GTO – The Beginning Pt. 05

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All characters are over 18 years old.

This story is about how Gail became the seductress she is. I really encourage you to read my first story “GTO” to understand fully who Gail is as I spent much more time on her background there. This story takes place at the beginning of summer between her Junior and Senior year of high school.

As you read this, please keep in mind that Gail is a very complicated person who is just learning about her sexuality. She is experiencing different aspects of sex for the first time. This is a story about a young adult finding herself and experiencing new pleasures in different forms. I got a little ambitious in my planning of these stories.

Order of stories in the GTO seriesGTO — Gail at 42-years old, Character introductionMature, Lesbian, FFM, Mild domination

GTO — The Beginning — PT. 01, Summer after turning 18 before her senior year of High SchoolLesbian, First time, masturbation, mild domination

GTO — The Beginning — PT. 02, Summer after turning 18 before her senior year of High SchoolLesbian, mild domination

GTO — The Beginning — PT. 03, Summer after turning 18 before her senior year of High SchoolLesbian, first time, no domination, just Gail learning the joys of sex with another woman.

GTO — The Beginning — PT. 04, Summer after turning 18 before her senior year of High SchoolLesbian Domination

GTO — The Beginning — PT. 05, Summer after turning 18 before her senior year of High SchoolFirst time experiencing sex with a man.

GTO — Queen of the Dragstrip — Middle of summer in Boston before starting her senior year of high school.Lesbian, Non-graphic hetro and a little mild BDSM thrown in at the end.

GTO — The Beginning — PT. 07, Back at school for her senior yearComing soon
Not sure how this one will play out yet. This may get extended.

GTO — Office DisciplineGail at 42-years old.
Gail deals with a male employee accused of sexual harassment.
Femdom with a little mutual lesbian thrown in.
Takes place after GTO
Includes a couple of old friends.

GTO — NieceGail at 42-years old.
Gail’s Niece discovers her secret.
Lesbian sex with a little domination
First time with a girl for Gail’s niece.

As always, comments are always welcome, but if you don’t like something, at least tell me what the problem is. Those “If it doesn’t get better, you will lose a reader!” comments don’t really help. If you don’t tell me what you don’t like, I really can’t fix it. I’m not a mind reader.


“You are really taking to your training well, Gail. I’m very impressed with how well you’re doing.” Aunt Elizabeth said at breakfast Friday morning.

“Well Auntie, I told you that I would give it my all, and you know how dedicated I am when I go all in on something.” I smiled. “Plus, I really hate to lose at anything, so I strive to be the best at anything I put my mind to.”

“Yes, there is that. As well as the natural grace, confidence, and nasty dominant streak in you.” She laughed.

“Besides,” I grinned, “you are kind of a bitch, so I decided to be a bigger bitch than you.”

Auntie kind of glared at me on that one. “Don’t go getting cocky. You have a long way to go before you match me in being a bitch.”

I cupped my tits and laughed, “I respectfully disagree. Being ‘cocky’ will not be an issue with me.”

“Touché'” she saluted with her coffee cup.

“Speaking of ‘cocky’,” Aunt Elizabeth went on. “How do you feel about men?”

“As you are aware, I have never felt one before, so I can’t really answer that question.” I had a feeling that this was going to come up at some point. I just wasn’t sure what I thought of it. I was a complete virgin when I came to Boston to stay with my aunt for the summer. I had never even masturbated before. I was so into working on and driving fast cars that I never even gave sex a thought. Sure, I knew that some guys were attractive, but I just never thought about it. I was a loner and relationships didn’t interest me. Same thing with girls. The thought of sex with a girl never entered my mind until I happened to accidently catch Auntie with her PA right after I arrived. Since then, Aunt Elizabeth had introduced me to the pleasure of lesbian sex (not herself, although she is a beautiful woman, but with her a couple of her friends and their submissives). I had been a blank canvas for her so far, so it didn’t come as a shock that she would eventually bring up men. In fact Auntie had taken me to her gynecologist my second day here and gotten me on birth control, so I was prepared for this eventuality.

“Well, does the sight of them repulse you?” she asked.

“No. I mean I can tell if a guy is attractive, but I just haven’t thought of it in that way.” I replied.

“Hmmmm, perhaps it is time to find out then. You should at least try it. Then you can decide if you like it or not.” She insisted.

“OK. Trying new things has so far worked out this summer.” I agreed.

“Indeed, it has.” She laughed.

We chatted about other stuff as we finished breakfast. Finally getting up, Auntie informed me, “You should get ready for the day. I have to go to the office today, but Jenn bilecik escort will be back after she drops me off. We are having a cocktail party here tonight with some of my friends and people from the office. I would like you to help Jenn get things ready. The party will start at around 9:00 tonight. You might want to hit the spa this afternoon. Cocktail parties are where you really need to ‘glam it up’.”

I’m not going to bore you with the details of the day. Jenn and I spent the morning getting some supplies and preparing the house. Auntie had a maid service come in and detail the house. Jenn took me to the spa where we both got the works in the afternoon. Manicure, pedicure, hair, makeup, and waxing. The landscapers came and prepared the yard while we were out. The pool guy had done the pool and hot tub a couple of days ago, so that was already taken care of. There wasn’t going to be any swimming anyway, but it did need to look pretty.

“Gail,” Aunt Elizabeth began over an early light dinner. “There will be several unattached men at this party tonight. I would like you to at least look them over to see if there is any attraction for you. I am not going to force this on you, but I think that you should at least consider it. If you do, feel free to DISCRETELY adjourn to your room.”

“Are you suggesting that I might rip off my clothes and start an orgy in the middle of the living room?” I asked sarcastically.

Smiling, she looked me in the eye, “I have no doubt that if you took off your clothes and offered yourself in the middle of the party, that it would indeed devolve into a full-on orgy. Unfortunately, this is not that type of party.”

The caterers and bartenders arrived at 8:00 to begin setting up, and I went upstairs to change. I decided on a slinky red cocktail dress with matching 5″ heels and mocha stockings and garters. The dress was too low cut for a bra, but I did don a lacy red thong. I had to admit, I looked GOOD!

The guests had all arrived, and the party was going full swing. It was actually very pleasant. People mingling, drinking casually, and munching on hors d’oeuvres.

Auntie had been introducing me to everyone as they arrived. There were several younger guys that I found rather attractive, but none that really wowed me. There were also more than a few women that I found attractive as well. Of course, the guys showed more than a passing interest, but even a few of the women eyed me appreciatively. Linda was a new attorney that had just passed the bar exam. She was young, single, and gorgeous. She also was casually eyeing me as I was mingling. Hmmmm, maybe it’s time to start looking at a fallback option.

I excused myself from the conversation I was having with one of the law firm’s partners and his wife, so I could get another glass of wine. I was mildly flirting with the bartender as she was pouring my wine when someone moved beside me.

Turning, I looked straight into the blue eyes of the blonde goddess named Linda. She was approximately 5′ 4″ tall, willowy with perhaps C cup breasts. Very beautiful.

“Hello. Are you enjoying the party, Linda?” I asked.

“Oh yes. You’re Elizabeth’s niece Gail, right?” I nodded. “Sorry, I just started at the Firm, and it’s taking a bit to get to know everyone.”

“That’s fine. I know how you feel. This is the first time I’ve met most of the people here too. So, I understand congratulations are in order for passing the Bar Exam. Intelligence and beauty. You must really have all the guys flocking to your door.” Over the top? Perhaps, but the sly smile and beginning of a blush told me it was right on.

“Well, truthfully, I’ve been a little busy to date lately. In fact, this is the first time I’ve had a chance to socialize for about 3 months.”

We had gotten our drinks by then and I maneuvered her outside to a quiet corner of the patio. We spent the next half hour chatting about our backgrounds. I noticed more than a couple quick glances at my legs and chest. She was showing definite signs of interest there.

“Oh, Gail. There you are.”

Turning, I found Aunt Elizabeth walking towards me with a Greek God in tow.

“Gail, I wanted to introduce you to Andrew. Andrew, this is my niece Gail. She is staying with me for the summer.”

OK. This was definitely interesting.

“Hello, Andrew. It is a pleasure to meet you.” YOWZA!

“Hi Gail. Sorry for my stare, but I must say that your Aunt did not prepare me properly for how stunning you are.” Cheesy? Yep. Effective? Well, yeah.

“Thank you, kind sir. I must say that you look quite dashing yourself.”

Hmmm, a rather wicked idea just flashed in my mind. Now, how to go about it.

“Oh, pardon my manors. I see that you two lovely ladies need your drinks refreshed. As your aunt absconded with me as I was just headed to the bar, perhaps I could get you two a refill as well?” Andrew offered.

“Wine is it then? I shall return shortly.” He said as he turned towards the bar.

“Linda, do you mind if I borrow Gail for a moment? I have something quick to discuss with her.” Auntie said reaching for my hand.

“Well, as a Plan B, Linda is a worthy manisa escort subject.” Auntie said when we got to a quiet spot.

“Yeah. Sorry Auntie. I really did try, but none of the guys really did anything for me, that is, until Andrew showed up.” I replied. “Now, I’m kind of wondering about a Plan C.”

“Oh? Do tell.” Auntie said with raised eyebrows.

“Well, it is obvious that Andrew likes girls. I’m also getting the distinct vibe that Linda probably also is at least interested in me. The question is whether Linda would be interested in both Andrew and me together.”

“And what makes you just assume that Andrew would go along with that as well?”

I gave Aunt Elizabeth my ‘Are you kidding me’ look. “He is a guy, right? Have you ever heard of a strait man that didn’t have a two-girl fantasy?”

“Good point.” She relented. “Then this should be a good test for you. Hmmm, Linda and Andrew at the same time. If you manage to pull that off, I’m going to be very jealous of you. Good Luck.”

There was an older, rather pudgy and balding guy sitting next to Linda when I returned. The look she gave me as I walked up told me that she was not interested in his feeble attempts to get to know her. Time for a rather bold play. I wasn’t overly worried. I had a back-up play in case it didn’t work like I thought.

“Sorry it took so long, baby, it seems the bathroom is rather popular.” I said as I leaned in and gave her a quick kiss on the lips.

To say that she wasn’t expecting that would be an understatement. Her eyes went as big as dinner plates as I moved my head back and looked into her eyes. With a smirk on my lips, I winked with the eye opposite of where the guy was sitting. It took her a second to comprehend what I was doing, but she immediately got into the act once she figured it out.

“No problem Sweetie. You weren’t gone that long.” She reached for my hand and held it as I maneuvered into the chair next to her and scooted it closer.

“Have you met my girlfriend Gail? Gail, this is Jim He is a researcher at the Firm.”

“Very nice to meet you Jim.” I said. Looking back at Gail, “Sorry Baby, there was kind of a line at the bar, so I didn’t get us more wine. Although, knowing what happens to your inhibitions after a glass to many, maybe that is a good thing. Wouldn’t want to wake up with a strange guy in our bed again.”

“Yeah. Sorry about that. I just needed a reminder why I changed to the other team.” Linda smirked. Then her smile evolved into an evil grin. “Too bad he ran out of the house when you opened the toy box and started to pull out the whips and floggers.”

Oh, this girl was fun.

“Uuuuuummm, pardon me ladies. I see Ms. O’Malley over there. I really need to speak with her for a minute.” Jim stammered as he practically ran away.

“Oh, you’re bad.” I said smiling.

“Yeah. Well, he is totally not my type.” She grinned.

Deciding it was time to make a subtle move, I leaned in and whispered, “So, what is your type?”

Staring straight into my eyes, she asked, “That depends. Do you mean guys or girls? Ever done a threesome before?”

OK then. Apparently, I was the one about to get seduced. That works.

Noticing out of the corner of my eye that Andrew was on his way back with the drinks, I replied, “Only with girls. I’ve never been with a man before, but I want to try it.”

Without even breaking our eye lock, she said, “Andrew, tonight is your lucky night. It seems that Gail here just can’t seem to decide whether she want to take you or me to her room right now. I was about to suggest that she didn’t need to decide between us, and we all adjourn upstairs together. Do you think you are ‘up’ for it? Oh, and as an added bonus, you get to be her first real cock.”

Andrew somehow managed not to drop the glasses he was carrying.

I winked at Aunt Elizabeth as she saluted me with her wine glass while the three of us headed for the stairs.

I pulled Linda into a passionate kiss as soon as we entered our room. Andrew had followed us in and closed the door.

“She hasn’t been with a guy before, Andrew, so why don’t you sit back for a bit and enjoy the show as we get warmed up.” Linda said after we broke the kiss.

OK. I didn’t really mind her taking charge a little bit, but I decided to show that I wasn’t at all submissive. Even though it was hidden, I was actually pretty strong. I moved my hands to her ass, grabbed hold, and lifted her off her feet. Moving to the bed, I tossed her down and jumped on top of her. Her eyes went wide in surprise as I grabbed the back of her head and aggressively kissed her again. While my tongue was exploring her mouth, my right hand had moved to her thigh and was slowly exploring upwards. She moaned into my mouth as my fingers made their way to the gusset of her thong. I smiled as I felt how soaked it was.

I broke the kiss and looked over at Andrew. He had already discarded his clothes and was stroking his cock. I estimated it to be about 8-inches long. Not too thick, but far from thin. “Nice.” I said when I finally moved my eyes from his groin to his face. “Just make sure that the first load mersin escort goes inside me.” I warned as I continued to stroke Linda’s pussy through her thong.

Looking back at Linda, I decided to start moving things along. “You know, baby, this dress you’re wearing would look a lot better pooed on the floor at the foot of my bed.” I explained.

“Hmmm, I think you’re right. And yours would look fantastic right beside it.” She grinned.

I let her up, and we shucked our clothes. She was right. They did look better pooled next to each other. I moved over behind her as she was reaching for one of the garter clips holding her stockings up. Reaching around and fondling her breast, I whispered in her ear, Leave those and your heels on Darlin’. I love the way you look in them.”

With her hands on top of my hands fondling her breasts, I turned us so we were facing Andrew. “I think someone is getting a bit lonely. Do you think we should bring another player into the mix?” I asked.

He didn’t need to be officially asked. He bolted out of the chair and was wrapping his arms around us cupping my ass before I even finished the question. As he locked his mouth to Linda’s right breast, I moved my displaced hand down and began stroking his shaft. It was a lot different than the strap-on and dildos I was used too. It was both hard, yet velvety soft. I could also feel it throbbing, which a fack cock could not do. I felt a new wave of fluid gush from my pussy at that. So, perhaps I’m not a complete lesbian after all. I slowly started to move back while pulling Linda and Andrew with me as I continued to nibble and kiss Linda’s neck.

“I think she’s ready for you.” Linda whispered to Andrew.

We disentangled. Linda moved to the bed and sat with her back against the headboard as Andrew put his arms around me. “Are you ready Princess?” he said as he lowered his lips to mine. His kiss was different than those of a woman. It was rougher and more aggressive. I can’t say that I liked it any more or less, but it was different. Yep, I would be doing this again.

“Fuck me Andrew” I moaned when he broke the kiss.

“In time, Princess.” He whispered. “But first, I want to taste you.”

Andrew and Linda maneuvered me onto the bed onto my back, so my head was laying in Linda’s lap. Linda reached down and began fondling my breasts as Andrew climbed onto the bed with his head between my spread legs.

I have to say, he knew what he was doing. Yeah, I had overheard the girls at school talk about the fumbled attempts that guys made in licking them, at least those guy that were willing. Even the few girls that had so called ‘sophisticated’ college boyfriends complained about the lack of prowess that guys had with eating out a girl’s pussy. There were a few quiet whispers from the more ‘adventurous’ girls stating that only another girl could properly lick another girl’s pussy. True, he was no Cassandra, Bethany, or Jenn, but he sure did seem to know his way around down there. He took his time exploring with his tongue. He had wrapped one arm around my leg and used his finger to draw lazy circles around my clit. At one point, he stuck his tongue as far inside my tunnel and then began to wiggle it around. I’m sure that everyone still at the party heard my shriek when he did that. Between what he was doing with his tongue and Linda working over my tits, I was going mad. Soon, I couldn’t take it anymore. I grabbed the back of his head, pulled him in tight, and locked my legs around him. I think he got the message, because he started concentrating his tongue on my clit. At the same time, Linda began to pinch, twist, and pull my nipples. I started moaning louder, and louder, and louder. My eyes rolled up into the sockets. I saw red. That flashed to yellow. When the yellow flashed to green — LAUNCH! I heard myself cry out in release as the orgasm came over me.


I was relishing the exquisite taste of this ravishing young woman that I had just met. Damn, she tasted sweet. I had been lucky enough to have been taught how to properly please a woman by an older neighbor of mine right after I turned 18. She seduced me the weekend after my birthday, then spent every moment we could get together before I went away to college teaching me the art of making a woman cum multiple times. As with everything else I did, I was an exceptional student. Elizabeth had grabbed me as soon as I arrived (late) to her party. She told me that she had to introduce me to her niece, and that she thought that we may hit it off. I had to admit, I was a little disappointed at the way she was acting with Linda when Elizabeth took me over to introduce me, but Elizabeth prodded me to take a chance. I didn’t know what to think about Linda. She had joined the firm recently, and I knew that she wasn’t dating anyone. I had made a couple of subtle moves on her, but she hadn’t shown the slightest interest. Seeing the gorgeous creature being introduced as Gail, I almost lost all control. OH! MY! GOD! How is it possible that a woman this beautiful isn’t being surrounded by a plethora of suitors? I mean, Linda is very stunning, but sitting beside perfection……. I have no recollection of the next several moments. Suddenly I was making my way back to this goddess with three drinks in my hand. My heart fell as I saw her and Linda in a very intimate exchange. I was sure that all hope was lost, and that Linda would be occupying her bed tonight. As I got to the table, I almost came in my pants when I heard what Linda had said to me.

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