Samantha's First Experience Pt. 07

Samantha Pt 7

Please go read part 1 through 6 before reading this...

After my surprising make out session with Ashley, I decided it was time for me to completely put Jennifer behind me and just date whomever I find and want to be with. I got back into working out and noticed a guy at the gym who I crossed paths with a few days a week. He was cute and wasn't there to be a show off or flirting with everyone, he was just there to better himself. One day we were both heading to the same machine and he gestured for me to go first. I thanked him and introduced myself. He introduced himself as Bobby. Bobby was about 5'10, medium build, with a bit of a pot belly (that I thought was cute) he had short brown hair and seemed like a normal guy. I wasn't quite sure of my feelings for him, but I liked talking to him and found myself more and more interested as we become friends. Plus, I needed some dick.

Bobby finally asked me out and we went for a bite one night after the gym. Over the next few weeks, we started talking, texting and hanging out more and I truly enjoyed getting to know him. We started dating exclusively in late October and began our relationship. It was weird at first being with a man again, but just like riding a bicycle again, I started riding Bobby. LOL. He was so nice and kind and made love to me like a woman should be made love to. We were working on building a great relationship and things were progressing as they should have. I was happy being with him and being back in a more normal situation. Almost two years later when I returned to work for the fall school year I found out I had to go to Nashville for a week-long training class on curriculum development. The classes were slated for in late October, a month before thanksgiving break and would be attended by teachers and administrators from around the U.S. According to the curriculum there were daily training modules and every person would attend all the modules throughout the week. The school booked me and three other new teachers into hotel rooms, each having their own and paid for everything including the travel costs. I was nervous to go, but excited.

Bobby and I celebrated our two-year anniversary just before I left and I hoped he could have gotten some time off of work to go with me, but unfortunately, he couldn't go. So, I ended up heading to Nashville by myself. I left my house early Sunday morning taking the 12-hour drive to Nashville. I arrived later in the evening, checked in, found out what rooms my co-workers were at in the hotel, had a bite and went to sleep.

Monday...And the start of my third lesbian experience.

My first day of class I sat next to a female Filipina Assistant Principle from suburban Indianapolis, her name was Anna. In conversations I learned she was here to add on to her credentials for a Principles job. She was very sweet, had medium length brown hair, brown eyes, a soft rounded Asian face, with sexy voluptuous lips, a medium sized build with normal to bigger sized tits and a great big smile. Anna was 45 and had been teaching for more than twenty years, with a recent promotion to AP. As the day progressed, we chatted more and got to know each other a bit. Turns out she was divorced and getting over a man she had fallen for a while ago and was just here to get away from the woes of back home. After the first round of classes ended, I headed to lunch and when I arrived at my afternoon training module, I saw Anna again. I went to sit by her because I knew no one else in the room and the other teachers from my school were in other modules. We worked in groups throughout the afternoon sessions and by the time the day was done we were all mentally spent. I went back to my room that night and just hung out with my other teachers from work.

I didn't see Anna on Tuesday, or Wednesday morning, but I did see her sitting in the hotel café at lunch time on Wednesday afternoon, so I asked her if I could sit with her. She seemed happy to run into me again and we spent the entire lunch hour talking about the classes and educators who were teaching. When it was time to go back, Anna asked me, "What classes I had and what time I was done?"

Unfortunately, we would not have any modules together today, but I told her maybe I'd see her later tonight because some of the teachers where going to the pool area to blow off steam after dinner. I had told Bobby along time ago about my lesbian experiences and he told me that he had been involved with some Transgendered women before and was "somewhat Bi-Sexual". On Wednesday afternoon when I talked to him on the phone, I guess I had mentioned Anna one to many times, because he asked me about her; implying she was all I could talk about. I did admit to him that I found her very beautiful, interesting and I was curious about her, but didn't want to do anything behind his back. Bobby said, "If something happens, I'm okay with it as long you tell me about it and I get some pictures. LOL."

Wednesday night pool party --

A lot of the teachers had come down to the pool area, there was a hustle and bustle throughout the room. People sitting around the pool deck and at tables drinking wine and conversing. I was sitting back with my co-workers enjoying a well-deserved glass of wine, when I saw Anna walk into the room. She was wearing this sexy white two-piece bikini over her light brown skin. Her body looked incredible. I was in awe. I hadn't even looked at another woman sexually since Jennifer, but I tell you the way she looked was stunning. Anna saw me sitting at the table, smiled and waved hi.

My co-workers asked who that was? I explained she was one of the AP's I had been working with the last few days. Anna came over and sat with us. I introduced her to everyone. After a bit of talk, I wanted to swim and so did Anna, so we excused ourselves and climbed into the pool. During our time in the pool, we started flirting with each other. We were trying to not be obvious with all these people around, but it was hard to hide. We spent time pulling each other through the water, throwing pools toys at each other, using the pool noodles to poke and prod each other and at one-point Anna even pulled the strings of my bikini top open. I was so enamored by her. I had feelings in my stomach that I hadn't had since my first few times with Jennifer. And even though I was with Bobby, I was absolutely attracted to her, and wanted to fuck her. But, did not know if she was Bi-sexual or even Bi-curious.

As the night progressed the pool area started to quiet down and people started to leave. Anna and I were sitting in the hot tub. We were sipping wine, laughing and enjoying each other's company. The last of my co-workers got up to leave and she gave me a dirty look -- as if she knew Anna and I were interested in each other -- almost angry that I was spending time with Anna and not her. Once everyone I knew was gone from the pool, I decided to make my move. As we sat, I placed my hand on top of Anna's hand and began rubbing over it. She looked at me and smiled. Over the next few minutes, our fingers swirled and twirled in and out of each other's fingers and rubbed around our wrist areas. I moved closer to Anna and whispered in her ear, "I am so glad I met you here."

Anna replied, "I am too."

I placed my hand on her leg and was slowly stroking up and down her leg. Anna didn't seem to mind and shyly smiled at me. We sat quietly staring into each other's eyes as I felt butterflies in my stomach. Every time someone walked by, we acted as if we were just chilling out and nothing was going on, but I think we both knew we were getting turned on for each other. I wondered if Anna had any experience with women, because I know she was married. Maybe she is Bi. Maybe just curious, maybe just drunk, either way I haven't had these feelings for a woman since Jennifer and I'd really like to kiss her right now. We sat a bit longer and Anna's hand was on top of mine as I rubbed up and down her leg. She opened her legs and pressed her left leg up against mine. I felt her guide my hand deeper between her thighs, but I never pushed my hand all the way up to her pussy, although I did slide up a bit further than I should have on occasion.

As her hand guided mine up and down and in-between her thighs a million thoughts ran through my mind. Did she want me? Was she just being a flirt? Should I move further up and touch her? We kept our conversation going as if nothing "out of the ordinary" was going on. I was confused on what I should do. We smiled at each other a lot, starred into each other's eyes, but neither of us made a distinct move. Maybe because people were still here at the pool, maybe she was scared to, maybe she wanted to, but wasn't sure if I was interested. Either way we both sat there and neither of us made a move. As the night was winding down, I knew I had an early start tomorrow and as much as I want to stay here with her, I said, "It's getting late, I think it's time for me to head back to my room."

Anna replied, "Yeah, I was just thinking the same thing."

As we climbed out of the pool, we grabbed some complimentary robes and Anna said, "I'll ride up the elevator with you."

I was staying on the 7^th floor and Anna was on floor 8. As we walked to the elevator, I felt like something had changed between us. Maybe nervousness had set it, maybe concern, maybe reality, but the flirting wasn't there and I almost felt disappointed that we hadn't kissed in the hot tub. As we rode up the elevator, the silence was deafening and the tension between us could be cut with a knife. When the doors opened on my floor, I said, "Well Anna, it has been a great night, I hope you sleep well and I get to see you tomorrow."

Anna replied, "I hope so too."

Just as I started to step out of the elevator, I felt Anna's hand reach out and softly grab my hand. I stopped my forward moment and turned back to her.

Anna nervously blurted out, "Wait! I was hoping we could spend some more time together."

"What do you in mind? I asked.

Anna said, "Well, maybe we could have more wine in your room, or mine."

My heart skipped a beat and without hesitation, I moved forward to her and placed a big deep closed lip kiss on her lips. My stomach was doing flips. After realizing what I just did I thought to myself, should I have done that? Did I take her wanting to spend time together wrong? As I pulled away, I said, "Anna, I'm sorry I shouldn't have done that."

I could see Anna was taken-a-back, but excited I had made a move.

Anna mouthed out, "No it's okay."

We stood silent for what seemed like an eternity just starring into each other's eyes. Anna moved in closer to me and leaned in for another kiss. This time our lips parted, our tongues touched and swirled around our mouths. My heart was racing and I was shaking like a leaf on a tree. As we stood kissing the elevator doors started to close. I reached back and extended my arm out to stop the door as we stood embraced in a deep kiss. Anna's kiss was incredibly, so soft, so warm, so wet. Her big Asian lips just caressed mine as our tongues danced in each other's mouths. We hadn't broken from our kiss when the doors of the elevator started to close again. This time I pulled from our kiss, looked Anna in the eyes and I pulled her out of the elevator.

I guided her down the hallway by her hand to my room. Neither of us said a word as we walked, but my stomach was doing flip flops. I was nervous and I wasn't sure if we were going to have sex, or just spend time together, but either way I was excited she was coming along without hesitation. After getting into my room, Anna and I stopped and had another deep passionate kiss. We were both wearing the robes from the pool with only our bikini's on under. Anna pulled from our kiss and said to me, "It has been a long time since I have been with a woman, I may be a little rusty."

My heart jumped. She did want me! She knew, as I did, that we both wanted each other and we were going to have sex.

I smiled and said, "It's been a couple of years for me too. So, we'll take it slow."

I kissed Anna again with passion. This time there was no fear, or concerns of misgivings. We were here alone in my hotel room in Nashville about to have sex and I was so excited about it. I wanted to make her feel special and comfortable with me. My pussy was tinging and getting wet. I hadn't wanted a woman like this since Jennifer and I don't know why I was so attracted to her, but I wanted her badly. I reached down and untied her robe letting it fall open. Anna's hand ran up the side of my face and under the back of my hair along the back of my neck. She sent chills down my spine. I wrapped my arms around her under her robe, feeling her soft skin in my arms. I felt Anna pull at my robe strings. I helped her untie it and dropped it to the ground. We pulled closer to each other, our Bikinis touching, still partially wet from the pool making us cold.

I walked Anna over to my bed. I pulled the bedding back and we both climbed onto the bed pulling the cover over us. We laid side to side kissing and petting each other. Anna had plump round low hanging tits, that age and gravity affected, but I didn't care. I reached under her bikini to feel her breasts. It was amazing feeling her soft skin and having a tit in my hand again while kissing a beautiful sexy woman. I felt her reaching behind me un-tying my bikini top. I assisted her in taking it off. I pulled myself up over her face and placed my breast in her mouth. Her mouth covered my nipple and her warm wet tongue was swirling around sending intense feelings rushing through me. My hand pulled her bikini top up exposing her breasts. After she sucked on my nipples for a while, I inched back down and placed my mouth on her right tit. I sucked it with passion, I listened to Anna moan as I explored her sexy tit. She was trying to untie her bikini top, eventually giving up and just ripping it over her head as we both let out a giggle.

We went back to kissing each other as our bodies pulled closer, my breasts touching hers. I felt her leg lift up and rest over mine. Our heads going back and forth from side to side as our tongues worked on getting each other turned on. I slid my hand in-between her thigh just under her elevated leg. My hand rubbed back and forth and up and down her leg feeling her body respond. Finally, I made it all the way up to her bikini bottom. I cupped her pussy as Anna let out a moan. I rubbed up and down her pussy over her bikini making her hotter and wetter and getting myself even more turned on. I pulled at the strings of her bottom opening it up. I slid my hands down into her bottom and felt her pussy. She had a bit of hair, but it was short and felt sexy. As we kissed, I kept rubbing up and down her, feeling her hips moving back and forth and her moans increasing. I used my finger and started rubbing her clit, getting her more turned.

I rubbed her clit until I knew she was wet enough and ready enough for my fingers. I slid a finger into her and Anna pulled from our kiss. She leaned her head back and let out a deep long sexy moan. I kissed her neck as my finger was sliding in and out of her. When Anna's head came back forward, she grabbed the back of my hair, looked deep in my eyes and said, "Finger fuck me."

I about exploded. Even Jennifer never said that to me. Anna didn't go back to kissing me, she just kept immense eye contact with me moaning louder and louder as my finger was slamming in and out of her. Anna was thrusting her hips forwards and backwards assisting with bringing herself to orgasm. Within a minute Anna was screaming, "I'm going to cum!"

I pushed my finger in and out of her as fast as I could. Finally, with a loud groan and a light following scream, I felt her body start quivering and her legs start shaking. She was cumming all over my fingers. "OMG" Anna cried.

I got her off. The smile on my face was a wide as can be. Anna pushed me onto my back, got up on her knees, flipping the covers off in one fall swoop. Anna grabbed at my bikini bottom and pulled it down. My heart was pounding, I was breathless, I was so turned on. I was already soaking wet from flirting all night, making out with her and now fingering her to orgasm. Anna spread my legs and said to me, "What a hot sexy pussy."

I can only imagine how bright red I was. Anna slid down in-between my legs and within seconds her mouth was all over my clit. I felt the tip of her tongue swirling around it. Flicking at it, teasing it, making me want her to dive into it further. I pulled my knees up so my feet could rest on the bed, spreading my legs further apart. Anna licked my pussy like a pro. Her tongue ran up and down my lips, her fingers caressing me. I heard loud slurping sounds and was so ready to cum already. Anna licked me to the point of exploding. Just as I was about to cum, she slid two fingers deep inside me and she began thrusting them in and out of me looking up and staring at my face, making deep eye contact. I moaned louder and louder begging her not to stop. I exploded all over her fingers, as she kept ramming them deep inside me. She left her fingers deep inside me, as she softly continued teasing my clit with her tongue, kissing up and down my thighs and letting me slowly come down from my orgasm.

As Anna looked up at me again, I erotically blurted out, "I want to taste your pussy."

Anna smiled, adjusted herself back onto her knees, swung around, climbed over me and slowly backed herself up to my face. She placed her hot wet Asian pussy right at my mouth. My head motioned upwards as I began licking up and down her hot sexy pussy. Her lips were full and plump and she was dripping wet and wide open. Before I could even really start eating her out, Anna's face dipped right back in-between my legs and I felt her warm tongue just licking up and down my soaking wet lips. We spent the better part of twenty minutes just eating each other out. Her pussy tasted amazing, we both orgasmed at least three times more, using our tongues, mouths and fingers. After we both orgasmed and were drained, Anna climbed off of me and swung around again.

We kissed deeply tasting each other's pussies and cum. She pulled the blanket back over us as she laid down next to me. I said to her, "That was amazing, I thought you were going to be rusty?"

Anna replied, "I thought I would be, but I wanted you so bad, it all came back to me really quickly."

Anna and I sat talking about our previous lesbian experiences. She admitted the first day she saw me, she had an instant infatuation and was so glad that I had come sit next to her, sat with her at lunch and had this night with her. I also admitted my attraction to her, especially tonight when we spent time in the pool. I was in amazement. I figured this trip was going to suck. I had never expected to meet someone here that I would get along with, let alone find a beautiful sexy woman I ended up having hot sex with.

Just as my pleasures and enjoyment of her were coming down I realized I owed Bobby some picture. I explained to Anna, I had a boyfriend back home and he said I could have sex with you, but he wanted pictures. Rather embarrassed and concerned about someone seeing her face, Anna agreed to a few select shots. We took a few just laying naked together from the neck down, I took a few of her pussy and she took some of mime. I sent them off to Bobby. He didn't reply that night because of the time change, but I am sure he awoke to quite a surprise.

I apologized to Anna for asking, but I said, "If pictures are what I have to do to be with you. I'd take all he wants." She giggled.

I asked Anna to spend the night with me, she smiled and said "Yes".

After getting ready for bed and shutting the lights off, we climbed back into bed cuddled in each other's arms until we fell asleep, naked, warm, exhausted and sexually fulfilled.