When I graduated college I wasn't naïve or a virgin, but I was definitely inexperienced. I had only two sexual experiences. My first was with a boy I was seeing in my junior year, and the second was a one-night stand during graduation week.
Like I said I wasn't naïve, I had plenty of girlfriends with plenty of drama. The problem was that I was shy and conservative, and I attended few parties in college.
My parents were very strict. School and good grades were their biggest priority. Boys and dating were an unnecessary distraction.
All of my hard work paid off after graduation. I was able to get a teaching job at a nearby middle school in September. When most of my friends were still applying for jobs, or signing on for substitute positions, I was setting up my classroom and writing lesson plans.
I met many new friends at my new school, but there were two male teachers who are the primary characters in this story. First was Frank. I met him first and we became immediate friends.
He had a doctorate and was the head of the English department. He was also a published writer. I soon grew to respect and admire him. Even though he was nearly twenty years my senior, we soon started dating. I adored him.
He was nearly forty and not a striking figure, but his quiet demeanor and class won me over. He was actually a very good dresser. Remember, I was only twenty-two and easily impressed by an educated man.
Frank and I became intimate very early in our relationship, maybe too early. I had too much to drink on our second date and we ended up in bed. He had an incredible influence over me, even from the start of our relationship.
I have to admit that he was the one who brought me out of my shell and introduced me to a whole new world. I was always conservative and shy in my actions and dress. Frank helped me to break out.
It started with people. As soon as we started dating he brought me around to all of his friends. We started to frequent quite a few nightspots and restaurants. Although most of his friends were academic people, they were all very nice and quite the partiers.
I soon became conscious of my dress. All of the other women were wearing tight jeans and heels while I wore my usual conservative outfits. They dressed like the pretty girls that I admired, but never had the nerve to emulate.
"Frank, do you like the way I dress?" I asked him one Saturday night while we stood at the bar of a restaurant where we had just had dinner.
He knew that he was treading on shaky ground. "You are a beautiful woman."
"That's not what I asked you. Do you like the way I dress?"
"I don't dislike it," he avoided the issue.
"But you don't particularly like it?"
"Well, you are so beautiful, and you have such a wonderful figure, maybe you should show it off a little more." He cringed expecting me to be hurt or mad. But I knew he was right, and I wanted to dress like some of the other woman, but I didn't know how.
"I know, but I'm at a loss when it comes to fashion. I haven't got a clue."
"I could help."
"Well I'm not a girl, but I see what the young girls in school are wearing, and I know what I like. We could go shopping together tomorrow?"
"Really? You would do that for me?"
"Actually I would love to see you in some sexy clothes."
"I don't have much money."
"If you wear what I pick out, I'll buy it. If you really think about it, it would be a present for me."
"Okay." I shouldn't have been accepting gifts from him so early in our relationship, but what young girl would turn down free clothes. "What did you have in mind?"
"Well you could really use a good pair of jeans."
"I could, could I?" I said amused.
"Yes. You've got a great ass. You need a tight pair of jeans to show it off."
"You really think I have a nice butt?" I blushed. No one had ever commented on my ass.
"It's incredible!" Frank was getting excited. "In fact, you would really look great in a pair of thong panties."
"I don't know Frank." I had never worn thongs, though most of my friends swore by them. They looked like they would be some kind of torture device up my ass. Then again most of women's fashion is torture. Just look at high heels.
"Oh yeah. In fact you shouldn't wear anything but thongs. Those grandma panties have got to go!" Frank was getting very excited. I could feel his erection pressing up against me.
"You are getting so hard," I whispered into his ear.
"I know. I'm getting so hot just thinking of you in a thong and a push up bra," he whispered back.
"I want to fuck you right now." This was unusually explicit talk from Frank, but I had to admit, it was turning me on. I could feel my panties getting wet.
"I wish we could. I want you to do me a favor. Go in the ladies room and take off your panties."
"Frank!" I said with some surprise. I didn't know he could be this naughty.
"Take them off and give them to me."
Normally I would deny such a request, being that I was a little shy about these things, but I had a couple of drinks and I was enjoying his naughty behavior. I went to the ladies room and in one of the stalls I striped off my panties from underneath my skirt.
I felt very sexy walking back to the bar without any panties on under my skirt. When I got back to Frank he held out his hand. "Where are they?"
"Give them to me." I reached into my purse where I had stashed them, and placed them in his hand. He made no attempt to hide them, but brought them to his nose and smelt them.
I could swear that every man in the place was watching Frank smell my panties.
"You're getting me a little crazy with all of this sex talk"
"You want me, don't you?"
"Yes!" I blushed again. He didn't say anything. He just took my hand and escorted me to the back of the bar.
We found a little nook with a small table and bar stools. I sat at one of the stools and Frank moved in between my legs. I had to hike up my skirt a little for him.
Frank kissed me hard and I opened my mouth to accept his tongue. I never expected this type of spontaneous behavior from him. I really liked him, and he was turning me on.
He slipped a hand between my thighs, and before I could stop him, his fingers were at my labia lips.
"Frank!" I whispered, but it was too late. His finger was inside of me. I let out a shudder and closed my eyes. I loved when he touched me, and doing it in the bar was delicious.
Two can play this game, I thought. I reached out while he finger fucked me and I unzipped his fly. After a little manipulation, I was able to get his cock out of his pants.
We were masturbating each other right there in the back of the bar. The place was dark and crowded enough so that no one was watching what we were doing. They thought we were just another couple making out.
But then Frank did something even more unexpected. He hiked my skirt up even higher, and he moved up to me.
"Guide me in."
"Frank no!" I said as he hiked my skirt up so high that you could see my womanhood.
"Guide me in," he said as he rammed the head of his cock up to my lips. With my help, he pushed inside of me.
"Oh God Honey, you're fucking me right here in the bar!"
"You like it don't you?"
"Yes." I admitted as he thrust into me again.
"Is anyone watching?" I looked up from our embrace and at first I could see no one noticing us, but then across the bar I saw a young handsome guy looking at us. He motioned towards us to his date, and she looked up and smiled.
"There's a couple watching us. Should we stop?"
"Do you want to stop?" He asked, but he didn't stop. It felt so good and the idea of them watching turned me on more.
"No," I admitted. Frank was in front of me, so they really couldn't see much, but they knew we were fucking.
"You like them watching, don't you? You little slut."
I watched them watching me, and I actually made eye contact with the guy. Our eyes were locked as I started to orgasm. I think his girl was getting pissed, but I didn't care. In my mind Frank and that good-looking guy were both fucking me, and I came over and over again.
"Oh Cheryl, I'm coming." Frank whispered as I felt his hot come throbbing into me.
Within minutes we had straightened up and were laughing as we ran out of the place. Handsome guy gave me a wink as we passed and his date gave me a "You slut" look.
I didn't care. It was one of the most erotic things I had ever done. Frank was so turned on that we didn't make it back to his place before he pulled over and we did it again right on the side of the road. I started to realize how kinky Frank was.
The next day Frank took me shopping. We must have hit ten stores in two malls looking for a pair of jeans. I tried on at least one pair in each store and had to do the requisite butt check for each pair.
When we did find "the pair" Frank was very pleased. I had to admit that I did look good in them, although I thought they were too tight. We bought two pair.
We also bought a few miniskirts (including a high waisted leather miniskirt which I loved), leggings and a few tops. All of the things we bought were either very tight or very revealing.
That also included the lingerie we bought. It was all so pretty, but it was very skimpy. It took me a few days to get used to the thongs and push-up bras.
I loved it. I loved the fact that Frank was in to my body so much. I had never had a man so consumed by it. It made me feel very sexy and beautiful.
All in all, he spent a fortune on me and my clothes began to fall into one of three categories: conservative stuff that I wore for work or with my family, normal stuff that I wore around, and sexy stuff that I wore for Frank.
Most guys would have a problem with their girl wearing sexy outfits. The problem with it is the unsolicited advances by strange men. But Frank seemed to be comfortable with it.
At first I thought he was just not a jealous guy, but then I started thinking that he liked the idea of some guy staring down my blouse. It turned him on, and I started to realize it turned me on too.
There were many a night that we would be out at a club and Frank would excuse himself to go to the restroom. Inevitably, when he returned, some guy would be hitting on me.
I would tease the hell out of the guy while Frank watched, but I never let it go too far. I would always call Frank over before the guy made his move.
The situation was soon to get way out of hand.
One night in late spring we were at a local bar and we ran into a fellow teacher from our school. His name was Jack and he is the second character in this story.
Now Jack was not only the best looking teacher in the whole school district, but probably the best looking guy I had ever met. He was tall and athletic with light brown hair and smokin' blue eyes.
He was also a major player and he could be very charming. I know, because he charmed the panties off of half of the female faculty; even some married ones.
Now even though Jack was a friend of Frank's and we both worked with him. Jack knew very little about me. You have to remember that at school I dressed very conservatively with my hair up and with my reading glasses on most of the time.
"You're that Cheryl?" he asked after Frank introduced us at the bar.
That night I was wearing jeggings (Leggings that are dyed indigo so that they look like unbelievably skintight jeans), a scoop neck tank top with spaghetti straps, and a push up bra. You could say that my tits were on display that night.
Jack didn't wait very long before he was coming on to me. Now Jack is gorgeous and it was very flattering to have this man flirting with me, but I was uncomfortable with Frank being right there.
Frank on the other hand seemed okay with it. He just stood there grinning while this man just completely ignored Frank and had his hands all over me. Frank even excused himself to go to the restroom, his usual ploy, and left me all alone with Jack.
"I can't believe how hot you look tonight," Jack said as he leaned in to me, and put his hand on my ass.
"Jack, I'm with Frank," I replied, pushing his hand away.
"Frank won't mind," he answered putting his hand back.
"Frank won't mind that you have your hand on my ass?"
"Nah, we're old friends."
"I doubt that."
"Look," he motioned down the bar, "he's standing right there watching us." I looked down the bar, and sure enough, there was Frank.
He didn't even get to the restroom, but was standing down at the other end of the bar talking to someone. He could see every thing we did.
Ah shit, I thought, he thinks that I'm going to flirt with Jack, but I didn't want to. Flirting with some moron I didn't know is one thing, but we both knew Jack, and this kind of thing can go awfully wrong.
I shook my head no to Frank, but he just stood there talking to his friend and smiling like an idiot. Jack on the other hand was getting even friendlier. He worked his way up against me, and I could even feel his erection against my leg.
"Jack, I want you to stop," I barked.
"Relax," he said as he nuzzled my neck, "Frank's all right with it." Sure enough Frank seemed to be smiling even more.
I tried to push Jack away, but he was too strong. He was the wrestling coach, and he had the physique of a wrestler. At another time he would have turned me on, but I was in love with Frank.
Frank on the other hand seemed to be enjoying the show. The final straw was when Jack pushed between my legs, grinding his cock into me, and kissed me on the lips.
"Jack leave me alone," I shouted.
Luckily the guy next to me, who was as big as house, turned around. "Is this guy bothering you lady?" he boomed.
"Yes. Please get him away from me." The guy didn't even have to do anything. He just looked at Jack and Jack backed away.
"Okay, I'm sorry. I didn't mean anything by it." Jack apologized.
I didn't wait around to argue. I just grabbed my purse and jacket and ran down to Frank. I was fit to be tied when I got to him.
"Did you see Jack?" I fumed.
"What's the matter?" He was still grinning.
"He practically attacked me."
"Oh calm down. You're overreacting."
"I'm not overreacting. He was humping me right at the bar."
"I'm sure you are mistaken."
"Frank, I know when a guy is rubbing his cock against me."
"Jack is a friend of mine."
"And he was getting very friendly with me. He kissed me," I said for emphasis.
"Jack's harmless." Frank was oblivious.
"Let's just go." I was livid. It seemed that Jack could have stuck his tongue down my throat, and Frank didn't seem to understand. I was so mad that I wouldn't even let Frank touch me that night. I had him bring me straight home.
All was forgotten until a month later when we were invited to a party at another teacher's house. It was late spring and I wore a miniskirt and a lightweight sweater. It was pretty and sexy without being over the top,
We were having a good time until Jack showed up. I think that he was a little buzzed already.
"Jack's here," I announced to Frank.
"Oh yeah," he replied sounding happy to hear it.
"You are going to protect me from him, right?" I pleaded.
"You're going to start with that?" He said annoyed. I gave Frank an incredulous look. "I promise that you have no reason to be afraid of Jack," he continued. I just gave him another look of disbelief.
Now the funny thing is that Jack paid little attention to me at school. He had apologized to me days after "the incident" saying that I mistook his attentions. I know that I didn't mistake anything, but I thought the issue was put to bed.
Now at the party I was talking to the hostess, Jill, when Jack walked up to us.
"Hi ladies." Jack said smiling. "You two look very pretty today." Jack looked only at me.
"Thank you Jack," Jill beamed. She was one of the married teachers that Jack had been linked to. Jill looked around the room obviously looking for her husband. She spotted him on the other side of the room.
"I'm sorry I have to get something out of the oven." Jill stammered nervously. She didn't want to be seen talking too long to Jack when her husband was around. She made a beeline for the kitchen.
"Jack you're going to be a good boy tonight?" I questioned.
"Cheryl, you are hurting my feelings." Jack answered with a smile. He was very good looking and he could be very charming. Most of the woman at the party would love to be the center of his attention.
I knew that it would go nowhere. Jack only wanted to fuck me because he couldn't have me. If I gave in to him, I would never see him again after her blew his load. I was in Love with Frank and I wanted to be faithful to him.
Jack was very entertaining though, and he kept me laughing the whole night. I kept calling Frank over to be part of the conversation, but he didn't stay long if he came over at all. It was almost like he wanted Jack and I to be alone.
The situation was getting a little weird, and I was sensing that the other women at the party were resenting the fact that Jack was paying so much attention to me.
But to Jack's benefit, he was, for at least for the time being, a gentleman. He kept his distance, and we had a nice night. In fact before I knew it, it was getting late and the party was starting to peter out.
"Let me find Frank," I said to Jack. " I think the party is over."
"What?" Jack replied. "The night is still young. Why don't you guys come back to my place?"
"I don't know Jack." I hedged. With that I saw Frank and called him over. "We better get going Hon. I think our hosts want to call it a night."
"Frank, why don't you two come over my house? I've got plenty to eat and drink." Jack repeated the offer.
"Sounds good to me." Frank agreed.
"I don't know." I said. I had to admit that I too wasn't ready to go home, but the idea of going to Jack's house sounded dangerous.
"Oh come on. We don't have work tomorrow. Let's get a little crazy." Frank pleaded.
"Oh, okay." I agreed, but I still wasn't sure. Jack was being a good boy. Maybe it would be all right.
It was only the three of us back at Jack's place. Frank immediately turned on the TV and started watching some old movie. That left Jack and I alone in the kitchen.
There was a large mirror in the living room so I could see him clearly, and most importantly, he could see us. Jack started out all right, but we kept drinking and we were both getting a little tipsy.
As Jack got drunker, he started to get closer and friendlier. Damn, if Jack wasn't drop dead gorgeous. I had to admit that I was enjoying his attentions. Frank could see everything we did so I felt safe, but not for long.
"Cheryl I can't believe that you are the same woman I work with at school. You look so hot tonight." Jack started his move.
"Knock it off Jack. You said you were going to be good."
"Oh I'm very good." Jack was right on top of me. His eyes were so gorgeous. If I were not in love with Frank, who was sitting in the next room, I could have easily let him have his way with me.
"Jack stop," I complained loud enough for Frank to hear, but he went on watching TV. I wasn't sure if he was watching the TV or us.
Jack didn't stop though, and soon he was between my legs, nuzzling my neck. His hands were on my hips.
"Jack!" I protested, but I didn't try to stop him. The fact that I had a little too much to drink, and that Frank had paid so little attention to me that night, clouded my judgment.
I decided right there that I would see how far Frank would let Jack go. I figured that all I would have to do was let Jack kiss me a few times and Frank would come storming in.
It was as much as a surprise to me, as to anyone, that when Jack kissed me and stuck his tongue in my mouth, I actually met it with my own tongue. We were French kissing like mad before I had a chance to stop, and Jack took that as consent.