Emily the Tease Ch. 02

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Boyfriend can't resist Emily's teasing.
3.3k words
4.37
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Part 2 of the 5 part series

Updated 06/08/2023
Created 07/19/2013
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Things were even better between Emily and I after the night we all went out dancing. She still wouldn't let me make love to her, but I would at least I get to release sometimes. A few weeks after we had been dancing at the club, things had got pretty intense in my car outside her dorm when it was time to drop her off. We had been making out for a few minutes when she straddled me and we started to dry dry hump while I held on to her amazing ass. I thought I might be able to convince her to come back to my place, but it didn't take long until I came in my pants. Emily kissed me on the cheek and headed up to her dorm.

I also got a treat a month later, on her birthday. She had asked me to take her to the best place in the city, which I was glad to do. I was little disappointed when she said she wanted to bring several friends along. Aside from not having Emily to myself, this meant the bill would become awfully high.

That night we had several rounds to toast the birthday girl. Emily sat across from me but spent much of the night talking to Barry, who sat beside her. Barry was an old high school friend of Emily's, and even though I knew they were just friends, I had always been jealous of how close they were. The two of them often whispered little secrets to each other which would often result in Emily giggling and touching his biceps. That night I noticed Barry's hand on Emily's bare leg and I made a note to talk to Emily about it later.

Seated next to me was Emily's best friend, Isabel. Isabel was a nice girl, and very sexual, but rather unattractive and a little chunky. Isabel had been flirting with me all night, which at times was a nice distraction from trying to see what Barry and Emily were doing.

When the bill came I was a little shocked at the cost. Eight people celebrating at a nice place can add up quickly. I was happy to please Emily, but felt like the others were taking advantage of me a little. I reluctantly reached for my credit card and as I did so I felt something move up my leg, and into my lap. I looked down and saw five of Emily's pretty painted toes wiggling up at me. She pointed her foot down into me, and I immediately hardened from her touch. I looked at Emily and she winked naughtily while starting to stroke me with her foot.

Brad distracted her by offering some of his dessert and she happily accepted, wrapping her lips around his proffered spoon and getting a little whipped cream on them. She didn't miss a beat in stroking me though. I started to feel like I was going to cum and fought to avoid doing so, since this was a very fancy restaurant, and I was wearing my only suit. Emily's feet seemed rather expert at this, however, and she pushed against me in a glorious, merciless way.

Isabel must have noticed what was happening, because she laughed and whispered in my ear how lucky I was to get a gift on Emily's birthday. When Isabel pushed her tongue into my ear and gave my nipple a hard tweak through my shirt, I immediately started to shoot into my pants. Emily could clearly feel what was happening, and drained me with her foot before removing it from my lap. I breathed out deeply, then flushed when I saw the waitress beside me, checking to see if I was ready to pay.

I was rather humiliated leaving the posh place with a clear stain in my light gray suit, and was uncomfortable the rest of the night with the mess in my pants, but I did fantasize about this again and again when I was alone in my apartment, masturbating.

As it happened, my birthday was only a few weeks after Emily's. It was obvious what I wanted for my birthday, and I was hoping Emily, who hadn't had a lot of time for me lately, would let me take her away for the weekend.

It turned out that we did go away on my birthday weekend, but it was to a friend's house on the lake. There was a reunion party for the graduating class at the college Emily attends. Even though she was two years behind, she knew a lot of people who would be there, since her boyfriend last year had been in that graduating class.

It was only on the drive to the house that I learned her ex was going to be there himself. She hadn't seen Michael since she had broken up with him Thanksgiving weekend, and I had almost forgotten about him. I had only seen him one time, the night I first saw Emily. He was a star football player in college, and a very different build from my more 'yoga-like' physique. I started to ask her if it was a good idea to see him again, especially on an overnight trip, but knew she didn't like it when I cam across as clingy. Emily reached over and lightly stroked my cock through my shorts, telling me not to be mad at her, and reassuring that we'd have a good time.

It was actually Michael who greeted us as we pulled into the driveway and got out of my car. He hugged Emily close and kissed her on the cheek "So good to see you Em, you look fantastic."

He turned and looked me over, "So this is your friend?" He shook my hand, engulfing mine in his "Hey, good to see you dude, welcome." He walked inside with Emily while I got the bags out of the car. Overhearing their conversation, I learned that this was actually his brother's place. Emily hadn't mentioned Michael was hosting.

The rest of the group was already there, 13 in total. They were three years younger than me, but since many of the men were gig guys, former jocks, I somehow felt like I was a junior at a senior party. The beer was already flowing and Michael tossed me a can while he caught up with Emily and poured her some wine.

I met a few people in the group, including Michael's girlfriend Kimberly. She was an exotic mix, with long black hair, dark brown eyes and gorgeous olive skin. Kim was wearing short denim cut-off that showed off her legs, and a tight white shirt that made it evident she was not wearing a bra to support her firm breasts.

I found myself fumbling for words when I felt Michael's big hand on my shoulder "So I see you met Kim." He laughed as if it was obvious to everyone that I was amazed at Kim's body. I felt my cock twitch and heat rise to my face as I looked down sheepishly.

Michael introduced Emily to Kim and the two kissed each other's cheeks and sized each other up. There were a number of attractive women at the party, but these two stood out, and guys around the party were clearly enjoying having them around.

Emily seemed to know most of the people there, and I felt out of place as I watched her hug the guys and girls around the room, smiling her big smile. I only knew Isabel who had arrived on her own, and I found myself staying close to her for support.

A couple of hours later, many rounds had been drunk, and everyone, including myself, was feeling no pain. Emily had stripped down to her bathing suit, even though it was now dark out and it didn't seem she was going swimming. She plopped herself down in my lap while we talked with a couple she knew, and I felt myself harden immediately as her ass cheek pressed against my bare leg.

Soon, however, Emily was beckoned over to the group beside us. Dan, Michael's best friend, told Emily they just had to catch up, and patted his lap with what seemed like a leer. Emily rose, giving me a great view of her half covered ass, then moved over to her old friend, sitting in his lap while he put his arm around her and started talking old times. I felt a longing and some anger as I pretended not to look. I was actually happy when Isabel came over and put her big ass on the arm of my chair, my view of Emily now blocked by Isabel's big tits. I downed my drink and scolded myself for feeling so jealous.

Of course when old friends get together old times are discussed, and I started to hear stories of Emily's wilder days. Apparently she was know for disrobing after a number of drinks at social gatherings. Michael and Dan started to tease Emily about this and encourage her to give everyone a show. Michael told a story about one night when they needed some cash for a coming concert, and Emily had offered to flash her tits to anyone at the party for $10. They had made $160 that night, although he noted there may have been some groping involved. Emily seemed embarrassed, but also a little excited by all the attention. I noticed that her bathing suit had ridden up her ass so it was now basically a thong and wondered how and when that had happened.

The crowd seemed anxious for a show. Shots were poured and everyone drank them quickly. Michael came and handed me another one quickly, playing the warm host.

Emily was firm that she would not take off her top, but giggled when a spontaneous collection reached $80. Kim seemed pissed to have all the attention taken away from her, and announced that if they could get the pot up to $200 she'd take her top off for rest of the night. It took about thirty seconds for the guys to throw the money on the table and another fifteen for Kim to slowly remove the t shirt that had (barely) been covering her impressive breasts. The room erupted in cheers as she turned to make sure everyone got a good look. I was hard just staring and could see at least two more impressive bulges on the guys around me.

Dan laughed that Emily had missed her chance to be the star of the show and Emily gave her lips a pout. Dan then loudly announced that Emily would still get her moment in the spotlight, because it was time for her birthday spanking. Emily started giggling uncontrollably, apparently this was some kind of an inside joke... but Dan quieted her with a hard swat against her left ass cheek. Emily protested, but Dan and another guy each grabbed a hand and bent Emily over over Dan's lap. Emily's nearly bare ass was now available for anyone and two guys took turns with solid swats with their bare hands.

I started to get up to stop this, but Michael placed his big hand firmly on my shoulder and gently pushed me back down. I shook off a little dizziness, then looked over and saw that Emily was no longer being held down, but was keeping her ass raised and was accepting swats from most of the guys and several of the girls. Her pale ass cheeks reddened brightly as hand after hand spanked her, sometimes just groping a cheek. Finally Michael laughed and said that was enough kissed Emily on the cheek, and stroked her ass soothingly telling her he was sorry he didn't send a birthday card.

Kim seemed to decide it was better to join in the fun, and offered to pay Emily half of the $200 she had earned if Emily would lose the bikini bottom. Emily laughed and sensibly refused. Soon though Kimberly's offer was matched Dan, who was egging Emily on, telling her that she had already shown her ass to everyone and had half the room had felt it.

Emily looked at me, then looked at Michael, finished her shot of tequila, then shocked me by very slowly pulling down her bathing suit bottom, exposing a round, perfect ass I had never seen in its entirety, and well as a completely shaved pussy. I was incredibly turned on, but also angry that I got to see my girlfriend naked at the same time as everyone else did.

Things moved pretty fast from there. The room was cheering and drinking, some taking pictures of these two beautiful, half naked girls. There was money all over the room. I saw Isabel making out with some guy while Michael gave me yet another shot.

Suddenly Emily and Kimberly were kissing, Kim's hands grabbing Emily's ass aggressively enough that those behind Emily got a good look at her asshole. It was incredibly turned on by the sight, even though I could just look at them through a haze of drunkenness from my chair. They were both so beautiful, a sexy fantasy come to life, even if they were surrounded by drunk, cheering jocks.

Finally I couldn't take it any more. Emily and I had been given our own room, the only couple other than Michael and Kim to get one to ourselves. Sure, it had two beds, but I had still held out hope that tonight might be the night. At this moment, however, I just needed to jack off and relieve myself. I shut the door, and, unable to stabilize myself, lied in my bed. I grabbed some kleenex and jacked off thinking about Emily's ass and Kimberly's breasts. I came quickly, then passed out, exhausted and drunk.

I awoke to Emily's hand on my shoulder, shaking me gently. The room was dark and the house was much quieter than it had been. It seemed that the party had wound down. I realized that under the sheet that covered me, my pants were down and I was lying on kleenex filled with my cum. My heart beat fast at the thought of Emily finding out I had left the party to jack off. I pretended to be asleep to avoid exposing myself. Emily shook me harder, then gave up trying to wake me. She left the room for a moment and I breathed a sigh of relief. I may not get to make love to her tonight but I had at least kept my dignity.

Almost immediately, however, Emily came back in the room, this time with Michael. I kept my eyes closed as they shut the door. I pretended to be knocked out, and truth be told I was pretty out of it. Perhaps she had brought Michael to check on me because she was concerned?

In the dark, I could see that Emily was still bottomless. She stood close to Michael, just a few feet from my bed and took off shirt while kissing him. Michael then guided Emily to her knees, and she unzipped his shorts. He reached to the back of her head and pushed it gently towards him and took his large cock in her mouth. Michael groaned and she shushed him, giggling before taking him into her mouth again. She seemed to savor every inch of him as she licked up and down his shaft.

Soon he had her bent over the other bed, her ass raised for him. I saw him stuff his cock into her easily while she bit her lip. I couldn't believe I was watching my girlfriend get pounded from behind right beside me, but I couldn't say anything. He fucked her like that for 10 minutes as she tried unsuccessfully to keep quiet and finally I could hear him cum into her. They kissed and then Michael left quickly, I assumed to get back to Kim. The shock of what I had seen had sobered me up, but I lay there still, watching Emily clean up herself and the room. She left and I lay there alone, unsure of what to do, paralyzed by indecision. Was Emily was coming back? Should I go confront her? Perhaps I should just get in the car and go? I laid there, my mind racing,

Emily finally returned with a towel wrapped around her, freshly showered. She walked over to me and shook my shoulder gently. "Ian?"

I pretended to rouse slowly and she smiled sweetly and kissed me on the lips. Her breath was fresh from toothpaste, which was something of a relief. "Oh Ian, I have something to tell you."

My heart sank, as I feared she was going to tell me it was over. I realized at once how good Emily made me feel, and my heart sank at the idea that I couldn't be around her. "Ian...I...kissed Michael."

I opened my eyes a bit wider and she continued, "I know it was wrong, I was just so drunk, and...well, we had been close for so long."

Emily looked so genuinely sorry and concerned that I had to reassure her. "It's ok," I said, "I understand you...might have slipped into an old pattern."

"But it's your birthday!" she said emphatically. "What kind of a friend am I to do that with you here?"

I was speechless, then saw her smile. "I did plan something for your birthday though. I know you'll like it." I got excited despite myself. "I know I have resisted sleeping with you, and I don't want that to change tonight...but I thought I could still give you something special"

Emily left the room and my mind raced. I realized that if she was going to give me a blow-job like the expert one she had just given Michael, I would probably forgive everything. She re-entered with Isabel by her side, also wrapped in a towel, freshly showered. "Surprise!" she said "a 'threesome'...of sorts!"

The two of the crawled beside me in the bed and they both kissed me. "Happy Birthday" Isabel whispered. They pulled down the sheets and revealed my now hard cock. Isabel laughed as she tossed the kleenex away and puled my pants off my legs. "Looks like you have been giving yourself a good time!"

I felt my face flush with shame, but forgot it quickly when I saw that both girls had removed their towels. I got my first good look at Emily's tits. They were small, pert and had the pinkest nipples. I reached up and sucked on one as Isabel stroked my cock.

"Now, I'm so tired from all the drinking and dancing..." Emily said sweetly as ran her fingers through my hair "but I know you adore my ass and thought I'd let you kiss it."

With that she stood up on the bed, placed her hands on the wall, and proudly bent forward, arching her back so her ass was offered me to. I knelt behind her and at first just took in it's perfection. Then , I gave a gentle kiss, followed by another and another until I was covering her ass gratefully in kisses. "Mmm...you love that don't you?" Emily teased as she pushed her ass cheeks back into my face smothering me.

Isabel positioned herself beneath Emily's legs, facing me, and took my cock in her mouth. I hadn't received a blow job in over two years, but this far exceeded anything I has enjoyed. Isabel was all tongue, and knew exactly what to do to make me crazy. Since I had cum not long before I managed to hold back and continued to kiss Emily's firm ass. As I buried my face in her bum, Emily reached back and pulled her ass cheeks apart, "That's it Ian...kiss my asshole." I moaned Emily's name and came violently into Isabel's mouth. Isabel swallowed ever drop before releasing me, while I breathed heavily onto Emily's ass.

It had been such a long, confusing night, but at that moment I could only feel grateful to have a girlfriend like Emily to celebrate my birthday with.

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AnonymousAnonymousabout 1 year ago

OMG! This was quite an advance. Emily gets naked in front of everybody at the party and fucks her old boyfriend.

Ian ends up worshiping Emily's ass and kissing her asshole. Emily is finding her female power and is emasulating Ian.

My wife took me down a similar road early on in our relationship. It's a one-way road and there is no way back. I adapted well, and hope Ian can too!

Great story!

AnonymousAnonymousover 10 years ago
More please!

Anxiously waiting...

SoleBrotherJeffSoleBrotherJeffover 10 years ago
Walk Away Now, While You Can

It has been my experience that most women do not know the full power to their female control of the male libido.

But those that do, like Emily, take full advantage of their prey.

The male has to reach a point where he knows he has to just walk away to save his sanity.

Walk away now !! She is using you like a puppet.

Sole Brother Jeff

AnonymousAnonymousover 10 years ago
Good

Wonder how this could evolve. Nicely done.

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