Samantha's First Experience Pt. 02

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An unbelievable first time experience.
4.1k words
4.72
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Part 2 of the 22 part series

Updated 06/10/2023
Created 10/29/2020
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Samantha Pt 2. A Christmas to remember...

Read Pt 1 before moving on to this story.

Since our first sexual night together I have thought a lot about Jennifer. We have talked and texted back and forth, but with the last few days of school, followed by the upcoming holidays, we haven't been able to plan any time together. I actually feel bad, I don't want her to think this was a one-night thing or that I used her for sex. Although I am really not sure what this is? Or was? Or where this is going. I had fun, I experienced something new, but I don't know if I want a girlfriend or a female fuck buddy. But yet, I am fascinated by her and want to have sex with her again. My mind goes back and forth.

Due to family commitments for the holiday, I will not be able to see her this week. You see my family is very religious and we have a big Christmas Eve dinner, followed by midnight mass, then home for breakfast and off to bed. Christmas morning is a late brunch and presents. Followed by a big Christmas family dinner. Then over the next day or two another family dinner with the other side of the family, so holidays are hard for me to get away.

Jennifer asked me several times to meet over the week, but with this ridiculous schedule I have around the holidays, it's hard for me to get away. Fortunately, Christmas falls later in the week, so hopefully I will be done by the weekend. I ask Jennifer to hold off until later Saturday or Sunday so we can actually spend some time together. Jennifer says she understands, but I am sure she's disappointed.

Late evening Christmas Eve, I am at my parent's house waiting to go to church when I hear my phone go off. I get up to see I have a picture message from Jennifer. It is her lying in bed, wearing a Baby Doll Mini Bodysuit and a Santa's hat asking me if she can CUM down my chimney? I was so excited and so shocked. As I stared at the picture enjoying the view, I realized I'm at my parent's house, with family around. I went into panic mode. I quickly exited the message screen, turned my phone off and rammed it deep down in my purse. My mom asked me if I was alright, because I guess the look on my face was of absolute horror. I hadn't told them about Jennifer, never was planning on it, and now to get this picture while I'm at my old house with family around, at this precise moment, was something rather scandalous to me.

I told my mom, "I was fine; it was a stupid message from a drunk friend" and played it off like it was nothing.

As we sat in church I started to think of Jennifer, the picture she sent and our first night together. I drifted off into deep thought of her kiss, our cab ride home from the bar, when her hand was rubbing up and down my leg. How horny I was, how my pussy was throbbing to be played with. How erotic that night was! As my mind wandered deeper, my body started aching for more. Right there in church I started to get wet thinking about pussy. I was so entranced in thought that I missed the whole congregation standing up for hymns. My mom literally smacked my shoulder, bringing me back to reality. Even as I was singing, I was thinking of Jennifer fingering me, licking my pussy and bringing me to orgasm. After church we went back to my parents' house, it was late and I wasn't going to drive back to my place, so I ended up sleeping in my old room. It was weird lying in my old bedroom after months of being out on my own. How small and inconsequential this room seemed. How I laid in this bed throughout my childhood day dreaming of a million things. I dreamed about boys, about friends, school, my wedding day, my perfect house with the perfect family and yet just a bit ago I was in church thinking about Jennifer.

I remembered I had that picture she sent earlier. I reached into my purse, retrieved my phone and went back to her picture message. She was so cute lying there in her red teddy and Santa's hat. I starred at that image for quite a while. I finally replied to her, "Sorry for the late response I was in church. I loved the picture and wish you could be CUMMING down my chimney."

It was very late so I didn't expect a reply. As I closed my eyes, I kept thinking about what I would do to her if I walked into my room and found her lying on my bed that way. My stomach started getting those butterflies again, I felt the desires I had for her just more than a week back. I slid my hand up and under my T-shirt and started rubbing my stomach. My mind drifted off to kissing her lips, hearing her voice in my ear, sucking on her beautiful tits, feeling her wet pussy in my hand. Seeing her face between my legs licking my pussy. I slid my hand upwards and started rubbing my breasts, stopping at my nipples to pull, twist and tease them. Eventually I couldn't take it anymore and slid my hand down into my panties. I was rubbing my clit in a deep slow circular motion, as my mouth opened with pleasure. I had to be quiet, but I needed to cum. It didn't take me long thinking of her and I brought myself to orgasm. I wanted to go longer, I wanted to cum more, I wanted to start fingering myself. I wished I was at my place alone, so I could get my dildo out and slide it in and out of my wet pussy. And then deep in my ass. Oh, my ass!! It's been so long since I have had cock, I want to fuck her again, but I need to get fucked.

Saturday night brought dad's side of the family to my parent's house. A host of aunts, uncles and cousins all gathered for the big family feast. You know us good Catholic's dressed in their Sunday best all enjoying the holiday spirit. When the night was over, I couldn't wait to go home, get out of these clothes, fall into bed and just get the Christmas week behind me. After arriving home, I changed into something comfortable, fell into bed and I slept very deep and very long into Sunday morning.

After waking up, I got up and took a long hot shower and just soaked my sore achy body, trying to revitalize my spirit. Afterwards, I just put on a pair of soft silky thong panties and my robe and wandered to my kitchen. Coffee!!! I need coffee. I wasn't in my kitchen 5 minutes when I heard a knock at my door. I just knew it was my mom or dad, who were going to make me go to family breakfast. I tied my robe and walked to my door, looked out my peep hole and saw Jennifer outside my apartment. My heart leapt. I whipped open the door in shock that she was there.

"What are you doing here?" I exclaimed!

Jennifer said, "I was on my way to the gym and decided I wasn't in the mood to work out."

Jennifer stated, "I know you've had a few long days, so I thought I'd swing by with some coffee and bagels to surprise you'"

Jennifer held up her hands which were carrying a bag and two large coffee's. Well she was right; it was a great surprise.

I was so amazed and heart touched and of course, I invited her in. We had a brief hug at my door and we walked to my kitchen. Jennifer was dressed down, she had on a large longer white T-shirt on, with dark blue yoga pants and flat white gym shoes. She didn't have much make-up on but still looked absolutely beautiful. It was so good to see her. As we ate, we talked about my family gatherings and what she had done over the last few days with her holidays. She was so sweet for me bringing me breakfast and wanting to take care of me. I was nervous she was there, because this is the first time she has been at my place, but I was relieved I finally got to see her. I wasn't sure anything was going to happen, or even if I wanted it to, but I was happy she stopped by to bring me a much-needed pick me up. Either way I was so glad she had thought enough about me to surprise me.

As we talked, I couldn't take my eyes off of her and even though she wasn't all dressed up, she was still so stunning and sexy with a smoking hot body. I remembered the picture she sent me and now I was envisioning her wearing that instead of these yoga pants. I remembered masturbating to it thinking of her and was wanting to tell her, but I kept that to myself. Jennifer could tell I was still very drained from this last half a week of Christmas monotonous, so she gave me a big hug. We stood in my kitchen cheek to cheek sharing a nice comforting moment. As we embraced, I started to get those tingly, nervous butterflies in my stomach. Suddenly I felt that want, that need, that sexual desire like I had on our first night.

I wanted to hold her longer. I wanted to kiss her. I realized how bad I wanted her. I leaned further against her just giving her a bigger longer hug, just finding comfort and release in her arms. I felt comfortable holding her. I needed her embrace. As we pulled way, we held hands and just stood there face to face. I gave her a long soft closed lip kiss. I felt my stomach doing flips. We both edged closer, starred into each other's eyes, slowly leaning in towards each other and our lips met again. This time the kiss turned from a soft kiss on the lips to a full-blown French kiss. We were standing there kissing passionately. I could taste the coffee on her tongue, her smell was intoxicating, even without perfume. My mind raced because I was deeply engaged in a heated kiss with this beautiful woman in my own apartment. It got me even more excited.

After a few moments of intense kissing I knew I wanted her. Right here, right now! I couldn't take it anymore. There was no time for a couch or bed. I wanted her right in this kitchen. My pussy was already pulsing. I broke from out kiss and I lifted Jennifer's T-shirt over her head, throwing it on the ground. A smile came across her face. I reached out and pulled down the cups of her bra down exposing both her tits. I grabbed one of them with my hand as my mouth moved to the other one. I started softly sucking on her nipple. My tongue swirling around it, sucking on it, making "popping sucking sounds" as I worked her nipple. I switched over to the other tit and continued pleasuring her. I felt Jennifer reach behind her and unsnap her bra, throwing it on my counter. I stood back up meeting her face for another deep kiss. I felt her untie my robe letting it hang open and loose. I felt her hand on my stomach. I quivered, as her warm hand worked her way up to my tits. Her hands swirled back and forth between both breasts running her fingers and hands across my nipples, pulling them, teasing them. My pussy was throbbing. I wanted to eat her pussy out, I wanted her mouth on me. But I also needed to be penetrated. I needed to be filled.

Without breaking our kiss, I put my hands-on Jennifer's hips and slid down her yoga pants and panties are far as I could push them down. She stepped out of her shoes as I reached my hand in between her legs to feel her completely hair free pussy. She shaved it and it felt so sexy. I rubbed up and down her pussy, just feeling her sensual body wanting to make her wet. I felt Jennifer's hand start rubbing up and down my pussy over my thong. The smoothness of my panties made it more intense. She was using her fingers to rub my clit, making me even more excited and more week in the knees. I felt Jennifer trying to get her yoga pants off using her legs and her feet. We never broke the kiss as she finally managed to kick them off.

I hinted to her, as I started lifting her along her ribs that I wanted her on the counter. Jennifer smiled and picked herself up, landing her ass on my island counter. Her knees were up and her feet rested on the edge of the counter. She spread her legs apart, exposing that hot wet pussy I wanted. Jennifer leaned back onto her elbows as I began kissing down her inner thighs. I dipped my body and head down further in-between her legs. Her pussy looked amazing, all shaved, clean and fresh, getting wet with anticipation of my mouth, tongue and fingers. I dove right into licking her. I ran my tongue up and down her lips, licking and swirling around her clit. My mouth engulfed every inch of her hot pussy. I was going to make her cum and make her cum hard. This time I wasn't nervous, this time I wanted that pussy! I wanted this!

My mouth covered her clit, deeply sucking her while my tongue swirled around it, listening to her ever-increasing moans. You could hear the sucking sounds filling my apartment. Sounds I had heard when my boyfriend's ate me out and now, I was doing it to her. I could hear Jennifer's breaths getting heavier and her moans getting louder. I slid down my panties and dropped my robe. I used my hand to rub my pussy and even played with my asshole. I brought Jennifer to her first orgasm and didn't even stop. I just kept licking and sucking her pussy as she screamed in pleasure. Jennifer's back arched, her hands grasping her own tits as I stuck my tongue as far as I could up into her. I wanted this pussy, I wanted her, I have wanted this for the last few days, I was going to enjoy every minute of slurping her pussy. I was tasting every bit of her pussy. My face soaked with her juices, my pussy dripping. I was becoming a lesbian and I fucking loved it. As I continued eating her out, Jennifer was moaning and groaning as I was tongue fucking her; all while my fingers were slamming in and out of my wet pussy.

I pulled my face back to see Jennifer in absolute pleasure, our eyes met, my pulse quickened. I stood up straight in-between her legs and I slid two fingers deep inside her. I watched her every move, hearing her every moan as I finger fucked her hard. Jennifer's face filled with lust and pleasure. I stood in awe, just starring over her hot sexy body as my fingers slid in and out of her pussy, her body quivering, hips moving back and forth because I was bringing her to orgasm.

Jennifer was moaning out, "Don't stop, don't stop. I'm going to cum again."

I pushed my fingers inside her as hard and fast as I could, watching, waiting for that orgasmic explosion. Finally, with an open mouth and arched back, Jennifer had a second more fierce orgasm, screaming in pleasure. Jennifer reached down to stop my hand from thrusting back and forth. Jennifer was breathless, shaking and drenched with her own juices and cum.

I pulled my fingers from her dripping wet pussy and placed them in my mouth. I wanted to lick her cum off my fingers. She watched me as I slid my fingers in and out of my mouth tasting every bit of her juices. Jennifer licked her lips, leaned forward and pulled me in for a deep sloppy kiss. Licking my lips and around my mouth tasting herself. I had never seen someone so relieved after cumming. Jennifer sat with heavy breath stating, "That was amazing!"

Jennifer pulled me in again for another deep kiss. She slid down from my counter and we both embraced for a long warm hug. Our naked bodies pressed against each other. I was in astonishment. We held each other and kissed even more deeply. WOW!!! I can't believe this just happened again. I am in my apartment days after Christmas eating this girl out and wanting her to be here. Wanting more. Wanting to pleasure her and have her pleasure me.

Jennifer took me by the hand and walked me over to the couch saying, "Your turn."

Before she could sit me down and return the favor, I said, "Let's go to my bedroom, I need you to do something for me."

Jennifer looked surprised and curious and agreed. We walked to my bedroom and I laid her down on my bed as I went to my dresser. Being rather uneasy, embarrassed and shy about It, I pulled my dildo from my drawer. I normally don't share my sexual toys with anyone, but I wanted to have her fuck me with it. I slowly turned around and showed it to Jennifer and said, "I need you to fuck me with this."

Jennifer smiled from ear to ear and said, "Of course I will."

I followed up by saying, "In my pussy, but also my ass too."

Jennifer's eyes got wide as the sky. She said, "You like anal?"

I replied, "I love anal."

Jennifer said, "I've always wanted to try it."

I laid down next to Jennifer on my back. She leaned over and pressed up against me. She started kissing me deeply. I was already soaking wet and ready for her. Her hand slid up and down my chest, past my stomach eventually reaching my pussy. Jennifer's lips were amazing! So soft and gentle as she kissed her way down to my pussy and started flicking my clit with the tip of her tongue. What a tease! I was in absolute heaven. I felt her warm wet tongue swirling on it as I felt her fingers rubbing up and down my wet lips. She slid a finger in me and I gasped. I could feel her pinky finger hovering around my asshole making me want her to slide that inside my ass. I lifted my knees up, placing my feet on my bed just as she slid a second finger in me as her tongue continued to lick and suck on my clit. Jennifer licked and fingered me to two orgasms before I even knew it. Wow, she is amazing at this!

Jennifer pulled her face away from my pussy and asked me for some lube. I reached into my night table drawer and handed it to her. I knew what she needed the lube for and now I was even more nervous and shy about bringing out my toy. I watched her lube up my dido, spread my legs further apart and slowly start rubbing it up and down my clit and lips. In my mind I was begging her to slide it in me, but worried and nervous about her fucking me with it. She slid down in-between my legs and slowly inserted the dildo in me. At first, she slid just the tip in, but with every thrust pushed it further and deeper into me. The feeling was incredible. I have used this dildo numerous times by myself, but never had a hot sexy woman, slide it in to me. She was sending chills down my spine and getting me off, fucking me with this dildo.

It wasn't long until I was going to cum again. I was moaning deeply, enjoying my pussy being filled with her at the helm ramming it into me.

"OMG Jennifer, I'm going to cum."

Jennifer picked up the pace and withing seconds I exploded all over that toy. Jennifer pushed my legs up to my chest and I felt a dribble of cool wet lube hit my asshole, her fingers rubbing it in, pleasing my asshole. Jennifer slid the Dildo out to my pussy and placed it at the entrance to my ass.

She asked, "Are you ready?"

"Yes", I relied.

I felt the pressure of the dildo entering my ass. I groaned in pleasure. Jennifer slid the dildo in and out of me. OMG! I hadn't been fucked in the ass in quite a while and now I have this big dildo sliding in and out of me. I begged her to go faster and deeper, I was screaming in pleasure. Every inch of my body tingled, my pussy still throbbing. I laid on my back holding my legs up, feeling the absolute pleasure of something long and hard sliding in and out of my tight ass.

"OMG Jennifer, don't stop." I begged her, "Don't stop."

I was moaning out, "Fuck me in the ass baby, fuck me!"

Just as fast as Jennifer made me cum playing with my pussy, was as fast as I was going to cum with her ramming the dildo up my ass. I started thrusting my hips, rubbing my clit and wanting her to do it harder and deeper. Within seconds I was cumming and cumming hard. "OMG" I screamed as I exploded for the third time.

Jennifer withdrew the dildo and climbed up next to me. We cuddled in each other's arms softly kissing and touching as I caught my breath. Our hands softly rubbing each other's chest, bodies and pussies.

Jennifer whispered, "Next time I get the dildo."

I giggled, smiled and said, "Ok."

We spent the rest of the late morning through early afternoon just lying in my bed naked, talking, cuddling and enjoying each other. Of course, we experimented more, licking and kissing and sucking each other off. Becoming closer as friends and as lovers. I think before she finally left, we had both cum 3 more times and we ate each other out at least 2 more times. And since she never experimented with anal sex, I ate her ass out. She loved it! I wanted to fuck her with the dildo and wanted her to fuck me again, but we decided to wait until next time for more toys.

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