Samantha's First Experience Pt. 04

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My continuing lesbian experiences.
4.7k words
4.76
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Part 4 of the 22 part series

Updated 06/10/2023
Created 10/29/2020
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Samantha Pt 4.

Ashley wants to watch.

Please read part 1, 2 and 3 before this...

*

Two weeks have gone by since Jennifer's birthday party and things are moving along as usual. Early March in Florida brings warmer weather, longer days and the uneasy concerns of the up-coming spring break Melees which start towards the end of the month. Since Jennifer and I have said, "I love you" to each other, I have come out to a couple friends. I think it was hard for them to grasp at first, but the two I have told wished me the best. Jennifer has also told a couple of close friends and they are happy for her. Jennifer is staying the night at my house tonight so we decided to order in some food and just chill on the couch watching TV and enjoying our time together. I suddenly remember her friend Ashley from the bar. I remember Ashley seeing Jennifer rubbing on my leg and us whispering to each other and of course seeing us hugging and kissing in the bar parking lot. I wonder if Jennifer heard anything from her about it.

I ask Jennifer, "Hey did you ever hear anything from your co-worker Ashley who was at your birthday party? About us? About what she saw?"

Jennifer says, "She sent me a message the next morning saying, "looks like you two had fun," but since then not a word."

As god as my witness, I must have jinxed us by asking about Ashley, because minutes later Jennifer's phone dinged. She got up to check it and it was a message from Ashley.

The message read; "Hey Jen, I am sorry to bother you and it's not my business, but I have been thinking about this since your party. Are you dating that girl Samantha who came with you to the party? Or did you just have a drunken make-out session in the parking lot?"

Jennifer was at a loss and didn't know how to respond. Jennifer is very uneasy about sharing her private life with people. Jennifer tells me, "I have not told any of my co-workers about us. I don't like to share to many details about my sex life and some people I work with can be gossip queens." Jennifer goes on saying, "Ashley is one of the more tenured teachers and I don't know her well enough to know if she'd keep her mouth shut."

Jennifer tells me, "Ashley in on the PTA, is involved in the community and does work with her church. Ashley's husband is a successful -- well known - business man and they live in a very nice house in the better part of town. They have good friends, good connections and are considered pillars of the community. So, for me to come out as being in a lesbian relationship, may cause friction with her if she doesn't like it." Jennifer chuckles aloud and says, "I think Ashley is strictly heterosexual and probably hasn't even kissed a woman, nor fantasized about a woman, let alone dated a woman and now she's asking me if I am dating a woman?" Jennifer is concerned about why Ashley is asking about this and believes maybe Ashley will start telling everyone at school if Jen admits to anything.

I tell Jennifer, "Respond with what you feel is best. If you don't want to tell her, say no. If you don't want to lie then just admit it."

Before Jennifer can even answer another text from Ashley comes in. It reads; "I am sorry if I am overstepping my grounds and I don't want to pry into your personal life. But I have a dilemma and if you are dating a woman, I may need some advice."

Jennifer looks at me, smiles and says, "Well she's already seen us flirting, hugging and kissing and we are dating. So, if she's already figured it out, how long will it be until everyone finds out? I may as well just admit it."

Jennifer turns her head back to her phone, takes a deep breath and types her reply, "Ashley, I'm going to put trust in you and answer your question. Between you and I (AND NOT ANYONE ELSE IN SCHOOL). Yes, I have been dating Samantha for almost three months now. So yes, I am in a lesbian relationship."

Moments later another message from Ashley comes in that reads, "Cool, I don't care who you date and it's not my business to discuss nor judge peoples dating relationships. But I need to sit down and talk with you outside of school one night. I NEED A FAVOR."

Through further messages Jennifer agrees to have dinner with Ashley later in the week. We are both quite curious on what she needs "advice for" and what her "dilemma" is. But I guess we'll find out.

Thursday night, Jennifer meets Ashley at a local steak house. She stays there for a while discussing Ashley's issues and they part ways. On her way home she stops by my house to let me know what happened.

Jennifer tells me, "Ashley's problem revolves around this. Ashley promised her husband a threesome on his 40th birthday, coupled with an early 10-year wedding anniversary present."

Ashley told Jennifer, "My husband's birthday is in late-April and our wedding anniversary is in early June. So now, I need to uphold my word, but I have never even kissed a girl before, let alone had sex with one."

Jennifer related Ashley is scared and nervous and doesn't even know where to begin.

Ashley told Jennifer, "I know a woman from the Yacht club I'm a member at; who is Bi-Sexual, very attractive and always is coming on to me. But I don't know how to approach her to ask her if she would do it, or if I could even do it. And since you are dating a woman and having sex maybe you and Samantha can show me how to seduce a woman and maybe let me watch you two having sex."

Jennifer said, "It was kind of a big surprise to hear Ashley tell me she needs to have a threesome and ask me if we could teach her how to seduce a woman and let her watch us having sex."

Jennifer said, "I didn't answer her yet, I wanted to discuss it with you first."

What an odd situation. I don't know if I would have ever asked a lesbian couple; let alone any couple, to watch them have sex. I don't know if I would get as turned on by them, or feel uncomfortable watching people I know at their most intimate. Moreover, would I be comfortable and fully engaged knowing someone was watching me? Especially someone I work with whom I'm going to see in the hallway, who just found out I'm in a lesbian relationship and watched me fuck my girlfriend. I give Ashley kudos for having the guts to ask, but in my heart, I fear the worst with this. My initial answer is no, but Jennifer and I go back and forth for days discussing this.

We finally agree to it, but set some ground rules. 1. Neither of us are having sex with Ashley, nor her husband. 2. When the time is right, she can watch us if she feels she needs to do that, but it's only after all of us become much closer. 3. If we're going to introduce Ashley to lesbian sex, then we need to seduce Ashley to the point of her wanting lesbian sex. But, never let her go through with it -- with us -- and let her use what she has learned to seduce and fulfill her desires with a female lover she chooses. 4. Ashley needs to comply with our every request, including watching lesbian porn to see what the performers do and how they get each other off. And lastly 5. No matter what happens, this stays between us.

Jennifer plans a night where all three of us can meet and talk. We all meet and have dinner, sit, talk and just get to know each other more. As we sit with Ashley, we tell her our rules and concerns and Ashley graciously agrees. Ashley asks a lot of questions regarding our relationship. How we meet? When did we knew we were sexually attracted to each other? Do we miss men, or just realized we liked women more? As I get to know her throughout the night, I can tell Ashley is very sweet, caring and compassionate. Ashley is the proverbial 36-year-old suburban soccer mom. She has long brown hair, big (getting saggy) breast, a bit overweight but not fat. She is very smart, very friendly, very curious and is longing to fulfill her husband's desires and keep the promise she made. We all agree to start hanging out after work when we can and hopefully a few Saturday nights, so we can show her what she wants to know. Over the next few weeks, we meet Ashely at bars and restaurants and develop our friendship, try to create a lust for each other and try to make her feel comfortable with us. We hit on her making her sexually interested in us and in women. We flirt with her and make her lust after us. There were many of nights of rubbing up against her, teasing her hair, whispering sexual innuendos in her ear. We would grab her ass, place our hands on her tits and lightly kiss her cheek and neck at any given opportunity. We were doing our best to seduce her, make her feel wanted and make her interested in experiencing lesbian sex.

One Saturday night we got way to drunk at this dive bar and I was dancing with Ashley. I slowly walked her backwards and pushed her up against the wall. When I had her pinned there, I leaned in and kissed her. She was taken-a-back at first but slowly parted her lips. As our tongues met, I felt her arms wrap around my waist. She was kissing me back and seemed to enjoy it. When we broke from our kiss, Ashley's eyes lit up and she smiled. I could see the lust in her eyes and I realized at that moment her fear of being with a woman was going away and her desire to have sex with a women was growing. Before that night was over, she had kissed both Samantha and I several times and I believe she went home very horny and very interested in going forward.

After weeks of seduction and fascination, we picked a date for our night together. We decide to have a nice quiet dinner at a local restaurant, followed by a few drinks at the bar, then back to Jen's house. We all dress down and casually for our night together. I am nervous as can be and can only imagine Jennifer and Ashley are too. We sit at a half moon booth and put Ashley in-between us. During our dinner, we both flirt with her. We place our hands on her thighs and rub up and down. We both kiss her on the cheek and tell her how beautiful she is. We grab her hand and slide it up and down between our legs getting closer and closer to our pussies each time. Ashley is blush red and embarrassed, but I she's feel loving every minute of our attention. Just before we are leaving for the bar, I take Ashley's right hand and put it right on my pussy over my shorts. At first, she starts to pull her hand away, but I put my hand on top of hers so she can't pull it away. I feeling her hand trembling as it sits on top of my pussy. I help her hand start rubbing up and down my shorts feeling the outline of my vagina. Ashley is in amazement. Jennifer sees what I am doing, leans towards Ashley and slides her hand in-between Ashley's legs lightly caressing Ashley's pussy over her jeans. The look on her face was of pure enjoyment. I lightly kiss Ashley on her lips and ask her, "If she's ready?"

Ashley nods her head up and down implying yes.

We leave the restaurant and head to the bar. As the night progresses, I feel Ashley slide her hand across the back of my ass as I take my turn throwing drats. I see the cute smirk on her face. Ashley watches Jennifer and I kiss passionately and sees the love and admiration we have for each other and I think her desires have come full circle and she wants to have sex with woman. As we get more alcohol in us, the passions between all three of us gets hotter. I am so turned on by flirting with her, watching Jennifer flirt with her and knowing that tonight we are going to have this woman watching us fuck each other. As the night draws to a close, we all agree it's time go. We ask Ashley several times, "If she's still good with this?"

Ashley replies, "Yes I am."

We arrive at Jennifer's house and pour some wine. We all stand in the kitchen for a bit nervous and delaying the inevitable, but we all know why we are here. Jennifer takes Ashley by the hand and leads her down the hallway to her bedroom, as I follow along. Jennifer sits Ashley down on a high back accent chair that sits adjacent to the bed. Jennifer leans down and gives Ashley a long, soft closed lip kiss and says to her, "I hope you enjoy."

I put my wine down on Jennifer's night stand and meet her at the foot of her bed. We kiss deeply as I hear Ashley let out a soft loving moan. Jennifer and I climb on to her bed. We are kneeling upright face to face. Our kisses are passionate and sensual. As we kiss deeply, I pull Jennifer's shirt over her head and kiss along the left side of her face, down her neck and onto her shoulder blades. I can see Ashley who is sitting in the chair, affixed on us, her finger is rubbing along her lips, her mouth partially open and her free hand is lightly rubbing up and down her leg. I unsnap Jennifer's bra releasing her beautiful tits. I kiss my way down to her left breast and suck on her nipple. Jennifer's head tips back in pleasure. As I come back up face to face with Jennifer, she slides her hand in-between my legs and starts making her way up the leg of my shorts. I moan in pleasure as I feel her hand hit my panties.

As I look over Ashley is sucking on her finger, while her free hand is now rubbing, cupping and grasping her breast. Jennifer pulls my shirt over my head and unhooks my bra. She kisses her way down my chest and sucks on both of my tits, teasing and pleasuring my nipples. We come back face to face and engage in another heated kiss. Our arms wrapped around each other, our tits pressing firmly against each other. We ease down onto the mattress lying side to side continuing to kiss and touch each other. I see motion out of the corner of my eye and realize Ashley has just pulled off her shirt and is now rubbing her tits over her bra with both hands. Her legs partially spread open just getting more and more excited as Jennifer and I slowly undress each other. Jennifer rolls on top of me and our kisses become more intimate. My pussy is starting to get wet and for a few moments I forget we are not alone. Jennifer pulls away from our kiss and works her way down to my chest. She cups, caresses and sucks on both tits as I moan in pleasure. My pussy is throbbing and I am longing for her tongue and fingers. Jennifer kisses her way down to my shorts and unbuttons them. I feel her pull my zipper down as she is kissing and licking around my belly button. I feel Jennifer's hand slide down my pants and over top of my panties. I arch my back in pleasure.

Her hand softy and seductively runs up and down my pussy, making me hotter than I was before. I reach for the top of her head and just feel her hair in my fingers as she kisses further down. I feel her starting to slide of my shorts and I lift my hips to assist. Jennifer starts kissing up and down my legs, I feel her hair brushing against my inner thighs. I look over and see Ashley's has her hands under her bra cups, rubbing on her tits and her pants are unbuttoned and unzipped. We make eye contact and I can tell she is as hot, horny and as turned on as I am. I see Ashley lean forward and reach behind her, unclasping her bra. She shyly pulls it away from her body dropping it to the floor. Her tits, big heavy and plump now exposed to my eyes. Ashley watches us as she rubs and caresses her tits. She pulls on her nipples making them hard and erect.

I pull Jennifer back up to me and I kiss her deeply, I roll her onto her back and start kissing my way down her chest. I stop to suck on her tits and lightly bite and tease her nipples. I kiss my way down her stomach to her pants. I unbutton and unzip them, making eye contact with her as I do. Jennifer smiles seductively. I can see she is watching Ashley to see what she is doing. I climb on top of Jennifer, pressing our chests together. Her arms wrapped around me, as we continue this slow, soft sensual love making. I slide off to the side and slowly dip my hands deep into her panties. Her pussy is soaking wet and wide open awaiting my fingers. I rub her clit softly and slowly in circles as we continue kissing. I break from our kiss and look over to see Ashley rousingly running her hands up and down her jeans, her mouth open, her tongue licking her lips. Ashely is in clear view of my hand down Jennifer's panties and I think it is driving her crazy. The more she watches me rubbing Jennifer's pussy the hotter she is getting. The hotter she's getting the more turned on I'm getting. Jennifer leans in towards me, opens her legs more and slides her hands down my stomach and into my panties. I moan in pleasure, as I hear Ashley gasp. Jennifer and I both look over and see Ashley has her hand down her pants and she is rubbing up and down her pussy.

We watch Ashley's fingers moving under her jeans and she is starting to moan in pleasure. Jennifer and I slide fingers deep inside each other as we enjoy watching Ashley playing with herself. Ashley's head in thrust back, her mouth open and her moans increasing. I am dripping wet and want to lick Ashley's pussy as much as I want to lick Jennifer's. Jennifer and I lay side to side fingering each other, as Ashley watches us fingering herself. I slide down my panties as Jennifer does the same. I get up from lying next to Jennifer and kiss my way down her sexy body. I climb in-between her legs on my knees bend forward and dip my head to her anxiously awaiting pussy. My ass is in the air and facing Ashley and she now has her first view of my sexy waxed, wet and throbbing pussy. I lick Jennifer's pussy up and down as I see her playing with her tits. I feel her wetness all over my face and I want to bring her to orgasm. I swirl my tongue around her clit then slide my tongue up and down her wide open and wet pussy lips, stopping to put my tongue in her as deep as I can. Just a minute into eating Jennifer out, I can tell she is about to cum. Her moans get louder, her hips start thrusting back and forth and I await the pleasure of feeling her cum on my face. Jennifer starts screaming "I'm going to cum, I'm going to cum."

And with that Jen's body and legs start quivering as she explodes in pleasure. I her Ashley moaning in the background, she is about to cum too. I look back to see her body thrusting back and forth rising from the chair as her hand continues working her pussy. Within seconds, Ashley is crying out in pleasure, "I'm cumming, I'm cumming."

Ashley gasps for air as she releases her orgasmic pleasure. She looks deeply and longingly at both of us and says, "Wow, I don't think I've ever cum that hard masturbating before."

Jennifer says, "That's just the start, we have only just begun."

I slide my way back up to Jennifer's face and kiss her deeply. She rolls me onto my back and starts kissing her way down my chest and stomach. I look over to see Ashley is taking off her pants. She is wearing a cute pair of off-white panties. Ashley is still catching her breath as Jennifer's face slides in-between my legs I feel her tongue hit my clit and it sends shivers down my spine. Ashely is now getting her first view of Jennifer's hot sexy pussy and is starring at it with intense passion. Jennifer starts eating me out as Ashley's eyes are affixed on mine. I see her start playing with her breast again, her legs swaying back and forth, her passion and desires ever increasing. With her right-hand Ashley slides her panties to the side revealing her pussy. She has hair on the top, but it is shaved from the clit down. It looks sexy for a woman that has had two children. I see her start rubbing her clit in circles as Jennifer's tongue is doing the same to me. Ashley's left hand is rubbing and pulling on her nipples getting herself even more turned on. Her legs are spread wide open and she is enjoying playing with her pussy as much as I am enjoying Jennifer playing with mine. Ashley lifts her hips and slides her panties down. She balls them up and put them in her mouth, moaning in pleasure as she tastes herself off of her clothing. Her legs as wide open as she can get them as she rubs up and down her pussy lips. Between watching Ashley masturbating and Jennifer licking my pussy, I immediately start cumming, I can't even get the words out of my mouth before my legs start shaking and I explode with pleasure.

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