Amber The Babysitter Pt 08

I try to start every story from the heart, telling the reader how much excitement, lust, passion, or even taboo desire I had during my experiences. But since I left you on a cliffhanger at the end of chapter 7, I will jump right in.

When I entered my bathroom with the strap-on wrapped in Christmas paper, my heart was racing. We had already made love and decided to move our relationship further. And as much as each of us had used our fingers and mouths to pleasure each other in our pussies and our asses since we had begun dating, nothing we had done was even close to this.

After I got the strap-on adjusted right and wrapped tightly around my hips with the little nude-colored dildo sticking outwards, I opened the bathroom door and asked Amber if she was ready for me.

"Yes." She replied in anticipation.

I opened the door all the way, walked out, but leaned up against the door frame, sticking my new fake dick out and pointing it in her direction.

Amber's eyes lit up, and she sort of nervously giggled. "Oh My," as she rose from the pillows she was lying on.

"That looks like it could be fun." She spoke further as I started walking towards her.

There was a bit of an awkward conversation as I approached the bed because I had never worn one before, and she surely had never been with a woman who wore one, so it was a bit nerve-wracking, to say the least. But after I crawled under the sheet with her and we both started touching, fondling, and playing with our new little toy, the nervousness subsided, and curiosity got the best of us.

When we entered into a deep kiss, I felt Amber's hand slide down across my body, past my stomach, and onto the strap-on (now referred to as my dick) and wrapped her hand around it. I let her take her time, becoming accustomed to holding it and playing with it since it had been a long time since she had held a dick in her hand. And indeed, the first time, I had a dick sticking out from my loins. It was such a wild feeling reaching down and feeling a hard dick sticking up from my crotch while kissing a beautiful woman. It was wild to feel her hand gliding over it on top of mine or just by herself when I let go of holding it.

Amber's head dipped beneath the covers as her body adjusted. I could see her head bobbing up and down, and I knew she was sucking on the dildo. I couldn't feel it in the aspect of pleasure because it wasn't mine, and it wasn't real. What I did feel was her warm hands on my legs, the straps moving along my skin as she was giving me head, her warmth breath emanating on top of my skin, and the excitement of knowing her pretty face was down in between my legs, as if I was a man, sucking my hard dick.

I was so wet and excited. Even though I wasn't "feeling pleasure" the way a man would, there was no doubt I wanted to stick my dick into her and fuck her hard with it. I pulled Amber up from underneath the sheets and guided her onto her back. I rolled on top of her and was trying to adjust my dick so that I could slide it into her wet pussy. After a bit of position shifting and pushing it down, I managed to get it into her. I was trying to pump back and forth as his legs were resting along the sides of my rib cage. I knew I wasn't doing it right, as I felt I was moving more up and down rather than in and out, but she was enjoying it, and I know, just as she did, how it feels when a man's dick is inside your pussy.

We flipped-flopped angles and adjusted ourselves several times, but I wasn't quite getting the hang of being on top of her. I told her, "Maybe we could try it from behind." Amber nodded in agreement.

I slid my dick out from inside of her and lifted myself onto my knees. Amber slid her body out from underneath me, flipped herself over, raised her ass in the air, and lowered her torso as she prepared herself to be fucked from behind. I reached down and grabbed a firm hold of my dick, edged in closer to her by knee walking myself forward until I was right behind her. I fumbled a bit, holding it and trying to find her opening, but eventually, I felt the tip of my dick right at her slit, and I pushed it in. I edged just a bit closer and started slowly pumping my dick in and out of her.

This time, my momentum and hips were swinging better. I was sliding in and out of her, like a man would be. I grabbed hold of both of her hips, and even though I couldn't feel anything arousing, I knew that dildo was penetrating her deep because her moans and groans were increasing, her hips were swaying with mine, and I could see it sliding in and out of her tight wet pussy. I pumped her to her first orgasm, lying my chest upon her back, holding her while my dick was still deep inside of her. I could feel her body quivering and the warmth of her body upon my chest.

I let go of her, came upright, and slowly started to slide in and out of her again. I looked down and watched as my dick slid in and out of her pussy. The more I began to get the right speed and swaying motion, the more I realized why men love fucking women. It was so hot and erotic seeing a dick that wasn't even real sliding in and out of her tight wet pussy. It made me tingle, knowing my dick was pleasing her. Her sexy ass was in the air, her torso leaning downwards, her moans and groans increasing, her sexy ass cheeks wide open, her tight little asshole looking up at me as I pumped her steadily.

I wanted Amber to experience double penetration. I wanted to be fucking her in the ass at the same time that my dick was in her pussy. I pulled my hand from her side and started rubbing my thumb around her asshole. I could tell my touch was tantalizing her just as much as my dick was. I pulled my fingers from her and took a mouthful of saliva, placing it on my pointer and middle finger, and started sliding it up and down and all around her ass to get it wet and slippery.

When I felt she was ready, I slid my finger inside her ass while my hips were swaying back and forth. As I pumped her with my dick, my finger was pumping her with opposite motion, to slide one in one spot as I was sliding out of another. Amber came again, and her body shook while my dick was deep within her, and my finger was pushed way up into her ass. I was overly excited, and I could feel my wetness running down my legs as I heard her chirp and whimper as that second deep, hard orgasm left her body.

I knew from her previous experience Amber had never been fucked in the ass by her boyfriends. But with all the anal play we had conducted during our time together, I knew she wouldn't be against trying it. I pulled my dick from her pussy and saw it glistening with her wetness. I spit on my fingers again and put more saliva around her asshole, stroked my dick a bit, and guided her hips down. I edged up to the right spot, put the tip of my dick at her asshole, and after a few misses, I managed to slide it inside of her.

Her chirp was the loudest I had ever heard her make, and I knew the sensation of a dick being slid inside of her ass versus my fingers was larger and with more girth than she ever had before. Her body tightened, her back arched, and her breath stopped momentarily as I slowly slid my dick all the way in. As I started sliding it back out, she groaned out, "Lube."

I pulled it out, leaned over her, and practically fell off the bed, trying to get the lube from my nightstand table. I edged in behind her again after I retrieved it. I squirted a bit around her asshole and was working it in with my fingers as I slid them in and out of her. I squirted a bit more on my dick and stroked it to get it all lubed up.

I put the tip of my dick right at her entrance, and this time, it slid right in without missing. I slowly pumped her ass with my dick, just to let her get the sensation of having something inside of her. As time passed, I could see her muscles relaxing, her body easing down, and even though I'm sure she was nervous and unsure, she was going along with it.

I pumped Amber with my dick, slowly and steadily, as I watched it slide in and out of her tight ass. I felt she was enjoying the new sensation and experience of her first anal, but I also knew from my experiences that the pussy needed attention too. I reached around her legs and under her body and started rubbing her clit, swirling my fingers around it as I continued sliding my dick in and out of her. She moaned in pleasure as I continued to penetrate her as lovingly as I could.

I could see her fingers had grasped handfuls of sheets, and I believed she was on the verge of another orgasm, but the harder and deeper I pumped, the more she seemed to drift away from orgasm. I didn't want to make her first experience painful or discomforting. Just as I thought about stopping, her moans and groans increased. I grabbed hold of her hips and started pulling her ass towards me as I was pushing towards her. I barked at her to play with her pussy, and I saw her arm swing under her body, and I could tell her fingers were circling her clit.

"Do you like my dick in your ass?" I asked her.

"Yes!" She chirped out as her legs started to shake.

"You wanna cum with my dick in you?" I inquired of her.

"Umm, Humm," She squealed out.

Seconds later, I was pumping her as hard and as deeply as I could while her fingers were tending to her pussy.

"FUCK!" She cried out as orgasm number three released from her body.

Her back arched, her legs shook, and her mouth kept spewing out little chirps, quips, and groans as she had another hard, deep orgasm.

I leaned down over her and wrapped my arms around her body, feeling the sweat she had released as I kept my dick deep in her ass. My face was resting on top of her shoulder blades. I could feel her breathing in and out. I could feel my heart beating loudly in my chest, as I was sure hers was inside her chest. Amber trembled and shook, coming down from the explosion she just had. When she finally calmed down, I slowly slid my dick from her ass as her body went limp, falling over onto her side, hearing her moaning out words like "Wow" and "Oh My God."

I lay next to her, holding her from behind, my chest pinned against her back, feeling her breathing returning to normal and feeling the wetness of her skin while I softly kissed her head, her neck, and her shoulders.

We didn't say much as we lay together; I just basked in the warmth of her calming down after being fucked hard in her pussy and her ass. Amber fell asleep quickly. She was undoubtedly exhausted after experiencing something new and different from what we had known. Just before I dozed off, I slid the strap-on off, went into the bathroom, washed it off, left it on the basin, and crawled back into bed with her.

I adjusted the covers over her so she was well-covered, warm, and comfortable. I edged in behind her and felt the warmth of her skin against mine as I gently held her. I was still horny, and I wished she was awake so we could have another round of sex. My pussy was throbbing, wide open and wet, but instead of waking her for sex, or fingering myself, I just closed my eyes and kept visualizing that dildo sliding in and out of her while she moaned in pleasure. I was spinning the ring she brought me around my finger in amazement and excitement, knowing we were moving forward with our lives together after tonight. I dozed off with my chest pinned to her back, naked, warm, and absolutely in love.

I awoke before Amber, as I usually do. I got up, brushed my teeth, washed my face, and threw on my robe. I stumbled down my hallway into the kitchen to make coffee. It was a while before I heard Amber get up. When I knew she was awake, I wandered back to my kitchen counter and prepared a cup of coffee for her. When she came up behind me, she wrapped her arms around my waist and whispered, "Good Morning."

"Good morning," I replied. "I hope you slept well."

"I did," she replied. "I was so tired after last night," she added.

Amber held me tightly. Tight as she ever had, and after I set her cup of coffee down, I wrapped my hands and wrist over her arms as she embraced me tightly.

Amber whispered to me, "I love you."

"I love you too," was my reply.

She squeezed me tighter than she was already doing and softly kissed the back of my head.

What I didn't know was that when Amber got up and washed up in the bathroom, she had the idea to put on the strap-on, and she was wearing it under her robe. After she pulled herself from hugging me from behind, she spun me around and started kissing me deeply. She was full of lust and passion as we stood in the kitchen. As the exchange grew hotter and more involved, she untied my robe belt, letting my robe fall open as her hands started wandering all over my skin, along the sides of my ribs, and across my tits.

I became just as turned on as I was last night, and before I could even start returning the favor of touching her bare skin, her fingers were right between my legs as her hand was caressing my pussy. When she slid her finger up into me, I just about rose from the floor. My legs spread further apart as I wanted her to keep fingering me, bringing me to orgasm, standing in my kitchen with my ass up against the counter.

Amber whispered through our kiss, "I have a surprise for you."

When she pulled her hand away and opened the belt loop of her robe, the sexy little nude-colored dildo was strapped to her. It was sticking out like a man would be if he was having a hard-on. I could feel it push up against my skin when she pulled me into the body while her fingers kept sliding in and out of my pussy. I was wet, I was aroused, and I was more than ready to take that dick anywhere she wanted to put it.

I got down on my knees and stared at her fake dick, just looking at it, knowing soon it was going to be deep inside of me. I leaned my head downwards and slid it into my mouth. I slid back and forth on it like I was sucking a real dick and moaning out as I felt the hard thickness of it sliding across my tongue and into the back of my throat. I bobbed back and forth on it for a while, looking up at Amber with her perfect, sexy body, messy hair, and tired eyes looking down upon me.

Amber pulled me up from sucking on her dick and spun my body around. She leaned me over the counter, and with some slight adjustment in my height and angle, she slid that dick into my wet pussy. We weren't at the best angle; since I am slightly taller than her, so I spread my legs further apart and dipped down, standing like an inverted V until I finally got at the right height for her to be perfectly in line. After I did, she began sliding it in and out of me better than she had moments ago.

From the get-go, she had a better grasp of how to thrust her hips because even though I did feel it going up and down occasionally, she was moving backward and forwards better than I had. Once Amber got the motion and I was at the right height, she started pumping me full of hard dick, and I loved every minute of it. It had been forever since I was bent over with a dick deep inside of me, and considering I was still horny from the night before, this was a perfect moment for me. I came quickly, as I rubbed my clit while that dick was inside of me, whimpering out her name as she continued thrusting it into me.

But what surprised me the most was after I exploded for a second time, Amber pushed my hips down further, literally spit on my asshole, and slid her dick deep inside of my ass. She nailed it on the first try, pushing it right inside me. Considering all the anal play I have to done in my life, I am not as tight as most women would be back there, so when she lined it up and pushed, it when right in.

I gasped in pleasure and arousal as I felt it slide right in. I moaned out, "Yes, baby, fuck my ass hard."

It was an absolute pleasure as I felt her start sliding it in and out. I was moaning and groaning, trembling and shaking, grabbing onto the other edge of the countertop as she rammed that dick into my ass deeply and thoroughly. I was like nothing I had ever experienced before with another woman. I couldn't have predicted a better morning if I had tried.

The more she pumped my ass with that dick, the more I remembered how much I loved anal. Even now, sitting here writing this now, I am soaking wet remembering the feeling of her ramming that dick deep into me as fast and as deep as she could.

I came time and time again. One right after the other, and the more she was ramming that dick in and out of me, the more I came to understand that this wasn't a man behind me or some sex toy I had bought. This was my lesbian lover, my soon-to-be wife, fucking me in the ass as hard as she could, and it made me want her even more. I didn't even care if she didn't touch my pussy anymore that morning; I just wanted her to keep ramming that dick inside of my ass and make me cum time and time again.

I begged her not to stop. I screamed out in pleasure when I was about to cum. I do not doubt that every time I said, "Don't stop, Amber, don't stop! I'm gonna cum." The more excited she got fucking me.

Pump after pump filled me with feelings I hadn't had in forever. And the more I felt that dick inside my ass, the more I wanted it. I couldn't tell you how long she was fucking me, but I didn't want it to end. For anyone who enjoys anal, as I do, you understand the pleasure of being relaxed and comfortable, surely ready and eager to have your lover fuck you hard as they slide a dick in and out of you. As much as I was enjoying every second, I wished that the strap-on was bigger, longer, and thicker because I wanted it so far up into me that I would be screaming in pleasure and in pain.

When we finally finished, and she slid that dick out from deep in my ass, I tried to stand back upright, but my legs were weak and shaking. I was unsteady and had very little balance. She stood next to me, holding my hand and arms, as someone would for an elderly person, guiding them to their feet. We kissed lightly, and we whispered words of love and devotion. We walked over to the couch, where I lay flat on my back. Amber unstrapped the dildo, slid out of the straps, sliding it down her legs and climbed on top of me. We lay together, skin pressed to skin, and she pulled my big Afghan over both of us. She was so aroused that as she lay on top of me, I could feel her legs rubbing together like a cricket. As we kissed deeply, and I got her hint, I slid my hand in between our bodies, and I slowly and deliberately took my time fingering her until she had a big, deep orgasm.

As we cuddled under the blankets, Amber told me that several times throughout the night, she woke up horny. Instead of waking me up to have sex, she masturbated herself to orgasm and then would fall back asleep. She blushingly and quite shyly admitted she fingered herself while watching me sleep and even had fingered herself in the ass. She said she had cum four times on two different occasions and openly admitted even though her first anal sex was scary and uneasy, she loved it.

Throughout the next six months, our relationship developed even more. She lived with me almost 24/7. There were days she'd still go home and spend a night or two with her parents, but for the most part, she was with me. Our lovemaking was consistent, and our passion for one another grew. Our love blossomed more than I could have ever imagined. And as time passed, we developed our lives around one another. Nights developed into us coming home together, making dinner, helping the kids with homework, and going to bed together as couples do.

By the time she graduated college after her internship, there was no doubt that we were headed for a life together. I had truly digested the fact that I was going to be married to a woman and that I was going to live my life as a lesbian. My kids accepted it. My parents, along with hers, had accepted it. And if anyone who knew didn't accept or understand our love, that was on them. I didn't care. I was in love. I was as deeply in love with her as I had been with men. The only difference was it was her. It was a woman. It was, without a doubt, something I would have never imagined. Even in my wildest fantasies years back, I would have never thought I would have ever felt like I did with her.