my first squirt."

"That was fun," Lisa said, and I nodded. "I have a lot of other ideas," Lisa added. "I spend a lot of time fantasizing..."

"Why didn't you ever tell me about it?" I snapped. I tried to sound casual about it, but I don't think I did.

"Well, for starters, most of my fantasies required a woman," Lisa snapped back, "And we didn't have one handy until just last week."

I was briefly taken aback, but I recovered, "Well, not that little romp in the mud before," I said, "Why didn't you ever say anything to me?"

"I... didn't feel comfortable," Lisa said. "That's a pretty wild fetish. I was afraid you'd think I was sick, or crazy."

"I know," I said, "But you knew that I went off and watched porn. Did it ever occur to you that maybe that was the kind of thing that I watched?"

"Really?" Lisa said. "You watch videos of women... in mud?"

"Yes," I said, "If you had told me about your interest in it years ago..." I trailed off. "Never mind. We've been over this already." I eventually said.

"Stuff like that... is on the internet?" Lisa asked.

"Everything is on the internet," Emily chimed in.

Lisa didn't reply. She seemed lost in thought. The Jacuzzi filled with water and I turned on the jets. All three of us jumped as the suddenly churning water tickled our bodies. Emily let out a deep breath and sank deeper into the water. I felt her legs brush up against mine. She caught my eye and smiled at me, a devilish smile that made me think she was up to something.

"I think it's my turn to freak out and storm out of the room," Emily said. "So, blah blah blah, blah blah blah!" She rose out of the water, waving her arms in the air like a lunatic. "All righty then!" She shouted, climbing out of the tub and grabbing a nearby towel. She calmly dried herself off, while I laughed hysterically and Lisa stared at her like she just lost her mind. Emily finished drying off and started to walk out of the bathroom. She stopped. "Oh, and another thing. Pbbbbttttt," Emily blew a raspberry at us, and then left the room. Then she came back to the doorway. "What do you think, pizza for dinner?" She asked, and turned and left again, leaving me and Lisa, naked in the Jacuzzi, staring at each other.

Whatever Lisa thought of Emily's outburst, she recovered quickly. "Maybe later," Lisa said, placing a hand on my knee, "We can go on the internet and watch some of those videos of women in mud."

"Of course," I said, leaning back in the Jacuzzi, feeling for the first time since the whole thing began that maybe things will work out just fine, after all.

I hope you enjoyed the latest installment of this series. I know it was a very diverse collection of fetishes and situations, and I hope everybody found something to enjoy and nobody was offended by any of the subject matter. As always, any feedback is greatly appreciated.