Samantha's First Experience Pt. 11

Samantha Pt 11

Please go read part 1 through 10 before reading this...

Kaitlynn starts her journey.

Just as school was letting out for summer my mom called me and told me her cousin Sharon and her youngest daughter Kaitlynn were coming to stay with them while over the summer. Seems Sharon was laid off from her job and was moving in with my mom and dad to take a summer job at the docks and bringing her youngest daughter with who was hoping to find summer work as well. I have probably only seen Sharon three or four times in my life. Sharon was married to Tony (the proverbial) high strung, drunk, violent, abusive husband. Sharon and Tony had three children from the marriage and after years of abuse Sharon left him. They lived in St. Louis and when Sharon lost her job, her and her youngest daughter Kaitlynn who was 19, decided to head south for new opportunities. Kaitlynn had just finished her first year of community college and was the wild child of the family, following right in her father's footsteps with drinking, partying and acting out.

A week or so later my mom called and told me their summer guests had arrived and told me to come for dinner. The last time I saw Sharon was probably 8 years ago and Kaitlynn was very young, so it will be nice to see them again. When I walked into the door, I greeted Sharon and shortly after greeted Kaitlynn. Kaitlynn was hiding in the three seasons room wearing her headphones trying to avoid the family and treachery of being in a new place. Kaitlynn had grown into a beautiful young lady. She was about 5'7 inches tall, thin build with an impressive set of tits. Her ass was round and tight and I instantly had an attraction to her, but since this was "somewhat" my mom's family I didn't think more of it than that. While at dinner my mom asked me if I could get Kaitlynn a job at one of the public school's summer camps as a counselor, so she could make some money and have a job. I told my mom, "I'll see what I can do."

I pulled some strings at school -- through the summer camps -- and managed to get Kaitlynn a job. She would be working Monday through Friday with weekends off and would meet some people her age to associate with. I also work the summer camps a few days a week myself for some extra money so there was a few days Kaitlynn and I might work together. Over the first few weeks of Kaitlynn being in Florida she kept her distance from me, but one night she opened up to me a bit and a great friendship developed. Since Bobby and I were pretty much done, Kaitlynn would ask me frequently if she could come stay with me on the weekends, because she didn't like my parents' house and she and Sharon did not get along well. I was leery about it at first, but finally one Saturday night I gave in and let her crash in my second bedroom. Over the remainder of the summer Kaitlynn was by me from Friday night through Monday morning.

One Saturday night she asked me if she could go hang out with a few of the teenagers that lived in my building and hang around the pool. I said yes and told her to behave. I laid in bed that night just watching TV when an urge came over me. I knew I'd be alone for a while, so I pulled out one of my lesbian movies and threw it in. I thought I had closed my bedroom door all the way, but later found out, I hadn't. I laid in bed watching the girls seduce each other getting wet and horny. I slid my shirt off and unhooked my bra, letting my tits fee. I slid down my yoga pants and spread my legs as I become more engrossed in the movie. When I was ready enough, I slid my finger between my leg and started rubbing my clit over my panties. The material made it so much rougher and sensitive usually bringing me to orgasm faster. After a while I slid my panties aside and was rubbing up and down my pussy lips occasionally sliding a finger in and out of me, using my wetness to lube my clit that I was still working on. I brought myself to multiple orgasms as I masturbated.

What I didn't know at the time is that Kaitlynn had come back early and being as quiet as a mouse, let herself into the house, heard moaning from my room and came to see what was going on. She caught me playing with myself and watched for a while before heading to her room.

The next morning after breakfast Kaitlynn asked me, "Sam, are you a lesbian?"

I blushed and giggled saying, "Why would you ask me that?"

Kaitlynn said, "Last night I came back a bit early than usual and when I came in, I heard moaning from your room, so I walked over to see what was going on."

Kaitlynn follow up by saying, "I stared through your door watching you playing with your yourself watching lesbian porn. I saw you getting off on it and I never knew a "straight girl" who masturbated to lesbian porn."

I was embarrassed, at a loss and I didn't know how to respond. I didn't care if she knew, I just didn't want her to be freaked out by it.

I held Kaitlynn hands, looked her straight in the eye and said, "Yes Kaitlynn, I feel I am more lesbian than straight. I have dated women before and don't know where I'm heading to next, but feel I would rather be with girls than boys.

Kaitlynn smiled and said, "I know the feeling."

After some lengthy conversations over the next few days, Kaitlynn confided in me that she feels she would do better with women than men. I urged her to try to seek what makes her happy, but wasn't going to push the issue.

The following weekend -----

Late Saturday night I was in my bed wearing my usual crappy loose T-shirt and comfy shorts watching the late show when Kaitlynn knocked on my door. She came in and sat on the edge of my bed and asked if we could talk more. Kaitlynn was wearing her little high school style cloth daisy duke tight shorts and a t-shirt without a bra, with her hair in a ponytail. Anyone in sight on his nighttime ensemble would be ready to pounce all over her.

Kaitlynn sat down and said, "Sam I have a confession."

Kaitlynn admitted to me, "You know last weekend when I came home early and caught you masturbating. I didn't leave right away. I stood there and watched you and watched some of the movie getting turned on." Kaitlynn followed up by saying, "I got so turned on that I was grabbing and cupping my tits and was just about to start rubbing my pussy when you got up and to shut the video off. Kaitlynn followed up by saying, "Once I went to bed, I couldn't get those thoughts out of my mind, so I masturbated in my room."

Kaitlynn dipped her head in embarrassment and babbled on for a few minutes beating around the bush, but finally mouthed the words, "Sam, I think I'm a lesbian too. But I haven't had a lot of experience."

Kaitlyn and I sat and talked about her sexual experience for a while and I learned she wasn't a virgin and had a few boyfriends during high school, but also had some very hot and erotic make out session with girls her age, but never full out sex.

Kaitlynn says, "Can I sleep in here with you tonight? I don't want to be alone."

I was very hesitant at first, but agreed. During our lengthy chat, Kaitlynn asked how I had my first experience and who I had been with? I told her my first experiences were kissing girls in college, but I didn't think much about it because it was just being flirty and horny on nights while drunk at the clubs. But then I told her how I met Jennifer and the lust and desire I had for her, that I finally went through with my first sexual lesbian experience and how I became absolutely enthralled by it. How nervous I was, but how easy it became once I realized how much fun I was having, especially after I developed feelings for Jen. How Jen and I helped Ashley out and how sexy and erotic that night was. How I met and fell "in lust" for Anna and my experiences with her. To be honest, sitting there talking to her about my experiences, hearing some of hers and knowing she was leaning towards women; I was so fucking excited, turned on and horny that I didn't know how to handle the situation. I am not related to Kaitlynn and she is very young, but I wanted to fuck her. I asked Kaitlynn, "Do you want me to put on a video and you can watch it to see if you like it?"

Kaitlynn replied, "Yes" and got excited I suggested it.

Kaitlynn situated herself on the right side of my bed pulling the blankets back, lying on her back with her head resting on some pillows which were propped up against the headboard. I grabbed a soft romantic lesbian movie and put it in. The movie started to play as I climbed back into bed, I told Kaitlynn, "Don't be embarrassed and if you have any questions, or comments just ask."

Kaitlynn and I sat watching the movie and about mid-way through the second scene I can tell she was getting turned on. She was absolutely affixed to the two actresses making love. I myself was so fucking wet and horny, but I didn't want to push an issue or make a move if this girl was unsure. Out of the corner of my eye, I watched Kaitlynn's hand slowly slide her shirt up revealing her stomach. Her hand rubbed side to side and along her body as she became more engrossed. I figured she wasn't going to make a move, unless I led the way, so I leaned forward and pulled my shirt up and over my head. Kaitlynn's eyes light up as I exposed my tits. I started cupping and caressing myself. As Kaitlynn sat watching me, I said, "It's okay of you want to masturbate."

Without hesitation, Kaitlynn lifted her shirt up past her neck -- leaving it on -- but exposing her tits to me. They were perfect. Young, ample, perky with light brown nipples which were already hard and excited. I watched Kaitlynn rub her tits, cupping and playing with them as I played with mine. Kaitlynn eventually slid one hand back down towards her stomach rubbing lower and lower with each pass. She lifted her hips and slid her tight shorts off revealing her hot white sexy thong. I about exploded seeing her in her panties. I watched as Kaitlynn's hand slide down into her panties and I watched as her hand circled around her clit.

Kaitlynn spread her legs a bit as I listened to her breathing get heavier, seeing her fingers working faster on her clit. I wanted to slide my and down into her panties to help her finger herself, but I didn't want to push her further than she wanted to be. The third scene brought me to excitement levels I had not been in a while, couple with watching Kaitlynn masturbating next to me. My pussy was throbbing, soaking wet and my asshole was open and awaiting a hard cock. I slid my shorts off, keeping my panties on -- but only for a minute or two -- until I couldn't take it anyone and slid those off too. Kaitlyn lifted her shirt over her head and continued rubbing her pussy at a quick pace, while I was diving two fingers deep inside me. Kaitlynn's attention shifted to me as I slid fingers in and out of myself, as she continued rubbing her clit and up and down her pussy lips.

I whispered to her, "You can take your panties off if you want."

Kaitlynn shly'ly lifted her hips sliding them down to past her knees. She kept her legs closed for a good portion, opening them up only enough to slide her fingers up and down between her legs. I got my first glimpses of her shaved clean young cunt as I continued fingering myself.

I moaned out, "Finger yourself Kaitlynn."

Kaitlynn was unsure of how to really how to use her fingers inside herself and on her clit to bring herself to higher and harder orgasms, so I told her, "Just watch me."

I spread my legs open further and turned my attention back on the movie. My hands and fingers going back and forth from rubbing my clit, to sliding fingers deep inside me, then using my wetness to lube and rub my clit again. I watched Kaitlynn as she mimicked me. I came at least twice, before I finally watched Kaitlynn bring herself into her first big orgasm. I told her, "Keep rubbing it sweetie, make sure you cum again."

I was bursting at the seams watching this extremely sexy, hot, young woman, finger herself next to me. I was in awe that she trusted me enough to take her first steps. Just watching her little finger sliding in and out of her tight pussy, seeing the wetness on her finger, hearing her moan, listening to the actresses on the TV moan, all while my pussy throbbed and begged to be played with was almost heavenly. I came two more times while watching her and I hope she loved the sight of seeing my fingers diving in and out of my sloppy wet pussy.

Kaitlynn and I watched all four scenes on the video - a good hour of porn -- getting ourselves off. Just as the movie was finishing and she had orgasmed for the second time, I leaned over and I kissed her. Our lips just softly touching at first, but then parting as I felt her soft tongue enter into my mouth. She was shaking and clearly nervous, because her kiss was shy and reserved, but she was surely kissing me back deeply and increasingly her passion. Her hand still cupped and caressed her wet pussy as my hand caressed her face. It ended up being a long deep passionate kiss that turned me on even more. I cupped her breasts and softly caressed them as our kiss continued. I was dying to slide down on the bed, climb in-between her legs and eat her out, but I know she was scared and shy and probably just not ready for that yet. We kissed for the better part of 10 minutes just huddling in close and getting our bodies acquainted with one another. I wanted so much more and I think she did too, but it was her first "real naked" experience, but I didn't want to push her further than she wanted to go.

As we broke from our kiss and came down from our orgasms, I shut off the TV and the lights and pulled the blankets back over us. Kaitlynn laid her head on my chest as I wrapped my arm under her head. I felt her breathing on my breasts and on occasion her hand would softly caress my chest and tits. She fell asleep pretty quickly naked, warm and spent, while I laid there with a throbbing pussy, horny as hell wanting more. After Kaitlynn rolled off of me, I curled in behind her spooning her naked body.

As much as I tried not to seduce her, or even think of her that way; the horny devil inside me, heck both of us, won tonight!

As I laid behind her cuddled in, I started thinking that I just seduced this incredibly hot sexy 19-year-old girl as we masturbated together, guiding her through her first steps into lesbian sex and how much more I wanted from her. What was next I wondered??? I feel asleep hoping tomorrow wasn't going to be awkward for her and that she would not feel shy or embarrassed about what happened. I didn't count my chickens to soon on this one, because I wasn't sure if anything would happen again. But I promise you it did!

Kaitlynn and I had a wonderful summer. I showed her all about lesbian sex and spent a whole lot of time eating her pussy out, as she did mine. I even fucked her with a strap on, she fucking loved it. And she returned the favor and fucked my ass hard with it... Which by the way, I fucking loved!

I'll tell you about some of these things in the next chapter. But more importantly, just as summer was ending down, I reached out to Ashley and her and I hooked up. And haven't stopped hooking up since.

To Be Continued...