Emilys Friend

Prologue

This is the third in the My Emily series. Look for me under AUTHORS and look at the others.

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Emily had sure been on my mind for the last couple of weeks and now I had a reason for going back. Emily had said over the phone that she had something she wanted to talk about the next time we were together, and then would say no more about it. She certainly had my curiosity aroused -- could she possibly be pregnant? I thought that the pills were supposed to be almost foolproof, but I guess that nothing is 100%. Please don't let it be that!

The cover story that I told my folks last time worked pretty well, so I was sort of planning on using that ploy again on this trip. So here I am again, heading back to my home town on a Friday afternoon with another bottle of Chardonnay to see one of the sweetest girls I had ever known (and to find out about the "big mystery").

I arrived about 5:30 and Emily met me at the door dressed in a pair of shorts and a T shirt. This time I had presence of mind enough to put the wine in the refrigerator before joining Emily on the sofa. Without saying a word, she started off by giving me a long, passionate kiss. Her tongue played games with mine and I did the same with hers. She started to move her hand up my shirt and began gently rubbing my chest in small circles with her fingers.

I removed her T shirt and took her beautiful breasts in my hands. I started with Emily's left breast, and began kissing the nipple and bathing the aureole with my tongue. I slid one hand down into her shorts and I started to massage her lovely ass cheeks. She gave off some low moans, so I moved my hand around to her Venus mound and slipped one finger into her pussy and then gently rubbed her clit. She spread her legs for me and buried her face in my neck.

"Don't stop, Chucky, keep touching me. What you are doing feels so wonderful." she said, as she started to gently blow into my ear, sucking on my earlobe at the same time. Remembering how it went the last time, I unbuttoned her shorts and started to remove them. Emily quickly came to my aid, removing her shorts and her thong and throwing them on the floor.

I changed my position and began kissing the inside of her thighs, moving my tongue closer and closer to her pussy. I used both of my thumbs to open her pussy lips and started to slowly lick her most secret places. I inserted two fingers into her pussy and began to suck on her delicate little clit as it peeked out of its hood. She moaned more intently, begging me not to stop. Her movements became more frantic, by now she was clawing at my back and her sweet juices were flowing around my fingers. Her legs tightened around my ears and she arched her back as a tremendous orgasm swept over her. She uttered her usual, "Ugh, ugh, ugh" before collapsing in limp disarray on the sofa. I continued stroking and sucking as she gently came down from that most wondrous feeling.

After a few minutes, Emily moved down to the floor and undid the fastening of my shorts, sliding the shorts and my boxers down around my ankles. My manhood immediately sprang up, ready for action. She put the tip of my cock in her mouth, sucking gently and licking the head, while moving her hand slowly up and down my shaft. I watched in fascination as she took more and more of my cock head between her lips and started to suck. She kept her eyes open, watching my reaction as her tongue teased and stroked my throbbing erection.

"Take it easy," I said in a quavering voice, "I'm ready to cum already." Emily only took me deeper into her mouth. She increased the suction as she stroked me with her tongue, breaking contact only long enough to come up for air.

"You give unbelievable head," I said, "But I'm gonna cum if we keep this up—", I warned. Emily opened her eyes to look at me, her nostrils flaring as she struggled for breath, and sucked harder. My cock started erupting and Emily grabbed me, pulling me closer as I emptied my whole load into her mouth. She amazed me by swallowing all that I had ejected and then smiling up at me mischievously. With that done, she picked up her clothing off the floor and I pulled up my shorts as I followed her toward the bedroom.

We made a brief stop at the bathroom and then went into the bedroom. Emily walked over to me and started to take off my shirt. I helped her get it off and then I dropped my shorts and boxer shorts once again and kicked them away. Emily then lay on her back on the bed and started stroking her wet pussy.

"Oh Chucky, give me what I've been missing every minute of every day," she murmured, as she looked up at me with her pretty blue eyes.

I positioned myself between her outspread legs and rubbed my stiffening prick up and down between the lips of her pussy. I could tell she was ready for me because of the moisture I was feeling, caused by my movements between her clit, her pussy, and her anal opening. Emily reached for my now fully hardened dick and inserted the head into her pleasure pit and I completed the action with a slow steady insertion all the way to the hilt. Her pussy was nice and tight around my cock. I began moving in and out at a slow, measured pace and soon she began to thrust her wet and warm pussy up to meet my every stroke.

After a few minutes of gentle love-making I guess she was ready to explode. "Lover, I'm going to cum -- are you ready?" she exclaimed breathlessly.

I wasn't, but since she was about to have one well-deserved orgasm I wasn't going to ruin the moment.. She arched her back and I could feel hot juices lubricating my cock.. I stopped my thrusting and collapsed on top of her as she lay there moaning and gasping for air.

"Chucky, that was incredible." she said as she struggled out from under me. She came up on top of me and gave me a long kiss. She could feel my raging hard-on pressing between her legs.

"Let's jump in the shower and take care of this hard instrument you are pressing into my backside," she suggested. I agreed and we went to her bathroom and she began running the water in the shower stall. We climbed in and proceeded to wash each other while streams of water ran over us. She turned around and put her hands up on the shower wall, leaning over.

This gave me an inviting rear view of her ready and waiting pussy, and I wasted no time sliding my pulsing member all the way in. Emily moaned in encouragement as I thrust in and out, not caring for anything except my long overdue release. It was not long in coming and I spurted jet after jet of hot sperm into her eager chamber. After a moment or two and some brief kissing, we climbed out of the shower, dried each other off and made preparations to go to our favorite restaurant for dinner.

Over a before-dinner drink, Emily at last told me what she had been waiting to talk to me about. It seems that she has a girl friend at work that looks upon her as a "big sister". Apparently the girl, Nancy by name, has a serious boyfriend that has been pressing her to "go all the way". Nancy wants to, but doesn't know what is involved or what is expected of her. Nancy has no family and was raised by an old aunt who, when any questions involving sex were raised, replied with, "You'll know when the time comes."

Well, the time has come and Nancy feels completely lost with no one to turn to, so she has asked Emily if she and I would undertake her education. Emily told me that she was willing, but she wanted to know what my feelings would be in the matter.

"I don't want to jeopardize anything that we have together," she said with great sincerity, "and I won't mind telling her "no" if that is what you want me to do."

I couldn't believe what I was hearing. Here was my girlfriend offering me a crack at some other chick without a hint of jealousy. I was afraid to appear too eager for her proposal, so I said with feigned reluctance that I would do it if she thought we should, but only if she was really "ok" with it.

Emily got up to phone her friend and we went on in to dinner and had a pleasant, relaxing meal. All through the repast I was wondering about what I had let myself in for. I resigned myself to going through with it even if Nancy turned out to be the ugliest thing I had ever seen.

I stopped by the liquor store on the way back to Emily's place to pick up another bottle of Chardonnay, fearing that the one in the fridge might not be enough. We arrived at the apartment to find Nancy already there and waiting for us to show up.

Emily handled the introductions as we let ourselves in. The girls moved toward the sofa and I broke out the wine and joined them. After a few minutes of small talk, Nancy began to thank us for taking the time to do this favor for her. She reaffirmed her complete lack of experience beyond heavy petting and mentioned that she had been taking birth control measures because she wanted to satisfy the boyfriend and not lose him due to her reluctance even though she was very apprehensive about what might be involved in letting him have his way. Emily must have formulated a plan because she said we should start off by undressing, sharing the wine and my doing some preliminary heavy petting with Nancy. This agreed upon, we each self-consciously took off our clothes.

Nancy was a very attractive young lady just about the same size as Emily, but a brunette with gray eyes. She had trimmed her pubic hair into a small triangular patch with the tip pointing down. Her breasts were larger than Emily's with small nipples that just cried out to be kissed and sucked. We repositioned ourselves on the sofa with Nancy in the middle.

We started with a toast to our adventure and I put my arm around Nancy and pulled her toward me for an initial kiss on her full lips. She opened up willingly for me and I drew her tongue into my mouth and caressed it lovingly with mine. At the same time my free hand was lightly stroking her body from her cute little ears to her belly, bypassing her breasts for the moment. Nancy moved her hand down my body, searching for my awakening tool. When she found it, she gave it a squeeze and began gently stroking it up and down.

This signaled to me that things were rapidly getting serious, so I suggested a move to the bedroom. All three of us left the sofa and moved to the bed where I laid Nancy down on her back. We lay sideways on the bed and Emily and I each positioned ourselves with Nancy again in the middle. I covered Nancy's left breast with my lips and toyed with the nipple, nipping it gently with my teeth. As I avidly licked and suckled the one breast, I allowed my other hand to cup the other and tenderly tweak the nipple with my thumb.

At the same time, Emily was stroking Nancy's arm and asking her if everything was all right. I was wondering in the back of my mind if Emily had a hidden thing for girls and how all this was affecting her, but I was too busy with Nancy to ask or care.

Nancy moved her hand over my stomach and reached for my now fully hard prick again. She measured my length briefly and began to investigate my balls, going so far as to brush over my asshole, causing me to thrust my pelvis upward. I got up from the bed and asked Nancy to scoot down toward the foot of the bed. I knelt on the floor and opened Nancy's legs, giving me a full view of her luscious pussy and the moisture glistening on her thighs. I moved my head down and licked the inside of her quivering thighs from her knees up to her crotch. Unable to hold back any longer I placed my hands under Nancy's perfect ass and, inhaling her fragrant aroma, feverishly licked from her asshole to her clit like a dog lapping up water.

Nancy gave a squeal of passion, began to fondle both of her tits and jammed her mound against my mouth. I released my grip on her butt, spread the lips of her pussy with my thumbs and began a full-time assault on her clit.

Nancy, who had been relatively silent until now, gasped, "Oh, I've never felt anything like this before. Boys have touched me and I've played with myself, but it was never like this. Please keep doing it — take me all the way — PLEASE!!!"

To heighten her excitement, I gently slipped one finger, then two, into her eager vagina and began moving them in and out. I did not encounter any barrier to the full insertion of my fingers into the tunnel of love — something else not to worry about.

Nancy continued moaning with pleasure as my tongue kept working her hooded nub, orally pulling on it and circling it with my tongue. Her orgasm came without any warning. Her moans of pleasure became gasps of pure delight as she pushed my head into the valley between her legs. Her wetness flowed over my fingers as I kept up my attention to her clit and my digital assault on her thrusting pussy.

Her body suddenly tensed, her thighs clutched around my head and she shouted, "Oh YESSS!"

While her body relaxed, I kept up a slow licking of Nancy's fluids, enjoying the musky taste. When I could sense that she had returned to normal, I got up from the floor and went to the bathroom to wash my face. I returned with a warm cloth and a towel and softly cleaned Nancy's soaked genital area. Emily was softly asking Nancy if what had occurred was all that she had expected and if she was ready to go on. Nancy was ecstatic, claiming that the sensations that she had experienced were beyond belief. "I've never cum like that before," she said, "I never knew how good it could feel to have a man go down on me."

She profusely thanked me and Emily for bringing her to the gates of such pleasure. Emily then told her that it was time to continue on with the experience because I had to be relieved of my sexual tensions. I asked Emily how she was faring herself and she confessed that she had brought herself to a climax while I was working on Nancy.

I lay back on the bed with my rigid dick standing proudly above me. Emily told Nancy to straddle my body, facing me, and insert my cock into her pussy. She told Nancy to take her time, that this way Nancy would be in control in case there was any discomfort and she could take as much of my prick inside of her as she wished. Nancy did as she was told and I found myself looking up at her beautiful body and tantalizing breasts with perfect pink nipples. Nancy leaned forward and kissed me. "I know I'll enjoy this and that you will be gentle with me," she said with a smile.

Nancy grabbed my shaft and moved the head of my cock back and forth in her moist slit, coating my prick with her juices. Finally, she positioned my throbbing prick at the entrance to her opening and gently eased herself down on it.

"Here it goes," she said, looking down at my prick entering her pussy. She started her descent and I felt her slick vaginal walls surrounding the head of my dick. "My God, that is the most intense feeling," Nancy exclaimed.

She began slowly moving up and down on my cock. I could feel the walls of her sheath slightly loosening to accommodate the size of my prick. I placed my hands on her hips to steady her gorgeous body as she took in more and more of my pulsating dick.

"Are you doing all right?" Emily asked as she tenderly stroked Nancy's leg. "Oh yes," Nancy groaned, "I can't believe how good this enormous prick feels inside of me." I could only smile at the flattery.

Without another word she began to slowly raise and lower herself. It was the most wonderful sensation as my stiff cock moved ever deeper into her descending pussy. She stopped her up and down motions every once in a while and tensed her vaginal muscles, gently milking my cock as she adjusted to its size. She began again moving up and down, quickening her pace until she finally took in as much of my prick as she could, and then stopped, collapsing on my chest.

"I feel so full, it's... delicious," she said, facing toward Emily who was lying there looking at the both of us with a smile on her face.

We did not move for a few moments as I gently squeezed Nancy's butt, waiting for her next move. She was so wonderfully warm and soft, lying there on top of me. I flexed my cock a couple of times to indicate that I was ready to press on. She raised herself back up and I sucked one of her nipples into my mouth. I suckled gently as I thrust upwards, forcing my pelvis against hers.

"Oh keep sucking me—your cock feels SO good inside of me." She ground herself on my stiff prick with a rotary motion while I stimulated her clit with my thumb. Suddenly Nancy threw her head back and uttered, "Oh my God," she screamed, still moving with intensity against my crotch. "I'm going to — CUM!!'"

With her tit still pressed against my face I could feel Nancy's muscles contracting around my thrusting prick. I kept up my stimulation of her clit as she tensed up and came all over me, flooding my balls and thighs with her flowing juices. Nancy fell against me once again in a state of total relaxation. I was so horny that I couldn't help myself and I grasped her sweet ass and began pumping for my release. I was soon erupting within her, experiencing an incredible orgasm as I shot jets of cum deep inside of her. I was surprised to feel her pussy muscles begin to clamp around me as she tried to increase the pleasure I was deriving from my orgasm. After a few seconds Nancy adjusted her position, allowing my deflating cock to slip out of her pussy and releasing more wetness over me. She rolled off of me and stretched out luxuriously beside me on the bed.

"That was wonderful," she breathed, "it felt better than I had ever imagined, and I don't know how I can ever thank the both of you."

"I'm glad you enjoyed it," Emily replied, "but there is one more lesson to be learned before we are done, if you are up to it. Let's all get cleaned up and have some more wine before we get to it."

After some sponging and primping, we all gathered again on the sofa, still in the nude. I broke out the last bottle of the wine and served all around. As I gazed at my two beauties sitting on the sofa in all their glory, I couldn't believe what had happened to me. Nancy was a gorgeous gal and a great lay even though she lacked experience. Her intended was going to be a lucky guy. My feelings for Emily were not challenged by the encounter with Nancy. I only hoped we could get back to our relationship without any damage from tonight's activities.

The girls had made room for me between them as I settled back down to enjoy the wine I had poured. Emily was telling Nancy that the only thing left was the subject of oral sex known as a blow job — after that, everything else was just a variation. Emily offered to demonstrate on me or let Nancy do me while she told her what to do. Nancy said that she had always wondered what cum tasted like and whether she would be able to swallow it without gagging. Emily said that Nancy should do the job on me in order to erase any doubt from her mind and reminded her that this would be the place to try it if the initial trial did not work out well. That said, Emily told Nancy to reach over and get more familiar with my cock. Nancy did as she was told and grasped my semi-erect prick in her hand. My cock responded to her touch and I could feel myself coming to full erection as she gingerly stroked my shaft up and down.

Emily told her to lick all around my rock hard shaft and then put it in her mouth to become accustomed to the feel of it. Nancy allowed her lips to kiss the tip of my cock. She then, holding my prick in her hand, licked up and down all around the shaft before introducing the head of it into her mouth and gently sucking on it. She reached down with her hand and caressed my balls, lifting them and gently squeezing them.

Emily then told her to take as much of my cock into her mouth and down her throat as she could without gagging or removing her hand from my shaft. After that was done, Emily told her to try swallowing a few times with my cock still in her throat. The sensation of her throat closing around my dick was a wonderful new sensation for me. Emily next told her to swish her tongue around my sensitive cock head. Finally Emily told her to suck gently on my prick while moving her head and her hand up and down and breathing through her nose. Emily then lay back, indicating that Nancy was on her own.