Amber the Babysitter Pt. 12

Amber the babysitter 12.

I think I fell in love with Amber five times during our relationship before we got married. Each time we crossed a boundary or threshold, had a new adventure or opened ourselves up more, the deeper I fell in love with her.

The first time I knew I was in love with her was the night we had that heated make-out session in my car after she got off of work when we agreed to continue dating each other after we masturbated in front of each other. The second was after months of dating when she decided to move in. The third was when she graduated, and I couldn't wait to have her. The fourth was our engagement night with our wedding rings. And the fifth, well, was the night she came back home after she left me for a few weeks to get herself together. That night, outside of our wedding night - which, comically enough - was not as hot and erotic as we thought it would be, was by far the best sex we had ever had. And here's why.

While making love to her that night after we fought, cried, and apologized, we both had admitted and accepted our fears. It was more emotionally moving for me than I had ever experienced before. I have no doubt it was the same for her. The more we touched, caressed, kissed, held each other, and orgasmed after weeks apart, the closer I felt to her. Even as I wrote in my previous story, when she got up to use the bathroom, seeing her walking naked in front of me turned me on beyond belief. As much as some of you may question her loyalty, since she walked out on me, I had no doubt she was home for good. From then on, we agreed to discuss our problems, concerns, and fears without shutting down or running away. And that made me so fucking wet and aroused that I left a wet spot on my sheets where my ass was sitting.

In the moments after smoking our cigarettes, Amber asked me, "Did you say you wished you could get me pregnant?"

I chuckled aloud and felt embarrassed, but I honestly answered her, "Yes."

I furthered by explaining that I felt so close and deep emotionally with her at that moment that I wished I had a dick so I could get her pregnant. Like men and women do. I explained more that I just wanted her to be happy and be the woman she needed to be, and if we could make children together somehow, I wouldn't be opposed. Now, I know I can't get her pregnant. I don't need the comments. But at that moment, I took that next step with her, and I felt that if I could give her anything, including children, I would have.

Amber leaned over and kissed me softly, the way a lover does for their other half during emotional times such as these, and whispered, "I'd get you pregnant too if I could, but I like things just the way they are. I'd rather have your pussy than a dick, but I'm not opposed to more toy time."

I think it hit us both simultaneously because not only did we have the strap-on, but we also had the new double-ended long dildo I bought that we had never used.

"You know..." she said. "We never did try that toy you bought a few weeks ago. Maybe...... we could."

I kid you not when I tell you that literally five seconds later, I was at my dresser drawer pulling it out. Not figuratively, I mean literally at my drawer, hand digging around under clothes until I had it in my hand and was removing it from the drawer.

When I turned back around, walking towards the bed, and Amber saw it in my hand, she threw the sheets off of her, spread her legs open, and whispered, "Come fuck my pussy."

My legs got weak hearing her say that. As I crawled back into bed, I handed it to her, leaned further over, opened my nightstand table, pulled out our bottle of lube, and sat on my knees next to her, taking the dildo back.

I squirted a very generous amount into the palm of my hand and started stoking one end of it, getting all lubed up. I could see Ambers's hand swirling around her clit, and I knew, just as she did, that momentarily, I was going to be ramming this soft-rubbed, flexible double, headed dildo right into her wet awaiting pussy. I had the wild idea to act like I had a dick, so once it was well oiled up, I stood up over her, with my legs on each side of her body. I slid the dildo between my legs, one dick end pointing towards her while the other side pointed out and away from my ass.

I spoke out, "You wanna suck my dick, baby," as I grabbed the back of her hair and started pulling her face to it.

Amber didn't even have a chance to get situated before the dildo passed her lips and into her mouth. I pushed it in so far while pulling her face towards it that she gagged. I backed off a bit and let her suck it like it was my own, reeling in the pleasure of watching it slide in and out of her mouth.

"Yeah, get me good and hard, baby, so I fuck your pussy." I moaned out.

I was so wet that I felt juices running down my leg. I had the thought of ramming one end into my pussy, while she was sucking the other. But tonight, I was going to fuck her so hard with it that she would be begging me to stop. When I felt she was ready, I pulled my dick from her mouth, forced her onto her back, slid between her legs, licked for the bottom of her slit, to her clit, spread her lips with my fingers, and rammed the head of the dildo deep inside of her.

I started slowly and deliberately, but during our actions, I pushed it in as deep as she could take it. I began pumping her as hard as I could. She orgasmed quickly, and just as she did, I switched hands with the dildo, found the lube, squirted a shit load on her pussy, which ran down between the crack of her ass. I rubbed my fingers over her asshole, and when it was time, I slid a finger deep into her ass.

I pumped my finger and that dildo consistently, with a long, deep motion. Soon after, one finger turned into two as she whimpered and moaned. When I felt she was ready for that dildo to be deep in her ass. I bent the flexible dildo in half, in a horseshoe shape, and fumbled around, trying to slide it into her. When I finally got it in her ass, I started pumping back and forth real slow. I was extremely thrilled and overly aroused watching both heads of the dildo slide in and out of both holes, while my hand was holding the bent end like a tool, thrusting it in and out of her. I pumped slowly and cautiously. Then I would speed up, making it hard and deep, then slow back down, letting her come down from the pressure of two dicks in her at once.

Occasionally I would put my mouth over her clit while I was pumping her, and that action would send her into overload. It was amazing seeing the dildo sliding in and out of her pussy and her ass at the same time while she whimpered, whined, and shook. I fucked her long and deep until that next orgasm exploded from her ass raised off the mattress, and she squirted everywhere.

After she came, her body went limp, her legs slid downwards, and her head tilted to the side. I knew she had come hard and needed a minute, but I needed to be pleased as well. I left the dildo inside of her, crawled across her body, and up on top of her, putting my soaking wet pussy on her lips. I forced myself down on her so hard, just like she had done to me weeks prior, that I didn't think she could breathe. She ate me hard and feverishly until I came all over her face. I was so wet that we were done; we discovered that both sides of her pillowcase, on each side of her head, were soaked with my juices.

After I came hard, screaming her name while rubbing my clit raw, we spent the next hour going back and forth, sticking the double-headed in each other's pussies, and asses. We even tried doing it simultaneously, with our legs entwined, like you see in porn movies. It was well after 4:30 A. M. before we finally stopped fucking and fell asleep in bedding and pillows that were soaking wet with pee, saliva, cum, and lube.

I awoke at 8:34 a. m., having to use the bathroom. I noticed Amber wasn't in bed with me. After I finished my business, I wandered down the hallway, thinking maybe she couldn't sleep well, and in an attempt not to disturb me, she went to sleep on the couch. Just as I reached the end of the hallway, I could hear her whimpering softly. I could see her standing at the counter by the coffee machine, naked, her legs spread apart, her body slightly bent downwards. I could tell her hand rubbing up and down over her pussy; occasionally, her fingers would be rubbing on her asshole. I stood silently watching her masturbate, getting aroused seeing her taking care of herself, even after the long night of sex we had.

I was aching in my lions, and I wanted to please her more than I already had. I turned my back and softly tip-toed my way back down the hallway to my room. I pulled the strap-on out of my drawer and started to slide it on, getting the fake dick situated and sticking out away from me. I grabbed the lube from the floor, and I hoped that by the time I got it all on and was walking back towards her, she wouldn't be finished.

As I got to the end of the hallway, I could hear her moans increasing. I couldn't see her fingers, but by the movement of her arm, I could tell she was working her clit hard. Just as I was walking up behind her, she pulled her hands from her pussy, spit on her fingers and slid her hand deep between her legs, and started rubbing around her asshole. Seconds later, her index finger slid right up in her ass and was slowly sliding in and out. I knew she had finally come to like anal, and now, even in the morning, on very little sleep, she was naked in my kitchen, fingering herself in the ass. And I couldn't have loved it more.

She must have heard me coming because she pulled her hand away abruptly and spun around to see me standing there naked, just feet behind her with the strap-on attached. I could tell she was embarrassed and taken aback that I had caught her doing what she was doing. I offered her words of comfort and love, which are hard to do after you catch someone masturbating. I know the situation was awkward, and I am positive she didn't expect me to be standing there wearing a dick. As I explained to her, I got so aroused watching her play with herself that I thought, what a good time for some more toy experimentation. After a bit of my rambling and babbling, trying to convince her it was alright that she was masturbating, I said,

"I was watching you play with yourself. I saw your finger in your ass."

"I went and got this so I can help. Do you want me to put it in your ass?" I asked.

Amber turned bright red, smiled, dipped her head, and softly spoke out, "Yes."

"Turn around then," I suggested.

Amber turned around hesitantly and fearfully, but she had trust in me. As she turned, she placed her hands on the counter, bent her body over, shifted her legs apart, and walked right up behind her. I kissed her back, wrapping my arms around her and whispering that I loved her. I felt so aroused by the position she was in and the fact that she had been masturbating that I thought I needed to do something a bit more special.

I knelt behind her and gently kissed and licked both of her ass cheeks. My hands wandered up and down over her legs, across her hips, and even onto her pussy. I slid my tongue right up and in between those sexy tight cheeks and started eating her ass out like I would eat her pussy. My tongue swirled around it, getting it slippery wet, my hands still caressing her body. I pushed her cheeks open more, pushing my tongue in as far and as deep as I could. I licked it, I swirled my tongue all over it, and I teased it with my fingertips. Her moans and groans increased quite unexpectedly. I had only eaten her ass out one other time, but today was different. Today she wanted a dick in her ass, and I was going to make it the best anal sex she ever had, starting by orally pleasing her.

When I knew she was ready, I rose from my kneeling position, popped the top on the lube, and squirted a lot on her asshole. I pushed my fingers hard onto her back entrance and rubbed all over her backside. I slid one finger in and stood over her, watching my index finger slide all the way in and out of her as she began to loosen up, whimper, and enjoy the sensation of being taken from behind.

As I pumped her ass and she started to loosen up, I slid a second finger in. This grabbed her attention more than any time before, and I think my force of pushing every inch of my fingers into her was making her feel how different and unique anal sex is.

I spit all over my hand, and with the combination of extra lube, I started jacking off the strap-on dick, getting it all slippery wet. As I continued fingering her from behind, Amber's legs shook. Her ass lifted then sank, and I could tell she was ready for that dick deep inside of her. I pulled my fingers from inside of her, edged myself in, holding the dick in my hand, and with just a drip more lube on her open asshole, I slid that dick up inside of her.

Amber lifted onto her tippy toes as I pushed the dildo in. I started slowly, but I promise you that before a minute was out, my speed and depth had increased, as did her moans and groans.

"You like that dick in your ass?" I asked.

"Yes!" She chirped out loudly as her body rocked back and forth with my every thrust.

"You wanna cum with my dick in your ass?" I grunted out.

"Yes!" She cried out.

"Then Fucking Cum!" Was my response as I was ramming that dick deep into her.

This time, there was no newness or awkward, unsure hip swings. This time, I had it down to a science. This time I had my momentum and depth dead on, and every inch of that 7-inch strap-on dick was sliding into her ass. I knew this was the first time Amber had been bent over a counter getting penetrated, and this was the first time she had been bent over with a dildo deep in her ass.

I pumped hard and fast. I wouldn't let her play with her pussy, and I wasn't going to play with it either. She was going to cum with my dick in her ass. Otherwise, she wasn't going to cum at all. Call it being abusive, or rough, or even demanding, but I was going to make her beg me to fuck her in the ass every chance we got. And I would expect her to fuck me back when I wanted it.

Minutes went by, and Amber moaned, groaned, whimpered, and whined. Just when I was about to give up, I was almost ready to call it a day and give myself a break. She started whimpering out;

"Jill, I'm going fucking cum. Don't fucking stop. I'm gonna cum."

I got so excited and aroused that I continued pumping her as hard as I could. I could hear her screams of pleasure and pain until she started mouthing out, "I'm fucking cumming. I'm fucking cumming."

Her body twitched, her legs shook, and she belted out in pleasure. I smiled deviantly knowing she had just cum with a fake dick deep in her ass.

"Holy fuck!" She cried out as I just kept sliding that dick in and out of her.

"Don't fucking stop." She demanded.

I kept pumping and pumping while her fingers started rubbing her clit, until she exploded a second orgasm minutes later. Just as she exploded, her legs gave out, and she collapsed onto the kitchen floor. I stood over her, seeing her chest rise and fall, the sweat beading off of her forehead, her legs trembling, her eyes closed, her body shaking. "Jill," she spoke out, "I fucking love you. I'm never leaving again."

"FUCK!" She screamed out in anger and acceptance. "I'm a fucking lesbian, and I love it in the ass."

We both giggled hard, but we were trying not to laugh at her words to make it embarrassing. But we snickered like girls telling secrets because of what she said. I honestly believe she was speaking the truth.

I knelt down on the floor and held her. Her body seemed so small, so fragile, and so exhausted that I felt I would have almost had to pick her up and carry her to the couch. We whispered words of love to each other as we huddled together, cold, naked, and sweaty, on my floor for quite some time.

After huddling on the floor for a while, we finally got up. I slipped the strap-on off, set it on the counter, and we made our way to the couch to cuddle under the blankets. Her legs were so shaky and unsteady as we walked towards it that I had to help her make it.

We huddled under a big, warm blanket, dozing back off rather quickly. Some hours later, after we were both up and awake again and had gotten somewhat dressed, I made us some lunch. As we sat and ate, Amber had this look in her eyes that I had never seen before. I don't know if it was unconditional love. The fact that she had her ass violated last night and, then again today. That between us, we probably had 14 orgasms from last night on, or the fact that she finally knew her place in life. But either way, the look of longing didn't last long because after I cleared the table, she took me.

Amber forced me onto the top of the dining room table. She put me on my knees, facing away from her, pulling my pajama bottoms down and off. She knelt on the chair and started eating my pussy from behind. But just as I started getting close to orgasm, she shifted her face upwards and ate my ass out like she had never done before. She continued eating me until I came hard from her tongues, deep warming pleasures. When I thought it was over and she had done what she was interested in doing, I couldn't have been more wrong.

I was told, "Don't you fucking move," As she pointed her finger at my face, pulled her clothes off, turned and walked away from me.

What I didn't know was that Amber took the strap-on off the counter, washed it, slid it on, grabbed the lube, and approached me from behind. She demanded that I get off the table, stand up, and bend over. I obliged her every request, and before I could even gather my thoughts or guess what she what about to do, she slid her tongue deep in my ass again, spitting on me and lubing me up.

After eating my ass some more, she edged in behind me, slid that dildo deep inside of my ass, and began pumping me hard. Thrust after thrust slid deep inside of me because she wasn't doing it lightly or gingerly. She had that dick so far up in my ass, I thought the tip was hitting my stomach. I moaned and groaned, swayed with her movements, all while wishing it was longer and thicker to fill me more. I came hard as she fucked me with it while my arms were spread way out across the table and my tits were pinned under me.

Just after I came again, Amber barked out to me, "Say it! Fucking Say it."

I didn't know what she meant at first, but then it hit me.

I screamed out, "I am a lesbian, and I love it in the ass."

"Yeah, you do bitch," she snapped out.

Amber reached her arm around me and cupped my pussy tightly in her hand. She then snapped out, "Whose pussy is this?" As she squeezed it hard.

"It's your pussy," I cried out.

"And this pussy belongs to who?"

"It belongs to you." I cried out.

"Whose ass is this?" She barked, just as she slid the dildo as deep into me as she could.

"It's your ass," I squeaked out, barely breathing as I was forced over the table more by her weight and thrust.

"Good, I'm glad we got that clear," she spoke out softly as she started pumping my ass deeper and deeper.

I was almost in tears from the pain and discomfort of being nailed in the ass this deep and as long as she was giving it to me. But I stood there bent over that table, taking that dildo like a good woman should while her fingers rubbed so hard on my clit that I thought I had caught on fire. I think I literally shit myself when she finally withdrew it as she reached around me and fingered me from behind to another orgasm.

I could not believe we had that much sex over the course of the night and morning hours. Of course, we had to get dressed and straighten up because it wasn't too much longer until the kids arrived home, and we had to be presentable. They were thrilled to see her back, and even though neither of us could walk properly for the remainder of the day, it was beyond heartwarming to see her look at me with the passion, love, and desire I had not seen in a while.

We both crashed hard after dinner and didn't wake up until Monday morning when it was time for work. Just before I left the house, she came running down the hallway, asking me to wait a moment.

"You forgot something," she spoke as I stepped back from the door.

Amber grabbed my left hand, slipped my engagement ring back onto my finger, looked me deeply into my eyes, and said, "I'm sorry I left. I am never leaving again. You need to wear your ring, and I'll put mine back on too."

I gave her a big hug before walking out the door, and I felt a warmth and depth with her that I had not yet experienced. Throughout the entire drive to work, I could feel the ring back on my finger, where it belonged, and I felt proud and happy. I was engaged to the most beautiful woman I had ever known. Hoping from that moment forward, we would be together forever. Wedding bells were in our future, but not before we had some work to do.

And some very kinky sex in some very unusual places... I'll tell you more in the next chapter.