Samantha's First Experience Pt. 14

Samantha Pt 14

Please go read part 1 through 13 before reading this...

*

Her first strap on.

Saturday night Kaitlynn and I were lounging around the house because there wasn't much to do, so we decided to have a movie night. We were sitting on the couch watching a romantic comedy, when Kaitlynn paused the movie.

"Sam, I have a question for you," she blurted out.

"Ok Katie, (I always called her Katie) go ahead."

"Do you miss boys at all?" She asked.

"Sometimes I do," I replied. "Why do you ask?"

"Cause, all this summer that I've been with you, which has been incredible, I sometimes feel I miss boys."

"I can understand that Katie. You are young and experimenting, so I'm sure you're going to miss things. There are times I miss men too."

"But Sam, you've been with a lot of women for long periods of time, don't you miss having Penis?" (It was so cute to hear her say Penis).

"Yes Katie, I do miss Penis on occasion, but there are ways around that even with a female lover."

"How?" she asked.

"Well, there are toys and strap-on's that women use to have that, "filled feeling," so that can help. And of course, if you are a true lesbian, then you really don't want men, so the pleasure of being with a woman can fulfill your needs."

"Have you ever used a strap-on?" She asked.

"Yes, of course I have."

"On women, or them on you?" She asked.

"Both," I replied.

Kaitlynn's eyes lit up and her curiosity peeked even further. "Do you have one here?"

"Yes." I replied.

Kaitlynn's face turned bright red and I think she was partially embarrassed but also partially excited.

"What does it feel like? Can you tell the difference?" She asked.

"Yes, there is a difference from a real man, but it still slides in and out of you like a man would."

Did you like it?" She asked.

"Yes Katie, I liked it and do enjoy it from time to time."

"Do you want to try it?" I asked.

Kaitlynn about jumped onto my lap with excitement. "Yes," she squeaked out.

"Okay, maybe after the movie we can try." I blurted out.

Of course, there was no way I was going to make it through this movie, knowing we were going to have sex and that I might get to fuck her with a strap on. Kaitlynn leaned her back and body up against me as we cuddled in closer. I stoked her hair, twirling it in my fingers, as our attention went back to the movie. I know I couldn't focus on anything but her and I was getting so excited. After a while, Kaitlynn leaned her head backwards and looked up at me. We stared deeply into each other's eyes until I finally leaned down and kissed her softly. Our closed lip kiss led to a soft, long gentle French kiss as my hand caressed her face. Kaitlynn, twisted herself around, getting onto her knees leaning towards me as our kiss deepened. Our hands softly caressed each other until I couldn't take it anymore. I edged her off of me and we both got to our feet. I shut the TV off and led her by the hand to my bedroom.

I laid Kaitlynn down on the bed and climbed on top of her. Our kisses increased with passion as we got more entwined with each other. I felt Kaitlynn pulling at the back of my T-shirt. I lifted my body off of hers and helped her pull my shirt over my head. Her hands caressed my breasts over my bra as we continued kissing. I felt her little fingers unclasp my bra hook and I slid it out from under my arms throwing it to the side. Kaitlynn placed her warm hand on my right breast as her mouth cupped my neck. Her tongue swirled around as her mouth moved open and closed. She kissed down my neck towards my chest as I lifted my body upwards. She kissed far enough down to place her wet warm mouth over my right nipple. Her tongue swirled around it, making it hard and pleasured as she sucked it. My hands pulled at the bottom of her shirt lifting it up high enough to slide my hand up to her chest. I cupped her breast over her bra caressing and fondling her tits as she continued sucking on my nipples. I leaned back onto my knees pulling Kaitlynn's body upwards. I pulled her shirt over her head and unhooked her bar. We both fell back into each other as she leaned backwards, letting herself back down onto the mattress. I slid to the side just off of her as I played with both of her tits, keeping our kiss ongoing and heated.

I could feel myself getting wetter by the moment and hoped Kaitlynn was too. I slid my hand down into her sweatpants, feeling her throbbing clit over her tight G-String. I felt Kaitlynn's hand trying to reach down into my shorts. I edged further up so her hand could touch my pussy. We laid together topless, deeply kissing, with our hands down each other's pants touching and rubbing our pussies. During that moment I had thoughts of being in Ashley's car just like this. Topless, with our hands down each other's pants rubbing, playing and fingering each other to orgasm. It got me even more excited to re-live that experience and being with her.

Kaitlynn's body movements and moans brought me back to reality. I was bringing her to orgasm, while fingering her tight wet pussy, making her want lesbian sex more and more. Pleasing her like no one else had. I was soaking wet and wanted every bit of her. I needed to cum, I needed her to eat me out, I needed her to finger or fuck my ass. I was so turned on and horny that I whispered in Kaitlynn's ear, "I want your tongue in me."

Kaitlynn smiled and rolled me onto my back. She pulled down my summer shorts, leaving me lying there with just my cute pink panties on. I felt her hands rubbing up and down my legs, until she reached my thighs, grabbing at the outer edges of my panties. I lifted my ass and hips and Kaitlynn slowly slid the off. She spread my legs apart and laid in-between my legs. Her mouth hit my clit sending pulses of erotic pleasures throughout my entire body. Kaitlynn, looked up at me and said, "Wow you're soaking wet."

Her mouth and tongue swirled around my pussy opening, sliding up and down my lips, sticking her tongue inside me, bringing my closer and closer to orgasm. I grabbed the back of her head pulling her face in closer as I exploded my juices all over the bedding. I was cumming hard and was I dripping wet. When Kaitlynn pulled her face away from my pussy, I could see the glistening of my juices all around her mouth. I pulled her upwards and on top of me and I started licking around her mouth tasting myself, as we began to kiss again. I couldn't contain myself as I tried to push Kaitlynn sweatpants down. I was still throbbing and pulsing and I wanted her pussy, and I wanted it now. Kaitlynn helped me and managed to kick her sweatpants and panties off lying her naked body on top of mine. I rolled her on to her back, got on my knees and kissed my way down her stomach, past her hips and dove my face upside down, into her throbbing pussy. I licked her clit while my eyes looked at her tight wet pussy lips. My fingers rubbing along the insides of her legs. Kaitlynn didn't take long to have her first orgasm. Her hips shook and her body quivered as she was cumming. "Oh, my God," she cried out.

I moaned out, "Finger me," as I shifted my lower half towards her body. I felt Kaitlynn's hand slide up between my legs and felt two of her fingers slide into me. My head was still facing down in-between her legs as she finger fucked me to a second orgasm while I continued eating her out.

After I came again, I pulled my mouth from her pussy and asked, "Are you ready for more?"

"Yes", she replied erotically with that little smirky smile she had.

I slid off the bed and walked over to my armoire. From and inside drawer I retired my "black panty style; skin colored 7-inch strap on". Kaitlynn's face turned blush red as I smiled at her showing her what was coming. I slipped into the panty style device with the attached dildo facing forward, like a big hard on. I walked over to my night table and grabbed the lube from my drawer. I climbed back on the bed, only to have Kaitlynn close her legs in embarrassment, fear and concern.

I whispered out, "It's ok, I know it's weird at first, but I promise you'll love it."

I slid back down in-between Kaitlynn's legs, lying flat on my chest. I started slowly and softly rubbing her pussy and clit getting her turned on again. I leaned in further placing my lips, mouth and tongue on her pussy. When I looked up, Kaitlynn's head was back, her mouth wide open and little soft moans were emanating from her. I watched as her hands cupped her breast as her fingers pulled on her own nipples. I got her to the brink of orgasm and got onto my knees. My hand still softly caressing up and down her pussy, I popped open the bottle of lube and poured a generous amount onto my hand. I grabbed the fake dick attached to me and stroked it like a man would be stroking his cock. Kaitlynn watched in anticipation and a sense of fear. I used a bit of lube and slid my hand up and down her pussy, getting her opening wetter and started getting on top of her. Kaitlynn's legs were spread wide open and she had picked herself up and was resting her torso on her elbows, as I lined up the dick. I swiped it up and down her pussy and got in closer. I slowly pushed the tip in as I heard her gasp. I pushed in a bit further and started sliding my hips back and forth letting the tip of the fake dick slide in and out of her. I didn't push it in all the way, because I wanted her to feel more comfortable with it just penetrating her. Kaitlynn moaned in pleasure as I slid it slightly deeper and deeper with every push.

I leaned on top of Kaitlynn and we began kissing. As my motion continued, she laid back flat on the mattress on her back. I was on top of her sliding my hips back and forth driving that fake dick deeper and deeper into her. Kaitlynn was moaning in pleasure like I had never heard before as our bodies became one. Kaitlynn and I made love that night. We spent the better part of the time, engrossed in kissing and touching, moaning and groaning as I slid every inch of that dick deep inside her, fucking her with my fake dick. From what I knew this was "the biggest dick" she'd ever had, so I can only imagine the pleasure of being filled by 7inches of cock (fake or not) and by someone like me who knew how to fuck a woman with a strap on. Plus, I can only imagine guys her age that she slept prior were the proverbial three-minute man. So, I planned on fucking her until her pussy completely satisfied. Kaitlynn was in absolute pleasure and I was getting off on fucking her with the strap-on. I watched her every move, picked up the pace when I felt she as ready for it, and slowed down to a soft in and out when I knew she had cum. I lifted her legs up around my sides and just continued giving her the fucking she needed, orgasm after orgasm.

Kaitlynn and I laid in this position for the better part of ten minutes, as I rammed my fake dick in and out of her tight pussy. Her moans increasing every time I got her closer and closer orgasm. Our bodies lye chest to chest and face to face as she screamed out, "Sam, holy fuck Sam." Followed by her body thrusting and shaking as she came. I brought her to multiple orgasms, each one greater than the one before. Her body quivered, her loins ached and she moaned words, I've hadn't heard before, or since. I finally pulled that dick from her pussy. I so wanted to roll her onto her stomach and slide it right up her ass, but she had never shown an interest in anal, so I decided it was time for her to suck her juices off of that dick. I climbed forward practically sitting on her chest, putting the dildo in her mouth as I told her, "Suck on it baby."

I watched as her little mouth slide that dildo in and out swallowing down every drop of silky slippery lube and her pussy juices on that fake cock, gagging her on occasion with 7 inches of dick. When I believed the dildo was clean, I pulled it from her mouth, leaned down and kissed her deeply again.

When we broke from our kiss, I asked her, "How did you like it Katie?"

Her face lit up and a big smile came across her lips, "Sam, it was amazing."

I laid down next to Kaitlynn as she rested her head on my chest. Our bodies glistened with sweat as she and I caught our breaths, my fake dick still standing erect. My pussy drenched, my asshole tingling. Kaitlynn leaned her head upwards to me and whispered, "My pussy is wide open and tingling."

I smiled knowing it was me that brought her the first real good fucking she had ever received. We kissed deeply for a while and I asked Kaitlynn, "Would you like to try it on me?"

At first, I think she was a bit hesitant because she didn't answer, but she finally mouthed the words, "I don't know how to do it."

"It's easy," I replied.

I climbed off of the bed and slid the panty style strap on off. I told Kaitlynn get off the bed as I helped her to her feet. I helped her climb into the panty portion of the strap on with the dick sticking out. She was amazed at how it felt to be wearing "panties", but yet have a big dick poking out. I laid down on the bed as I watched her play with the dick. Kaitlynn was amazed at how it looked on her and how it felt to reach down and hold a dick in her hand. She was as giddy as a school girl. She laughed and giggled, shook her hips side to side, watching the fake cock, swing back and forth, then up and down. She grabbed the lube from the bed and poured a lot on her hand and started stoking the dick like it was her own. "Make me cum bitch," she giggled out. Finally, her little two minutes of fun was over and she looked me deep in the eyes as serious as she could and said, "I want to fuck your pussy with this." Holding out the dick as if it was her own. I smiled and said, "Then come fuck me baby."

Kaitlyn came over to the side of the bed I was on and placed the strap on at my face. I leaned forwards and down a bit and slid it into my mouth. Her face lit up as she watched me giving head to her fake cock. I sild it in and out of my mouth as my hand slid in-between my legs rubbing my pussy. I moaned in pleasure as if I was giving my boyfriend a blowjob all while making myself wet in anticipation of being fucked. I pulled the dick from my mouth and pulled Kaitlynn down on the bed. She laid flat down as I went back to sucking the strap on more. My head bobbed up and down, as my left hand rubbed her tits while my right hand was rubbing my pussy and asshole. When I was ready, I climbed up on top of her. I got into the correct position and slid that 7-inch toy deep into my wide open, soaking wet pussy. I rose up and down on it like I was riding a real cock. Kaitlynn's face was in shock and amazement as I moaned and groaned in pleasure as it penetrated me deep. I rode the fake cock like it was real, bounding up and down on it hard. I leaned down several times kissing Kaitlynn deeply as we made love.

I placed her hands on my hips, on my clit and upon my tits, making sure she touched every erotic zone as I rode her. I came to orgasm after orgasm just bounding up and down on this cock. I loved looking deeply into her eyes every time I came and then slowing my motion down while we embraced. After I came a few times I leaned forward and whispered in Kaitlynn's ear, "I need you to fuck me in the ass."

As I pulled back up and looked at her, her eyes were glistening with fear and surprise.

I looked at her and said, "Yes, you heard me correctly. I need you to fuck me in the ass."

Kaitlynn didn't have much time to hesitate, because as I was climbing off of her, I pulled her upwards from the mattress. I got onto my knees and spun around so my ass was facing her. Katlynn got up onto her knees and climbed in behind me. I grabbed the lube and poured some on my fingers and rubbed my asshole with it sliding my fingers inside myself as to get ready for 7 inches of cock. I told her, "Just slide it in me."

I felt her edge closer and with several misses and several height adjustments, I finally felt the strap dick start sliding into me. I moaned aloud as she pushed it in further.

"Oh My God" she cried out in amazement that this big fake cock was deep in my ass and she was the one doing it.

I told Kaitlynn, "Just thrust your hips back and forth, until it's all the way in."

With some weird first movements by her, coupled with my body thrusting backwards, we finally got it all the way in. Kaitlynn got the hang of it rather quickly and set forth a good motion as she was ramming that fake dick deep inside my ass. It had been so long since I had a cock in my ass, the feeling was overwhelming. I came almost instantly.

"Don't stop Katie, don't stop." I begged of her.

After a few more minutes, Kaitlynn really got the hang of her hips swaying backwards and forwards, sliding that cock deep inside me, bringing me pleasure. I moaned aloud, and couldn't get enough of her fucking me in the ass with this fake dick.

"Kaitlynn fuck me baby," I kept screaming out, as I felt her jamming it harder and harder into me.

"That's it baby, use that cock, fuck my ass." I cried aloud.

I screamed out loud in pleasure as Kaitlynn brought me to back-to-back anal orgasms. And I wanted more, but I knew she was overwhelmed with the strap on itself, plus the anal thing, so I pulled away, feeling that strap on exit my ass. I spun around and kissed her deeply as we knelt into each other.

"Holy Fuck, that was amazing." I whispered.

Kaitlynn still in shock and overwhelmed with anxiety was at a loss for words.

We both collapsed on the bed and just cuddled close to each other. She and her big strap on surely relieved me; as I know I relieved her.

Eventually Kaitlynn took off the strap on and we both jumped in a shower together to get the lube and stickiness off of us.

Just as we were falling asleep Kaitlynn asked me, "Samantha, do you think you'll spend the rest of your life with woman or a man?"

I thought about it for a minute replying, "Honestly honey, I don't know. But my guess would be a woman."

"How about you," I asked?"

Kaitlynn moaned out some unintelligible words and dozed off having reached new heights and new levels of sexual experiences together. As I laid there I thought about her question. I thought back about Jennifer, Ashley and Anna and how this whole Kaitlynn situation came to be. I knew in my heart it was Ashley I wanted to be with, but didn't even know where to begin, especially considering she was married. I dozed off with Ashley on my mind....

The next morning, I was awoken by Kaitlynn rubbing her pussy next to me. I watched for a while as she pleasured herself, then slipped under the covers and finished her off by eating her out bringing her to multiple orgasms. When I asked her, what made her so horny this morning? She replied, "I was reliving last night, with you eating my pussy out, then the feeling of that big cock in my pussy. Fucking you in the ass and making you cum hard. Samantha it scares me a bit to be this into you and lesbian sex, but last night was the best sex I ever had."

Kaitlynn and I spent just about two more weeks together before her and her mom headed back to St. Louis. I do miss her and I think about her a lot. We did stay in contact for a while, but we never saw each other again. At least up until now we haven't. I don't know what is going on in her life. I don't know if she is dating women or men, or both. All I know is when she left here, she was heading towards being full blown lesbian, just missing dick on occasion. Like I am.

A few days before she left, reality hit me. I knew Kaitlyn was leaving for good and I was going to be alone and I knew I needed a friend and a lover. I finally mustered up the courage and texted Ashley. We started talking again opening up a great new friendship and possible romantic connection.

Just a hint for future stories, Ashley and I did start a relationship, with her husband included (on occasion), which has been ongoing ever since.