Emily the Tease Ch. 04

I knew the time had come to confront my beautiful girlfriend Emily. Here I was a grown man, working hard to please my girlfriend of over a year and she had still not fucked me. Worse I had had to watch her fuck an old boyfriend, and I suspected there may have even been others. I knew Emily was out of my league when I started dating her, but it was time to stand up for myself.

To be fair, I did love being with Emily. It was very exciting when I got to kiss her and touch her soft skin. And she had let me kiss her perfect ass. I knew I deserved even more, but it was very hard to risk it all. I had never been with a girl anywhere near as gorgeous as my Emily.

One evening after we were out with her friends (Emily was very social and she generally liked to hang out with a group of her friends rather than just the two of us), I drove up a few doors before her apartment where it was quiet on the street. Sometimes Emily would let me make out with her in the car before she went up to her place. I knew I had to confront her now or I never would. I told her we had to talk and she asked me what was wrong.

"Well...Emily...I..."

I stammered and stuttered but finally managed to tell her I felt like I needed to be more intimate with her.

"I really try hard to please you Emily. I think I deserve more."

Emily was very sympathetic.

"Oh, poor baby." She stroked my hair. "I know you try to please me and I suppose you do deserve more. It's just that I fell into so many relationships so quickly and I don't want to spoil what we have."

She kissed me soft on the lips and I felt my resolve fade a little as I hardened.

"Mmm...I know something that you might like." she said in a teasing voice.

Emily reached under her skirt and I watched with my mouth open as she lowered her panties down her smooth legs and over her high heeled shoes. She reached over and gave my cock a squeeze. My heart was beating fast.

"Why don't you...give me a kiss here?"

Emily pointed between her legs a little shyly. I was a little unsure we should do this right on the street, but the windows were tinted and I was grateful and excited that she was taking our relationship to another level. I bent over and kissed her pussy through her skirt. I remembered how smooth and tight it had looked when I had the chance to see it at the party. Emily stroked my hair and raised her skirt slowly revealing herself inch by inch while seeming to enjoy the desperation in my eyes. Her pussy looked even better than I remembered. I kissed it again and felt my cock push against my pants.

Emily murmured her approval so I continued, covering her pussy with kisses. I started to lick, but found it awkward from the other side of the car. Emily moved the seat back and I knelt in front of her on the floor. I licked up and down, then started to push my tongue into her. Emily writhed and moaned. When she seemed to really enjoy something I was doing I would do it again and again until she seemed to tire of it. Finally one time I was licking high on her clit and she grabbed the back of my head and pushed my face into her. I could barely breathe but I used my tongue desperately, trying to make her cum. She grew louder keeping, my head pushed into her until finally she became quiet while grabbing my head even tighter. I felt her juices flowing all over me and tried hard to lick them all up.

Emily laid back catching her breath. She kept her hand on my head so i stayed there cramped on the floor and looked up at her face. It made me so happy to have pleased her. I noticed she had a little sweat on her forehead and kissed her thighs gently.

When Emily gathered herself she asked, "Did you enjoy that?"

I nodded ascent and she smiled "Good, I told you that you would."

With that she bent forward, kissed me on the cheek, put her panties in her purse and left the car. "See you soon!"

I watched as she walked to her place, admiring her ass swaying. It was exciting knowing that she had no panties under the skirt. I was rock hard and hurried back to my place to jack off.

After that night a new world opened up for me. Emily let me go down on her over and over again. Sometimes before we met up with her friends she would come to my place and before we'd even said much I'd find myself on my knees while she laid back and gave herself to me. It wasn't easy to please her, but I became better and better with practice. Sometimes on a lazy weekend she would catch up on her tv shows while I licked her pussy gratefully. Other times, after we went out with her friends she would let me park the car behind the hospital near her place and get in my familiar spot in front of the passenger seat to go down on her.

I was so horny that I found myself jacking off more than ever. Over time, I wondered if Emily was still taking advantage of me. As much as I enjoyed pleasing her, she never returned the favor. She did let me jack off in front of her sometimes when we were at my place, but usually she would want to do something else after I had made her cum.

I didn't have anybody else to really confide in until I thought of Isabel. Isabel is an old friend of Emily's, but I now consider her my friend as well. She is Latina, and much less attractive than Emily. Isabel carries at least 20 pounds too many on her, but she has always been nice to me. Actually Isabel is the only person I have fucked in the past two years, when Emily allowed me to do so as a birthday gift.

When I arrived at Isabel's door she greeted me warmly with a hug and a kiss on the lips. I felt her big boobs push into me and tried to think of something else when my cock responded. Isabel poured us both a scotch and we drank and made small talk a while.

Finally she asked sweetly, "So, you said you wanted to talk to me about something?"

I hesitated at first but when I started to tell her the words wouldn't stop. Isabel moved closer to me and squeezed my hand while I went on. I told her how obsessed I was with Emily, how I had tried so hard to impress her. I told her about watching her get fucked by her old boyfriend, and not saying anything. I told her I had now become Emily's oral servant, which I enjoyed but wondered if I was pathetic to settle for this.

"Aw Ian", she started, rubbing my shoulder, "stop thinking so much."

I looked at her a little confused.

"You know you're lucky to be with Emily, right?"

I nodded, my face becoming a little red with shame.

"I mean she has been with a lot of guys before. A lot. But never any as long as you."

I brightened a little. "Really?"

"Really. And she always made the same mistakes. She would fuck them on the first date, sometimes she would even fuck them at the parties where they met. I think she is just determined not to make the same mistake with you."

Isabel was stroking my leg now, and as she brushed my inner thigh I grew worried she might notice the erection that had formed with talk of Emily fucking, and Isabel's soft touch.

Isabel looked me in the eyes. "You think you can be patient for her?"

As I nodded, Isabel's hand ran along my thigh until it grazed my balls. She stay locked on my eyes as she ran her hand along my hard shaft. I whimpered, I hoped inaudibly.

"Good. And you know I can help you if you need, right?"

Isabel didn't wait for an answer as she unzipped my jeans, took out my cock and started to stroke it.

"Thank you." I whispered.

Isabel smiled a big smile as I watched her lower her head on to me. She took my cock deep in her throat again and again. I moaned how good it felt and she sped up. I watched her head bob up and down until the sensations became too much and I closed my eyes and shot into her. Isabel kept me in her mouth until I finally got small and fell out.

I was so grateful to Isabel for being such a good friend. I felt compelled to return the favor, and Isabel seemed happy to let me reciprocate. Before I knew it I was between her big thighs, licking her like it was my last ice cream. Isabel was mush easier to please then Emily, and she groaned loudly. I felt my chin push into her big opening as I tried to apply everything I had learned from Emily. When Isabel came she squeezed me between her legs, deafening me. I closed my eyes so the only sensation I had was her pussy on my tongue.

I was glad I had pleased Isabel, even though it did not give me the same high as when I pleased Emily. It was simple with Isabel. She was my friend there to support. With Emily it was more complex. I had a deep need to be with her, to make her happy. Later that night when I looked at Emily I felt more at peace. We were not equals, but Emily had decided to be with me and I was grateful. I smiled at her in what I imagine must have been a sappy way.

"Michael is in town." she said suddenly.

"Michael?" I asked. My stomach sank as I remembered lying in bed, watching Emily on her knees sucking Mike's big cock.

"Yes, my ex, you remember? He's actually be just out of town at a resort. He's there on business for a week. He invited me to go up and visit him there."

My stomach turned. Was she telling me she was going to go away and see her ex. boyfriend?

Emily continued, "Ian, I do want to see him, but I'm afraid of falling into old patterns with him. I mean he's always been able to get me in bed so easily."

I looked at her, eyes wide, wondering where this was headed.

"So...I was thinking, you and Isabel could join me. Help make sure I behave?"

As strange as this was, I was relieved. Emily was being honest with me, and she wanted to stay true. I'd certainly rather she not see Michael at all, but I knew Emily was headstrong.

"Yes..." I started, "I mean if you want to see him I'll go with you...and I'm sure Isabel would be game."

"Goody!" Emily exclaimed as she kissed my cheek. "You're such a good friend. We'll leave tomorrow morning and spend the weekend.

I wasn't sure why Emily thought it would be so easy for me to take Friday off at the last minute, but I couldn't argue. I needed to make sure to be there and help my girlfriend 'behave'.

The next morning I found myself driving Emily and Isabel out of the city to the nice resort Mike was staying at. I knew many boyfriends wouldn't drive their girlfriends up to visit their ex., but when I looked in the rearview mirror and saw Emily's beautiful face I knew it was the right choice. Emily was in the backseat texting while Isabel sat in the front seat beside me. We played Emily's Ipod selections, with me skipping songs she didn't want to hear.

Isabel smiled at me and stroked my leg. I was a little self-conscious about what Emily might think, but she was not paying any attention. Besides, Emily had let me fuck Isabel before, so I assumed she wouldn't mind her touching my leg. I felt myself harden from her touch. Isabel wore jeans and a tight t shirt. Nothing special but her huge tits were certainly distracting as I drove. Emily was more dressed up. She wore a little blue dress that showed a lot of leg with blue shoes that complemented it nicely. I angled the mirror and could see lots of smooth skin and my dick throbbed and a little. Perhaps, I thought, I'd get to fuck her this weekend.

The resort looked very nice as we approached. Emily seemed excited to get the chance to stay for the weekend. I decided to park myself and save the valet charges. I dropped the girls off at the lobby and saw that Michael was there waiting. Emily must have texted him to let him know we were close. I waved to Mike but he didn't see me. I watched as he gave Emily a big hug. His hand went down to her ass and gave it a squeeze through her little dress. I realized he might also be victim to old habits. I hadn't asked Emily if he still had a girlfriend. I hoped so.

A man from the hotel was waving me away from the entrance, so I drove off to find a parking spot, leaving my girl in Mike's arms. It took me a while to find a spot, and then I struggled getting all of our bags to the hotel. By the time I got there I found Isabel but no sign of Emily or Mike. My heart leapt a little but Emily explained that Mike had taken the liberty of canceling the room Isabel, Emily and I were going to stay in and instead upgraded his room to a two bedroom suite. He had headed up to show Emily the room.

Isabel took her bag from me and as we walked to the elevator I explained that I had promised to help Emily avoid being seduced by Michael.

"Oh, good idea." Isabel said as we waited for the elevator. "Michael used to have quite the hold on Emily. You would be amazed by some of the things he had her do for him."

I felt myself harden at the idea of Emily having crazy sexual adventures but at the same time I was concerned about the two of them being alone. I wanted to ask Isabel about what Emily had done but the elevator arrived. I pressed our floor and Isabel tried to relax me.

"Try not to be anxious Ian, you know Emily likes her space."

I nodded, knowing Isabel was right. Isabel reached over and squeezed my semi erect cock as she gave me a kiss. "...and if you ever need a little relief I am sure I can help you with that."

I blushed despite myself. I had never had a relationship like I had with Isabel and sometimes was unsure what was appropriate.

When we got to the room I was relieved to find both Mike and Emily fully dressed. They were sitting close together on a plush couch in the main room. Mike's hand was on Emily's bare leg, but I figured this was nothing to get uptight about. Emily certainly looked gorgeous and I could understand Mike wanting to touch her.

"Beautiful place!" Isabel exclaimed. It was indeed. The main room was large with tall ceilings and big windows that overlooked a ravine. There were bedrooms on either side of the main room and Michael showed us ours. It had one king sized bed, and I wondered how the three of us would manage tonight. I placed our bags in the room and Michael handed me a beer. I saw he had already opened a bottle of good wine as he poured Isabel a glass and Emily a refill.

We sat in the lovely suite and drank for the afternoon. Isabel and I sat across from Michael and Emily. It felt rather awkward for me that my girlfriend was sitting with another man, especially when he would allow his hand to roam along her leg, but everyone was so relaxed I decided it was better not to make a fuss. The drinks flowed and everyone was feeling a little buzzed. Mike pulled out some weed and we all took turns smoking. At one point Emily giggled at how Mike and her used to sometimes smoke a full day away in her little dorm room. He reminded her how he used to have her help him smoke and she giggled more, then took a long toke and showed Isabel and I how she would put her lips against his and let him take in the smoke from her mouth. As I watched my girl pressed her lips against her those of her ex., I felt rather jealous, but I was also excited. I could feel my cock growing. When Isabel tried to see how it would work on me I grew even more excited with her tits pushed on my chest as she pulled my head towards her and pressed her lips on mine. My hard-on was now pushing against my jeans.

After our tokes I noticed that Emily was now cuddled in with Michael. His arm was around her, resting on her ass cheek, and her head rested on his big shoulder. One of her legs was on his. I knew this must be an old habit that Emily had wanted to avoid but I figured as long as I was here I could help to make sure it didn't go any further. When Isabel rested her head on my shoulder and I felt even more assured that everyone was just mellow from all the drinking and smoking.

We all realized we were hungry. Michael said there was great pizza at the restaurant in the resort. All agreed that sounded great. Mike said that he could go down and get it, but since he paid for the room I volunteered to have Emily and I pick it up. On the way out Emily said she had to pee. I stopped to wait but Isabel said she'd go with me. As we headed out I realized I was leaving the two of them on their own but I knew it would just be a few minutes.

When we got in the elevator Isabel grabbed my cock through my jeans. "Somebody is feeling a little horny!" she taunted as she squeezed the hardness. She started to stroke back and forth as she looked me in the eyes.

Part of me wanted to fuck her right there, part of me wanted to run back to Emily and part of me wanted to lie down and take a nap. The doors opened and instead of any of these options, I went with Isabel to get our pizza. Perhaps because we were rather buzzed it took us a while to find the restaurant, and when we did they told us it would be 15 minutes until the pizza was ready. I panicked a little at the thought of waiting all that time. I texted Emily to let her know we would be back soon and she texted back saying 'good'. I felt a little relieved that she had responded, but while we stood in the lobby waiting for the pizza to be ready I began to feel anxious again. Emily was also stoned and Mike had had his hands on her since we had arrived. Where might his hands be right now? I felt myself harden as I imagined him grabbing Emily's ass, but I also felt my stomach turn.

I realized Isabel was talking to me and I hadn't heard a word she was saying. I nodded dumbly when she had apparently asked me something and she laughed and said I was 'such a goof'. Suddenly she pushed me against the wall and kissed me hard. I felt my cock push against her as she grabbed the back of my head as her tongue probed my mouth. I also felt my worries fade as I lost myself in her. It felt good to give up control. Isabel was a good friend.

I'm not sure how long she kissed me like that, but when she stopped she took my hand and walked me back in the eatery to get our pizza. I was calmer now but still anxious to get back to our room. When we walked in my heart sank at not seeing either Emily or Mike. As I put the pizzas down I heard Emily giggle. I turned and realized she was in Mike's room and the door was shut. I took a step towards the door but Isabel grabbed my hand.

"Just give her some space Ian." Isabel said firmly but patiently, as though teaching a child.

I paused, unsure of what was appropriate. Emily had asked me to help make sure she didn't fall into old patterns, but I knew she hated it when I was jealous.

I heard Mike's baritone voice followed by more giggles through the door. Isabel directed me to the couch and we sat down.

"All right. I'll show you but you can't touch." I heard Emily say. I was a little encouraged that she was putting boundaries in place but in my heart I knew where this was headed. I heard his deep voice followed by her giggles. She chastised him in a way that made it clear she was not upset at all "Miiiichael!"

I shuffled anxiously and Isabel placed a firm hand on my leg to relax me.

"Oh god you're so hard!" Emily said incredulously. I noted that I was also hard as I wondered if my girlfriend was just looking or also touching.

The sounds from the other room became a bit muffled, but it was clear there was some kissing going on. Then I hear the clear slaps of a spanking, along with Emily's yelps. Despite the fact that I knew another man was enjoying my girl, I couldn't help but be turned on. Isabel's hand reached over and started to gently stroke my cock through my pants.

The spanking stopped and Emily's yelps had turned to whimpers and purrs. I imagined Mike might be fingering her. I heard his low voice with what sounded like reassurance or instructions.

The next sounds made it clear that my Emily was getting fucked. Hard. We could hear the bed shake with a thumps. Isabel had taken my cock out of my pants and was stroking it to the rhythm of Mike's thrusts. I felt some outrage at sitting there having to listen to him fuck my girl, but I was also incredibly turned on. Emily and Michael seemed to be making no efforts to keep quiet now. Emily was squealing with pleasure and Michael was grunting and at one point said something followed by "little slut". Finally, as I could hear the familiar (but more intense) sounds of my girlfriend about to cum, I felt like I couldn't hold back. I bent my head down and kissed Isabel's shoulder while I shot all over her hand.