Amy's Anal Introduction - 3 M/F anal oral

[Headcook69]

The following story is a work of fiction. Any resemblance to actual people is purely coincidental. I would like to acknowledge cutegirl3818 for this story. It was her idea and she gave me the inspiration to write it so if you like what is written please send her some praises also.

Amy's Anal Introduction - 3

Well tonight I didn't go through all of the emotions and feelings I did the previous couple of days. Of course I was still nervous and had a little fear about taking his cock in my ass but after what he did to me and how he made me feel earlier today I was comfortable with my decision to go through with this. I still had the fear I wouldn't see him again after tomorrow, more so now because I discovered my feelings for him weren't just sexual ones. He was the perfect man for me and just the type I was looking for. His age didn't even matter to me. I slept pretty soundly that night and couldn't wait for tomorrow to get here. The whole day at work seemed to drag on and on. When I got home I went right to my bedroom to choose my outfit. This time I decided not to wear my bra and panties. I figured I wouldn't need them anyways and they would just be in the way. I chose a plain blue skirt that was about mid thigh and a printed blouse that went well with it. On the drive to his house I had to chuckle at myself. After all here I was all excited to go see a man just to lose my ass virginity.

When he opened the door after I knocked we smiled at each other and he invited me in. We looked into each others eyes momentarily and then I gave him a friendly kiss on the lips. As we looked at each other again I think both of us figured that wasn't enough and seconds later we were locked in a deep, passionate kiss.After we broke that kiss I took matters into my own hands and began to unbutton his shirt.

He chuckled, " I don't need to bribe you with wine this time?"
I giggled as he then began to unbutton my blouse. When he opened it and seen I wasn't wearing my bra he looked at me curiously. I smiled, " I figured my bra and panties would just get in the way."

He laughed, " A girl after my own heart."
We stood there naked, looking each other up and down. I looked at his cock, which was hard as a rock now, and it looked even more beautiful than yesterday. I couldn't help myself as I went slowly to my knees and took hold of it. I began by licking all around the head and then up and down his shaft.
" GGGOOODDD LLLOOORRRDDD" he groaned as I did this.
I then gently took each of his balls into my mouth and gently sucked them. I never really did this with any of my other boyfriends but I loved the way his felt in my mouth. The way he was moaning and groaning I guessed he loved it too. I sucked and licked his balls for a few minutes and then went to work on his shaft again. This time when I got to the gorgeous crown I opened my mouth to suck as much of his cock into my hungry mouth. I took hold of the base and bobbed up and down his cock. I loved the way it felt and tasted in my mouth. I really could suck on this gorgeous piece of manmeat all day but he had other plans. Within a few minutes he took hold of the back of my head, pushing as much of his cock into me as he could then groaned.
" CCCUUUMMMMMMIIINNNGGGGGGGGGGG !!!" and seconds later I felt him swell slightly just before my throat was splashed full of searing hot cum. I greedily swallowed and swallowed as his wonderful balls emptied themselves into my mouth. He came so much that I felt some leaking out of the corners of my mouth. I took all I could down my throat and then sucked some more to make sure every drop was out of him. We kissed as I stood up and again he said, " Yes ma'am, that is definitely one area you don't need coaching in."

I laughed, " I'm glad you like my oral talents Brad."
He then took me by the hand and lead the way to his bedroom. I felt some butterflies, knowing why I was going there, but I was also anxious to feel his cock in my asshole. I never thought I would be this anxious to take a cock into my ass but he made me crave whatever he was going to do to me. I was really falling for Brad hard and those feelings of never seeing him again resurfaced.

This time we got onto hid bed and we kissed awhile as we caressed each others bodies. His powerful hands roaming up and down my body, caressing my tits, my pussy and my ass cheeks sent shivers throughout my entire body and ending up deep inside my love canal. I wanted him so badly I could taste it. After a bit of this he asked me to lie on my stomach. I eagerly did and he began to kiss and lick my neck.
" OOHHH BBRRAADDDDD!!" I moaned as he did this. He then very slowly worked down to my shoulders and back, causing me to arch upwards with the need to feel his hands and tongue on me. He worked on my lower back a long time until I finally couldn't take it anymore, " Please Brad, go lower."
He just chuckled and eventually did go lower. He placed gentle, loving kisses all over my ass cheeks. It felt so amazing to feel his hands and tongue kissing and licking my ass. He then gently opened my ass cheeks and the second I felt his tongue make contact with my asshole I arched high into the air and moaned loudly. I heard him say in a whisper, " MMM such a beautiful, tiny ass."
He spent a lot of time kissing and licking my asshole. He then gently worked his tongue into it and I screamed, " OOOOHHHHH CCCUUUMMMMMMIIINNNGGGGGGG" and my body went into shivers that made my pussy leak onto his bed. I arched high into his mouth as I came. When I calmed some he got off the bed momentarily and as I looked at him he grabbed a tube out of his dresser drawer. I knew it was anal lube of some sort but didn't feel the slightest fear. I now trusted Brad fully and wanted him to take me in the ass.

He got back onto the bed and I laid there awaiting his next move. He gently opened my ass cheeks again and I felt a cooling sensation on my asshole. I knew he was applying a generous amount of the lube. He then kissed and licked me for a bit, then he placed his finger on my asshole and gently pushed. I felt the pressure of his finger on my asshole and then without any pain it slid past my sphincter muscle and into my asshole.
" MMMM OOOOOO BBBRRRAAADDDD" I moaned loudly as he held his finger inside me.I even arched upwards to get more finger into me. He then very gently began to finger my ass. It felt so amazing to me. I moaned and groaned as he did this for awhile. When he removed his finger I actually remember groaning in complaint and saying, " NNOOOO, please don't stop."

I then heard a drawer open and looked over my shoulder. He took some kind of dildo out. It was fat on the end that he held but then it was slim and ribbed where it would go into my asshole. Moments later he was back at my ass and when I felt the dildo touch my asshole I moaned. He applied gentle pressure and it slid into me. I groaned loudly as he sank it deep as it would go into my ass. I arched my hips and he began to move it in and out.

"" OOOHHH GGGGOOODDD SSSOOOOOOO GGGOOOOOOOOODDDDDD!!!"I moaned and groaned as he fucked me with his dildo. After a little while of this he removed it and again I complained. He then reached into the drawer and this time he took out some beads. There were three beads, each one a little bigger than the previous and then the end of it was a fat, round tube that I assumed was going into my asshole too. He kissed my ass some more then I felt the first bead being inserted into me, causing me to arch my hips and moan. He waited a few seconds then inserted the second. It was bigger but still felt good.
" MMMMM OOOHHH BBBRRRAAADDD" I moaned in a whisper as the third one slid into my virgin asshole. I then felt the tip of the tube against my ass and actually arched my hips, wanting it inside me too. He pushed gently and it did hurt a little but the pleasure I was feeling at this point outweighed that pain by far. I grunted as it slid into me but this he left just outside my asshole, causing it to stay pried open. It did feel kind of funny but good at the same time. I actually did feel a little embarrassed too because I knew he could see this thing sticking out of my asshole. The next thing he did to me sent me into orgasm land again. He inserted the other dildo deep into my pussy and began to fuck me with that as my asshole was stretched by the tube in it.

" MMMMM OOOOHHH CCCUUUMMMMMMIIINNNGGGGGGGGGG!!!!! " I yelled out and again flooded his bed with my pussy juices, now pouring out of me like a fountain. He continued fucking my soaked pussy and I came again"GGGGOOOOODDDDDD AAAGGGAAAIIINNNNN!!!" thrusting my hips up and down in a frenzy.

He then let me calm down some and catch my breath. The next thing I felt was his weight on top of me. I knew I would soon feel his cock up my ass and I craved it at this point, more than any other cock that has been inside me. I don't know when he pulled the beads out of me but they were gone. He then reached down and spread my ass cheeks open. I expected to feel his gorgeous cock enter me but instead he just laid it between my cheeks. I groaned in complaint, " NO, please put it in me." but he just kissed my neck and rubbed it up and down the crack of my ass. I arched my hips and begged," God Brad, please fuck my ass. I need it so badly PLEASE FUCK ME!"

He just kept rubbing it up and down the crack and I was so horny and in need of his cock inside me that I was actually getting angry at this point, "  DAMMIT BRAD, PUT YOUR FUCKING COCK INSIDE MY ASSHOLE YOU FUCKER"

He chuckled and seconds later I felt the rubbery head of his cock on my tender asshole. I didn't even wait for him. I quickly thrust my hips up as powerfully as I could and felt a couple inches of the cock I so craved sink into my virgin asshole. I screamed out from the pleasure and came hard. "OOOOHHHH GGGOOODDD CCCUUUMMMMMMIIINNNGGGGGGGGGGG" This time I must have passed out momentarily or something because I don't remember him sinking the rest of the way into me but suddenly he was buried to the hilt in my asshole and I was once again begging him to fuck me.

As he began to pump his wonderful cock in and out of me I could feel the muscle of my ass stretching out even more but there was no pain whatsoever, only the most intense pleasure I have ever felt in my entire life.

" MMMM YYYYEEEESSSSSSSSSSSSSSSSSS, Fuck me ass raw Brad. God I need you so bad, fuck me fuck me fuck me" I said, not caring that I probably sounded like a wanton slut.

Brad did just that too. He kept a nice slow pace for a really long time. Both of us moaned and groaned as he fucked my ass good. After what seemed like an eternity he yelled out, " III"MMM CCCCUUUUMMMMMMMMIIIINNNNGGGGG  AAAAMMMMYYYYYYYY!!!!" and I felt him swell slightly and then " MMMEEEEE TTTTOOOOOOOOOOO" as his hot cum began to pour deep into my asshole. It felt like he shot a gallon of cum inside me before he began to empty out but I wanted more. He collapsed on top of me and we both had a hard time catching our breath from the intensity of our orgasms.

When we recovered enough he got off me and I cuddled against him as we kissed. I then laid my head on his shoulder, wondering if this was over between us now. I looked into his eyes and he smiled at me and kissed me deep again. To me this was a sign that he loved what we just did as much as me. I then smiled and smacked him hard on the chest.

He laughed and asked, " What was that for?"

I giggled, " For making me beg so much for your cock. I have never begged or wanted a cock so much."
We then kissed and I decided to get brave. " Brad, um...... could I ........um........would you mind if I stayed here tonight?"
His response was to smile from ear-to-ear and trace the heart of my pussyhair saying, " well if you do you won't get much sleep."
I giggled, " I was hoping not"
" I am a lot older than you Amy"
Again I giggled, " Does that mean you want me to call you daddy when you are on top of me fucking me?"
He laughed and rolled on top of me, " I think we will get along great Amy honey. "He then lined his cock to my pussyhole and....................... well let's just say I didn't sleep at all that night or any other night I spent there and Brad and I are going to the Fourth of July celebration together.

THE END!

[Headcook69]

The following story is a work of fiction. Any resemblance to actual people is purely coincidental. I would like to acknowledge cutegirl3818 for this story. It was her idea and she gave me the inspiration to write it so if you like what is written please send her some praises also.

Amy's Anal Introduction - 2

When I got back to my apartment I decided to put my new outfit on again to make sure it looked as good on me as it did in the store. As I was posing for myself in front of my full-length mirror I decided it looked superb and was happy. When I turned my head and waist to check out how my ass looked in it the conversation with Nicole came to mind. " Do I really want some strange man fucking me in my ass?  It will hurt, I just know it will, but Nicole did say that Brad was an expert and very good at it. Well Amy, you have been curious about this so here is your chance to satisfy your curiosity once and for all. " I had a million thoughts going through my mind, some why I should do it and some why not to. I was feeling so confused with my emotions. I was nervous, confused, scared, yet in a way I was also excited, hopeful because of way Nicole told me about Brad's expertise. I decided to just go to bed, get a good nights sleep and think on it more tomorrow. It will be clearer to me then.

As I undressed to get ready for bed I looked at myself naked in the mirror again and wondered what Brad would think of me naked. " Why are you even thinking of that Amy" I thought," If you do this Brad will probably never see you again so what difference does it make what he thinks. Besides you are very pretty and have a nice body." But of course like any woman I can point out many flaws with myself and I did.

I had a hard time falling asleep that night and kind of wished that Nicole would never have brought the subject of anal sex up but then remembered I was the one that brought that up. After awhile I drifted off to sleep.

I went to work the next day as usual but my mind kept drifting to anal sex and as I looked at some of my female coworkers I wondered how many of them got fucked in the ass. By the end of the day I had made my decision so I called Nicole to tell her.

" Hi Nicole it's me. Um, could you give me Brad's phone number. I want to call him and meet him for coffee and discuss this." I couldn't  be 100% certain I was going to do this so I thought by meeting Brad in person I would be able to decide, after all he was the one that was going to get my ass cherry and if I didn't like the way he come across then I just wouldn't go through with it.

I very nervously called Brad and we decided to meet at the mall coffee shop and talk. On the way there I had butterflies in my stomach and my nerves were so jumpy. I knew what he would be wearing so I looked for him when I got to the coffee shop and the person I saw was for sure a plus. He was as handsome as Nicole said he was and that made me feel a little better. He had a very handsome face with black hair that was neatly trimmed. He was sitting down but his body looked to be in good shape. He wasn't the muscular type but he also wasn't the slouching type that don't take care of themselves. I slowly walked over to the table he was sitting at.
" Brad?"
He looked at me and smiled, " You must be Amy. Please sit down and I will get you some coffee."

We sat there and talked for awhile and he had the type of voice and manners that really made me feel at ease in his presence. I began to feel better about letting him be the one to teach me anal sex and by the end of our meeting I had his address and was going to meet him there the next night. I was actually going through with this.

As I got ready to go to Brad's the next night of course I had to go through all my clothes to decide what to wear. At one point I even thought about wearing an old baggy pair of sweats I had so it would turn him off but then settled for a nice skirt and blouse with matching blue bra and panties. I was a nervous wreck on the way there and when I went to knock on his door I almost turned and left instead. I knocked and he opened the door with a smile.

" Amy, please come in."
I walked in and looked around a bit. He had a very nice looking place and for a single man it was immaculately clean and orderly. This made me feel a little better about my decision.

" Please sit down."
I sat down and looked at the floor. He sat a little away from me and said, " You look a little flushed, is everything OK?"

I looked at him and blurted out, " You're about to rip my asshole to shreds and make me walk funny for the rest of my life so yea everything is just peachy Brad."  I immediately covered my face with my hands in embarrassment and said, " Oh god Brad, I am sorry. I don't know why I just said that. Please forgive me."

He just laughed and replied, " Don't worry about it Amy, I've heard that response before. Would you like a glass of wine?"

I had to giggle and say, " Oh so now you want to get an underaged girl drunk before you rip her ass apart huh?"

He again laughed, " Under the circumstances I think you can decide if you want to drink even though you are only 19." I said a glass of wine would be nice and he went to get it. We sat there talking for awhile about nothing in particular and I felt myself calming down somewhat. Brad and I actually had a lot more in common than I thought we would and suddenly the fact he was 42 didn't seem to matter. He soon had me laughing and telling some of my more embarrassing moments in life. He also told me some of his.

" Amy, do you like massages?"
" I guess so, I've never really gotten one before."
" Well then, why don't we go to my bedroom and I would be happy to give you one."

I felt the butterflies returning and my nerves got jumpy but I let him take my hand and lead me to his bedroom. He had a huge kingsized bed with matching furniture there and it really looked like a comfortable room. He pointed to a table in one corner and said, " You want to lie down and we'll begin."

I looked at him nervously and asked, " You want me naked?"
He smiled and replied, " Tell you what Amy, why don't you just take your blouse off."

I was surprised by this request but kind of happy too. I slowly unbuttoned my blouse and took it off. I saw him smile as I revealed my blue lacy bra to him but he didn't ogle me like most men do. He looked for a second and then resumed his eye contact.

" Please lie on your stomach Amy."

I did as asked and felt so tense and nervous. When his hands first touched my shoulders I tensed even more and twitched. He started to rub my shoulders and said in a soft, calming voice, " Just try to relax Amy."

As he began to massage me I did feel some tension releasing. He did my shoulders for awhile, moved to my arms and then down my back. His hands felt really strong yet gentle on me and it felt good. He then moved to my legs and took my heels off to massage my feet and toes. At one point I think I even moaned some but can't be sure. I felt myself relax as he massaged. He then moved back up to my shoulders and back. This time as he did my back I felt him undo the clasp of my bra. He massaged a little more and then asked, " Could you turn over for me Amy?"

As I was turning I thought he would just rip my bra from me  and ogle my naked tits because he already undid it but to my surprise he didn't. He again began at my neck and shoulders, massaging lightly and gently. I relaxed more as he did my legs and feet again. When he moved up to my upper body again he rubbed a little and then I felt my bra straps being lowered on my arms. For some reason this felt so natural to me so I lifted my arms some so he could remove it. I kept my eyes closed as it came off, wondering what he thought of my breasts. " Did he like small ones or big ones? Did they look nice to him? God, he don't like them at all!" and other thoughts raced through my mind as he continued his massage of my body. He waited a long time before he actually touched my tits and that was driving me crazy for some reason. I actually wanted him to caress them and he waited. Finally when he did lightly brush a finger over my nipples I let out a long moan. He massaged my nipples and they became rock hard. I was a little embarrassed but pushed that thought quickly away because that was a normal reaction when someone plays with my tits. He then gently took hold of each nipple and rolled them between his fingers causing me to moan out loud and arch my back towards his fingers.

This went on for what seemed like forever and then he went to my lower body again. This time he massaged my legs and went under my skirt and I didn't tense up or twitch at all. His hands felt so natural on me now. When I felt the button and zipper on the side of my skirt being opened I opened my eyes to look at him. He just looked into my eyes and the look was so calming that I lifted my hips so he could remove it. I then watched as he massaged some more and when he gently hooked his fingers into the waistband of my panties I again automatically lifted my hips. When he pulled them down and got his first look at my heartshaped blonde pussy hair he smiled and said, " Home is where the heart is."
I had to laugh and said, " That is what Nicole said when she did that." I still don't know why I told him that but he laughed too.
He massaged me again and this time he came all the way up my legs and rubbed the lips of my pussy. " Oh god that feels so good" I moaned as he rubbed. His massage soon zeroed in on my pussy and within seconds of him touching my clit I screamed out, " OOOHHH GGGOOODD III'MMM CCCUUUMMMMMMIIINNNGGG!!" and that orgasm sent chills throughout my body and was more powerful than any orgasm I've ever had before.

He then asked me to turn over again and when I did I heard him under his breath saying, " Oh dear lord"
" Is something wrong Brad?" I asked.
" Hmm Oh no, nothing."
" Come on Brad tell me. I heard you say that."
He laughed and said, " OK but you must promise never to tell Nicole."
I laughed , " OK I promise."
" Well, when I did this to Nicole I thought she had the best looking ass in the world, that is until now. I must say I have never seen such a gorgeous little ass in my life."
I had to smile at that compliment and replied, " And just think, you will get to fuck mine" and didn't even feel embarrassed about saying that. I was really beginning to feel so comfortable with Brad and was so glad I decided to go through with this. I don't know if this was the way it was suppose to be but he seemed to forget all about the rest of my body at that point and massaged my asscheeks. I moaned as he manipulated them and spread them open, looking directly at my little wrinkled hole with no embarrassment on my part. When his finger made it first rub across my asshole I actually arched my hips up and moaned. It sent electric shocks throughout my body, ending in my pussy, which was soaking wet now. As he rubbed my asshole with his thumb he gently slide what felt like his middle finger into my hot pussy. " OOOHHH GGGOOODDD CCCUUUMMMMMMIIINNNGGG AAAGGGFAAAIIINNNNNN!!!" I screamed out as my hips arched towards him and my body went into convulsions. At this point I really wanted him to just jump on top of me and ram his cock deep into my ass and fuck the shit out of me. He of course had other ideas.

The next thing I felt was a cooling sensation on my asshole. I assumed he had put some kind of lubricant on it and then he was massaging again with his thumb. I moaned, still breathing hard from that powerful orgasm. He did this a bit and then I felt the tip of one of his fingers on my hole. He pushed forward gentle and I groaned as the pressure against my asshole tightened. I then let out a groan as that finger made enough pressure that it slid past my sphincter muscle and entered my asshole.
" OOOHHHH NNNNN OH GOD!" I groaned as he sank it deeper and began to pump in and out. The feeling was so amazing. There was no pain whatsoever and I arched my hips up again. Then he pushed another finger into my pussy at the same time and the rockets went off again,                           " YYYYEEEEESSSSSS CCCUUUMMMMMMIIINNNGGGGGG!!!" I screamed out and this time I think I momentarily passed out from the power of this orgasm. It was so intense.

After I had calmed down and returned to earth Brad had his hand resting on my asscheeks. He gently patted them and said, " I am going to stop there for today Amy. I want you to go home and decide for sure if you want to continue and if you come back I will go the rest of the way."

I was actually disappointed, " But Brad, I do want you to go all the way."
" I have heard that before and then they regretted it so now I do it this way."
I looked at him sadly because I really wanted him to continue but reluctantly got up. He helped me off the table and I looked at him in a playful way and asked, " Well can I at least see what you will be sticking up my ass. It might help me to decide."
He laughed and undid his zipper. When he took his cock out my mouth fell open. Nicole was right, he had a gorgeous looking cock. It was about 7 inches long and the mushroom head wasn't too big but fit the rest perfectly. It was obvious he trimmed his pubic hair and his balls were nice and smooth. It was hard as a rock and I clearly saw the blue veins running up and down the shaft with the larger vein under it where his juicy cum shoots out. I couldn't help myself, I reached out, took hold of it and said, " I can't too well leave you in this condition now can I?" and then I started going to my knees.
" You don't have to do that Amy." he said as I licked his crown.
I looked up at him with my blue eyes and said in a snicker, " I know that" and then took his cock deep into my mouth.

" OOOHHH DDDEEEAAARRR LLLOOIORRRDDD" he groaned as I bobbed up and down his shaft. I worked on his cock and balls, taking each one gently into my hungry mouth, licking and sucking on this gorgeous cock for all I was worth. He moaned and groaned the entire time while gently holding the back of my head. A little later he yelled out, " III'MMMM GGGOOONNNNNNAAA CCCUUUMM!" and seconds later I felt his shaft swell in my mouth. I anxiously awaited and surely wasn't disappointed by the hot load of cum that was shot into my mouth. It tasted so good and I eagerly swallowed every last drop, sucking more to make sure he was empty. I stood up and we kissed.
" Well, that is one area where you definitely don't need teaching Amy."
I smiled and kissed him again, " Well thank you Brad."
I then got dressed, leaving him my bra and panties because he asked for them. I left shortly after that, already knowing I would be returning the next night. Once I got home I started going through the emotions that I probably wouldn't be seeing Brad after tomorrow and that really made me sad. I was really beginning to have intimate feelings for Brad, despite our age difference. I had never met a man like him and not being with him saddened me. Later on Nicole called me to see how things went. I told her all about it and also how disappointed I was when he stopped. She laughed and said she felt the same way when he did it to her. She said her and Sam got home and she practically raped him that night she was so horny. I laughed and told her my dildo would definitely get a workout tonight. I think she sensed how I was feeling about Brad but didn't say anything.  I then went to bed and really gave my dildo and pussy a good workout before finally being satisfied enough to go to sleep.

[Headcook69]

The following story is a work of fiction. Any resemblance to actual people is purely coincidental. I would like to acknowledge cutegirl3818 for this story. It was her idea and she gave me the inspiration to write it so if you like what is written please send her some praises also.

Amy's Anal Introduction

Today is a beautiful summer day. The sun is shining brightly, birds are chirpping, and I can see the kids in my neighborhood playing, laughing and having a good time. I really love to lay out in the backyard on days like this in my tiny bikini and catch some rays but today I couldn't. There was a dance coming up at one of the local halls and I wanted to buy a new dress for it. It is the Fourth of July soon and they have this big celebration every year that has a dance and ends in fireworks. I usually go with a boyfriend but I am currently not dating anyone. It isn't because I can't find a man or that I am ugly because I have been told by a lot of guys that I am a knockout. The reason is because the types of guys that are asking me out only want to get into my panties because of a nasty rumor one guy spread around about me after we broke up and at 19 I am looking for someone that wants to be with me for who I am, not just to get me in bed. I really love having sex don't get me wrong, but right now I feel that I need more than a still cock inside me for a few minutes and then he cums, leaving me hanging. I live in a medium sized town of 65,000 people so I think I should be able to find at least one guy that doesn't want to just fuck me so that is why I am going to this dance.

I wasn't sure what I was going to buy yet but I thought about a nice skirt and blouse set. I didn't want the skirt too short but I didn't want it too long either. I wanted to send the message that I was available but not one of being easy. I also planned on getting a really sexy bra and panty set. I figured if a guy does get lucky enough to get my outer clothes off me he should be able to look at something sexy before stripping me of those too.

I parked in the mall parking lot and started walking around looking in shops. I saw some nice looking outfits but nothing that I really wanted. As I was heading for another store I heard my name being called out from behind me. I turned to see who it was and my face lit up. It was my best friend Nicole. Her and I have been really close since the beginning of High School but haven't seen each other in awhile. Our work schedules clashed and she has a boyfriend named Sam that she spends a lot of time with. They have been dating for a couple years now and are talking marriage the last I knew. I was really happy for her because Sam always seemed like a nice guy every time I talked with him. I was also a little jealous because I couldn't find a nice guy like him.

" OH MY GOD NICOLE!!" I yelled out as I ran to  greet her.
We gave each other a big hug and friendly kiss. I should mention that I was also a little jealous of her because of her looks too. I am pretty but she is just gorgeous in my mind. I stand 5'4" tall and weigh 106 pounds. Guys tell me I have a pretty face. My body is slim and my breasts are 34b. I work out to keep my flat stomach and my legs are slim and pretty nice looking if I do say so myself. I have noticed a lot of guys, and some girls turning when I pass to check out my small ass and that always makes me smile.

Nicole on the other hand is 5'6" tall, weighs about the same as me and her face is so beautiful it looks like a sculptor did it. Her chest is perfect at 36c. She can eat like a horse and never gain an ounce.Her curves and hips are to die for and I think her legs are her best asset. While my hair is straight blonde she has really naturally wavy jet black hair that goes down to the tiniest ass I ever saw on anyone. She was so beautiful that I wanted to fuck her and I am a girl for Christ sakes. I always was envious of her. Her and I did actually fool around some when we were younger like I think any best friends do. She is the one that trimmed my pussy hair. We were in her bedroom one day changing to go someplace and when she took her panties off I noticed that she shaved her pussy hair off completely. She giggled and said it felt good. I really liked the way it looked so I asked her to shave mine too. She agreed but when she was done it was all gone except the shape of a heart above my slit. She giggled and said it looked so cute that way that I left it and have had it that way ever since.

" My goodness Amy, what have you been up to?" she asked.
" Let's go get some coffee and catch up Nicole."
" OK, sounds good." So off we went to the coffee shop in the mall. We talked about work and other things we had been up to lately. Nicole and Sam had set a wedding date and she asked me to be her maid-of-honor, which of course I eagerly accepted. About half an hour into our conversation Nicole giggled and said," Amy, seeing as you aren't dating anyone, why don't you look up Stanley Westinghouse."

I smacked her arm, " GOD NO!" Stanley was my first real boyfriend and the one that got my virginity. He was terrible in bed, you know the type, a couple pumps and a squirt and he was done, leaving me hanging. At first I figured it was because of his inexperience, and mine too, but as time went on it didn't get better and he was bragging to his friends about fucking me so we broke up. After that I got asked out all the time and I did actually date a few that I allowed to remove my little panties and they were good in bed but emotionally they turned out to be immature so they didn't last.

" So, what about Sam? Is the sex with him still good?" I asked her giggling.
" Yes it is still good, even better now" she said with a blush then went on to say, " We did something about a month ago that was really good."
I waited for her to continue but she hesitated. " Well what was it girl, don't leave me in suspense."

She laughed, " Well Sam and I were talking about things we would like to try in bed and he said he wanted us to try a threesome with another guy. I blew it off at first and then last month we were at a party and got a little drunk. Well Sam brought up the subject again and I said I wasn't comfortable doing that with someone we knew. Sam laughed, said he had to get a drink and when he came back some guy I never met was with him. I blushed knowing what Sam had in mind but on the other hand I was kinda turned on too because this guy was really handsome. We talked some and then ended up going back to our place with this guy. I was so nervous at first but with the amount of alcohol in me I soon calmed down and soon we were all naked in our bedroom."

Then she stopped, " Well damn girl, don't stop there."

Nicole laughed, " Amy you wouldn't believe how big this guys cock was and could he ever use it. Sam was the first to fuck me and I sucked on the other guy while he played with my tits. His cock barely fit into my mouth but GOD did it taste good. I could have sucked him off all night and swallowed every drop of cum he could shoot but he had other ideas. After Sam came inside me he got on me and when he worked that monster into me I was one constant orgasm as he pumped in and out. He shot four huge loads into me and Sam came in me twice before we drifted off to sleep. The next morning when I woke up Sam was in the shower and the other guy was asleep next to me. I looked down at his soft monster cock and smiled as I went south and began to suck it. He woke up smiling and soon had it buried deep inside me again. Sam came out of the shower and saw us fucking. I think he got a little mad but didn't say anything.  I didn't care, I needed this cock in  me. The guy left after filling me up again and do you know to this day I can't even remember his name."

I busted out laughing, " NICOLE!! You little slut."  We both laughed. We went on to talk about some of our other sexual exploits and then about some things we always wanted to try but never have. Nicole told me she wanted to try a threesome with another woman and see if it was as good as with a guy but was afraid to ask anyone. I just smiled, knowing if she asked me I would do it in a heartbeat, not so much to let Sam fuck me, but to be with her again. Secretly I missed our little games we use to play. I thought about one thing I always wanted to try but was too scared to. I was interested in anal sex for some reason and heard that if it is done right it was fantastic but then others have said how painful having a cock shoved up your ass was so I was reluctant to let anyone do it when they asked.

" I've always wanted to try anal sex" I finally said in a soft and shy voice. I could feel myself turning red from embarrassment just saying that, even to my best friend.

" Sam and I tried that because he really wanted to and it was horrible. He was in such a rush to stick his cock into me that he barely did any foreplay. When he first put his finger in there it hurt like hell because he was too rough and it just felt so uncomfortable having something going in my ass. He did try to stick his cock in but was in a hurry for that too and after I couldn't take the pain anymore I made him pull out. I told him I would never do that again."

" Did it hurt that much?"
" That time it did. Sam felt really bad that I didn't like it and I felt bad because I do love him and want to please him so I decided to do some online research on anal sex. As it turns out, there is a special way it has to be done so both people enjoy it and even better there is a man here in the city that teaches anal sex to females and couples willing to give it a try but are too afraid. His name is Brad and he is a professor at the college. He teaches some courses in therapy but does this on the side."

 Well Nicole definitely had my attention now and I listened all ears as she went on.

" I told Sam about what I had found and after talking about it some he said he would look this guy up and see what he says if I would be interested. He did look him up and I agreed to meet with him to see what he said. I was still scared and hesitant because of Sam and my first try at it but Brad had a way of talking that calmed people. I finally agreed to see him and let me tell you Amy, anal sex never felt so good after he showed us how to do it right. Now whenever Sam wants my ass I bend right over to offer it and sometimes I even initiate it."

I laughed and so did she, " What did he do to you?" I asked her, my interest definitely peaked now.
" I won't go into too many details just in case you want to do it because I don't want to ruin the feelings and emotions involved with it but I will tell you that Brad is a pretty handsome man and definitely knows how to please a woman. He was so gentle and caring during the process and whatever he did to my ass, pussy or whatever he would then have Sam do it to me, instructing him as he went on. I guess I should mention that I hope you like sex toys because you will have a lot of different one inside you before he actually penetrates you with his cock. Did I mention he has a very nice one too." then she giggled, " and you are single right now Amy."

I blushed, " Stop it, he's probably an old man."
She laughed, " He is actually only  in his 40's and as I said,HANDSOME"
" Did yous do a threesome?" I asked, really interested but still leery and frightened now.
" He didn't actually penetrate me anally or vaginally because Sam and I are a couple but if you decide to do it he will you......and he has a very nice sized cock Amy girl."
Again I blushed and was thinking.
" I have his phone number if you want to go see him" Nicole said.
" Let me think about it and I will get back to you."
I looked at my watch and had to get going to get my outfit so we said our goodbyes and I promised to think about this and get back to her.

[IdleBoast]

Oh, that was a good set of stories, thank you!