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ddn2003 Member Since October 19, 2009

A Night Of Firsts

ddn2003 on Virgin Stories

Life was good.  I had just turned the big 3-0.  I finally had a great job, a place of my own, great friends and an amazing girlfriend.  I still don’t know how I got Allison.  She’s an elementary school French teacher.  We met in her class.  I was invited by the vice-principal to talk to the French classes about my hometown of Montreal.  We went to lunch and seemed to hit it off.  I guess she looked past my physical features and saw the real me.  I’m 6 feet, 300 pounds, steadily losing the weight, but still a big guy.  Ally, on the other hand, is 5’4”, gorgeous with beautiful full breasts.  Guys hit on her all the time, thinking I’m the male best
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friend.  As much as I want to stand up and say or do something, she won’t let me.  She just politely declines their advances, saying that she’s out with her boyfriend.  Ally is truly amazing!

We made around a bit, but we were both conservative people.  I had been with a few other girls before, but Ally had admitted to being a virgin.  She told me that she was waiting for her “one and only”.  I could respect that.  Ally being very conservative, we never got naked or even semi-naked, but our hands would stray under each others clothes.  We didn’t get to be alone that much.  Her father made sure of that.

Her father was a little bit controlling.  Even at 25, Ally went with it.  She was still a daddy’s girl.  She still lived at home, having just started her teaching career.  The most insane thing was that even at her age, she still had a curfew and wasn’t allowed to stay over at my place ever!  It was almost like he didn’t like or trust me at all.  I know I’m a man, but I was and still am, a very respectful and conservative person.

My girlfriend and I had just celebrated our one year anniversary on Thursday.  I showed up at her parents’ house in a nice suit with a single rose, to mark our one year together.  I took her to a fancy restaurant.  We sat in a private area on the patio, where the string quartet played her favourite songs and melodies.  She even got them to play one of my favourites.  Who knew they knew Metallica!  For those who want to know, my favourite is Fade to Black.  We ended the night with a stroll on the Toronto harbourfront, looking out at waves.  I know, I know!  What can I say?  I’m a romantic.

Two days later, we were hanging at my place with our friends.  There was my best friend, Mike, his fiancée Rebecca, Hillary, an ex-girlfriend turned close friend, her husband Will, Ally’s friend Paul, his high school sweetheart Trish, Ally’s best friend Lyndsey and her boy toy of the week.  I forget his name.  While we were all in committed relationships, Lyndsey was slutty to say the least.  She always had a new boy toy almost every week.  We had fun watching a couple movies.  At least, most of us were.  Lyndsey was making out with her boy toy.  We played some games and drank lots of alcohol!

It was getting late and everyone started to leave.  Allison was looking tired and kind of drunk.  Since she drove over, I wasn’t about to let her drive home.  I offer to drive her home, knowing that her dad would be super pissed if she didn’t come home, but we couldn’t even make it to the door without her passing out.  I took her back to the sofa, grabbed her phone from her purse and called her parents.  Luckily, I got her mom.  Thank God her mom liked me!  I explained the situation and told her that Allison was going to sleep in my room and I was going to take the hide-a-bed.  Her mom knew that her husband was not going to be happy, so she didn’t say anything.  Once again, Thank God!

I picked Allison up and carried her to my room.  I gently put her down on the bed.  She sat up.  She wasn’t even drunk or tired.  She staged the whole thing so she could stay the night!  She knew I would NEVER cross her father, so she and Lyndsey planned the whole thing.  Wow!  I never knew she had it in her!  I wasn’t sure what to make of the situation.  She got up and kissed me.  Her kisses always seemed to make me forget about everything else.  She grabbed her purse and pulled out a small bag.  I had noticed it earlier.  Ally told me that she and Lyndsey had picked out something special for the night.

Ally told me to get into bed and went to the bathroom to change.  About five minutes later, she came back to the bedroom and I nearly fell out of the bed!  Allison stood there wearing a see-through black lace bra, matching thong panties and garter belt with shear black stockings!  In the back of my mind, I knew I had to thank Lyndsey for being so slutty!  I think she was waiting for me to say something.  The only thing I was able to mutter was “WOW!  You look… WOW!”  She walked over to the bed.  I was so distracted by her that I didn’t notice she pulled the sheets off me.  I was lying there in only my underwear.  She grabbed my crotch and said “You’re so predictable!  I love that about you!”

I finally was coming out of my daze.  Ally was trying to take off my underwear.  Still being the guy I am, I said “Before we go there, you’re a little overdressed.  Come lay down first.”  She got on the bed.  I unclipped the stocking on her right leg and slowly rolled it off.  I kissed her leg all the way to her inner thigh.  This was the closest my face had ever come to her pussy.  I repeated the process with her left leg and removed the garter belt too.  She must have liked it, because she let out a little moan.

I moved up between her legs and looking her in the eyes said “I love you” and french kissed her.  I rolled us over, so she was on top of me.  I looked up at this goddess on me.  Ally leaned down and we started kissing again.  After a few minutes of making out, I reach behind her and unclasped her bra and she responded by breaking the kiss to remove it.  I had fondled her breast before, but this was another first for us.  She had toonie ($2 Canadian coin) areolas and perfectly erect nipples.  I took them in my hands and started messaging them.  Ally was moaning softly.  I pulled her right breast to my mouth.  I randomly alternated between sucking her nipple, gently biting it and taking as much as I could in my mouth.  I would repeat this on her left breast.  She was now moaning loudly and saying how much she liked it   I continued for a few minutes before she raised up.

She pulled the drawstring on each side of her panties and pulled them off.  Ally waved them in front of my face before throwing them on the floor.  There was a definite and distinct odour!  She looked down at me and asked “Now who’s overdressed?”  She got off me and tugged at my underwear until they were off and on the floor.  We were now both naked.  By this time I was so hard that my dick was pointing straight up.  I’m not huge.  I’m a decent 6 inches, but thick.  “Oooooo!” was all she said before grabbing my dick with her petite hand and stroking it slowly.  I put my head back on the pillow, closed my eyes, enjoying the handjob.

Not more than a minute later, I felt something hot and wet wrap around my dick.  I looked down to see my goddess girlfriend sucking my dick!  What a sight!  What an amazing feeling!  It had been more than a year since a girl had given me a blowjob and Allison was doing a much better job!  I knew she must have learned from Lyndsey.  I really needed to thank Lyndsey!  Ally looked up at me while sucking on the head.  I smiled at her.  She smiled devilishly back and picked up the pace.  I told Allison that I was close to cumming, but that only seemed to make her more determined.  I felt my balls tighten up and warned her again.  Not two seconds later, I came hard in her mouth.  She did her best to take it all.  She cleaned off my dick and asked “How was that?  Was I good?”  My only response was shaking my head up and down.

I recovered my senses.  Allison told me that she had done that once to an old boyfriend, but she broke up with him because he tried to push her to do more than she wanted to.  That was the last time she ever went that far, until now.  I grabbed her hand and pulled her close to me.  We started kissing again.  My hand strayed down between her legs.  She was very wet.  I started rubbing her clit.  She moved her right leg on top on my legs to give me better access.  I started dipping my fingers into her pussy.  She was really tight.  I felt her hymen and stopped there.  I didn’t want to break it.

I broke our kissing and moved my mouth to her right breast.  Allison was breathing heavily and started rocking her hips to the rhythm.  She tried to say something.  All I made out was “Cu……mng”.  And with that, her pussy clamped down on my fingers.  When she stopped cumming, I got between her legs.  I began kissing her from her lips down her body.  I kissed all the way to her pussy.  I looked up and she gave the sign to continue.  I started eating her out.  From time to time, I would push my tongue in her pussy as far as possible or suck on her clit. She was moaning loudly and shifting a little.  I happily continued.

A few minutes later, she locked her legs tightly around my head.  From her moaning and actions, I knew Ally was going to orgasm soon, so I doubled my efforts.  I continued for another minute or two before she went stiff and starting to cum.  A rush of her cum splashed my face.  I just continued.  Just as she was coming down from her orgasm, another hit her harder.  Once again, I just continued.  My previous girlfriends always said if nothing else, I was best pussy eater they ever had!  I stopped after her 3rd orgasm (4th of the night!).  I began retracing my kisses back up to her lips, taking extra time on her breasts.

I was hard again and Allison could feel my dick pressing against her pussy.  She stopped kissing me, looked me in the eyes and said “Take me.”  I was happy we got this far, but I remembered her saying that she was waiting for her “one and only”.  To her that meant marriage.  I asked her if she was sure about that.  She responded with “I love you Dan!  I know you are my one and only.”  My conservative mind kicked in again.  I said “I love you too, but are you really sure you want to do this?”  “100%” was her answer.  Not having any condoms (never thought this would actually happen), I asked her if she was on the pill.  She said yes.  I raised myself up and grabbed my dick.  I lined it up with her pussy and slowly started to push in.  Even with all the lubrication, she was still incredibly tight.  I got the head in and just stayed there for a minute.  I looked down at her.  She was so beautiful.  I’m still not sure what she saw in a shlub like me, but that’s a different story.

I started moving in and out in a steady rhythm, each time pushing a little bit further in.  I reached her hymen and stopped again.  Last chance to save her virginity.  I looked deep into her eyes.  Ally shook her head up and down.  I started the rhythm again, pushing against her hymen.  After a few strokes, I pushed through and was all the in.  She was grimacing in pain and tears were dripping down her face.  I leaned down, kissed her and said “The worst is over.  Tell me when you want me to continue.”  A couple minutes later, she looked up and told me to continue.  I pulled all the way out, until only the tip of my head was in and slowly pushed all the way back in.  She commented on feeling so full and how this was the first time anything was in her pussy.  She never even used a dildo.  Like I said before, Allison was very conservative.

I continued my rhythm and started to pick up the pace with each stroke.  She started to move her hips to my rhythm.  Allison was again breathing heavily and moaning.  We had been going for some time.  Must have been at least 20 or 30 minutes.  She was loving it!  I was loving it!  She came at least a couple more times, maybe more.  After the last orgasm, I was ready to cum.  I again asked if she wanted me to pull out.  She shook her head no.  A few strokes later, I pushed deep inside her and came hard.  Spurt after spurt after spurt.  It felt like forever!  I pulled out and rolled off her.  Cum was dripping out her pussy.  Allison cuddled up to me and said “Thank you.  That was amazing!”  Being her first time, she was a little sore.  It was understandable.  We fell asleep cuddled together.

The next morning, I awoke to a new, yet familiar sensation.  Allison was back at it, giving me a blowjob!  Had she gone from conservative to nymph?  She noticed that I was awake.  She took her mouth off my dick and said “Ah… I’m glad you’re awake!  Ready for more?”  I answered “Of course.  What do you have in mind?”  Allison crawled up and straddled my waist.  She leaned down and kissed me.  My dick was right at her pussy.  She just pushed back and impaled herself on it.  “My turn!”  I didn’t have any objections.  She started to move up and down, slowly at first.  As we got more and more into it, I started playing with her nipples.  She was going faster and faster, as if it was the end of the world.

Ally started to cum.  Her orgasm put me other the top.  I started cumming in her again!  She got off quickly and tried to get as much as possible in her mouth.  She started licking the rest off me.  When Ally was finished, I slapped her ass and told her to go shower.  Too bad my shower was small.  Not enough room for the two of us.  We both showered and got dressed.  We drove back to her parents’ house in separate cars.  I wasn’t about to let her take her father’s tirade.  I was prepared to take the brunt of it.  Boy was I in for it!

When we got there, her dad was mad.  He demanded that I talk with him in his study.  He asked me what happened.  I repeated the story.  She was too tired and drunk.  She slept in my bed and I slept on the hide-a-bed.  I assured him nothing happened.  I wouldn’t take advantage of his daughter in the state she was in.  I loved her.  He accepted what I told him.  As he was about to usher me out, I told him that I had something to ask him.  He invited me to sit down.  He said “What’s on you’re mind?”  I told him that Allison and I had been dating for a year.  We love each other very much.  I proceeded to ask him for permission to marry his daughter.

He just sat there… silent.  For an outspoken man, the silence was eerie.  After an agonizing minute or two, he finally responded with “If she says yes, I will give you my blessing.”  As we got up and headed to the door, he said “Ever since I met you, I was always wondering if you had the balls to ask me that!”  He was suddenly a different man.  He was… nice to me!  Was kind of creepy, but he was being nice to me.  I wasn’t going to look a gift horse in the mouth!

We walked back to the living room, where Ally, her mom and sisters (one older, one younger) were sitting.  Allison got up and asked if everything was ok.  I told her yes and that I had some things to do today.  She was relieved.  I kissed her and told her that I’d call her later.  When I got to my car, I grabbed my phone and called Mike and Hillary.  I told them I needed their help and asked if I could pick them up.  Being my two closest friends, they of course said yes.  They were curious what I needed help with.  I told them ring shopping.

Cooking For Danielle

ddn2003 on Sex Stories

A friend of mine introduced me to Danielle.  After a few dates, I knew I had lucked out.  She was smart, intelligent, funny, compassionate shared the same interests and of course, beautiful! Dannie, as I called her, was  5’4” with flowing red hair and engaging green eyes.  She wasn’t skinny, but wasn’t fat either.  I guess you could say she had a little extra padding.  I’m six feet and had recently lost 140 pounds.

I invited her to my place to show her my culinary skills.  Apparently, women like a man who can cook!  She told me to surprise her for dinner.  Around 7ish, the intercom rang.

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nt size="2" face="arial,helvetica,sans-serif">“Hello?”
“Hi Dan!  It’s me!”  She said.
“Me who?”
“Very funny!  Buzz me please.”  About five minutes, I had a knock on my door.
“Salut!”
“Hi to you too!”  She responded.

She came in and put down her purse.  I hung up her coat and snuck a peek at her ample cleavage!  She was wearing red V-neck short sleeve shirt and a black skirt that accentuated her legs.
 
“Welcome to my place!”
“Thank you for inviting me over.”

We walked into my living/dining room.  I had done my best to impress her.  I had the lights dimmed and candles lit on the table.

“You sure know how to impress a lady!”  She commented.
“Well, thank you milady!”  I said as I bowed... and stole another peek of her cleavage.
“Dinner should be ready in about five minutes.  Would milady care to sit?”  I asked as I pulled the chair out.
“OOOO!  A gentleman too!  Extra points for you!”
“I wasn’t aware there were points!  What are the points good for?”
“You’ll find out eventually! So what has the chef prepared for us tonight?”
“You’ll find out soon enough!”

We started with salad, followed by chicken parmesan with spaghetti and garlic bread.  We drank lots of wine too.  For dessert, I made tiramisu.

“Dan, you are an amazing cook!”  She said.
“Thanks!  I only cook for special people.  Why don’t we grab our wine and head to the couch.”
“Sounds like a plan!”

We headed to the couch where we drank more wine while we talked.  After finishing off a second bottle of wine, Dannie was a little buzzed.

“Dan, can I ask you a question?”
“Of course Dannie.”
“Did you invite me over here for sex?”
“Wow!  I’ll be honest.  I did think about it, but it’s not the reason I invited you over.”
“Really?”
“Really!  I like you a lot and I’m very attracted to you, but sex is never a requirement.”

She leaned over and kissed me on the lips.  We started to make out.  Thinking that I was taking advantage of her, I asked,

“I feel like I’m taking advantage of you”
“You’re not.  The question was a little test.  Most of the guys I’ve dated just want sex when they invite me over.  So I ask the question.  If they say yes or they push for it, I leave.”  She explained.

We went back to making out.  She pulled up her skirt a little and straddled me.  Her breasts were now right in front of me!  What a sight!  I looked into her eyes and saw pure lust!  She leaned down and we began kissing again.  She started dry humping me.  Slid my hands under her shirt and began fondling her breasts.  This went on for 10 minutes or so before she got off me.

“Let’s move this to your bedroom.”  She said.  I wasn’t about to say no!

We continued making out all the way to my room.  As I backed up, I hit the edge of my bed and fell onto it, pulling her with me.  She got up and pulled her shirt other her head to reveal her huge breasts encased in a red bra.

“I know you like these, don’t you?”  Pointing at her breasts.
“Hell Yeah!”

She continued undressing by removing her skirt, letting it fall to the floor.  She wasn’t wearing any panties!  She was gorgeous!  I tried to remove my shirt.

“Here, let me help you.”

She walked up to me, got down on her knees, undid my pants and pulled them off.  She looked at the bulge in my underwear and said,

“Is that because of little old me?”

I just smiled and winked!  She pulled my underwear off, gave my cock a couple strokes and began sucking the head like there was no tomorrow!

Looking down at her, I said “Oh!  That feels so amazing!”

She looked up at me, smiled and began deepthroating my entire cock!  Her small mouth fit my thick cock almost perfectly!  I wasn’t sure how much longer I was going to last.  I kept fighting off my orgasms and she kept trying to induce one.  I couldn’t fight it anymore!

“I’m going to cum!”  I said.

This only made her increase the suction.  I came deep in her throat.

“Holy moly!  That was the best ever!”  I said.

I moved myself fully onto the bed.  Dannie climbed on top of me.  She started grinding her pussy on my cock.  Dannie suddenly stopped and sat up.  I looked at her inquisitively.  She reached back and removed her bra, letting the breasts I’ve been dying to see hang free.

“I know you’ve snuck peeks at them!  Now you don’t have to sneak around!”

I reached up and grabbed a handful in each hand.  They felt so good!

“MMMM!  Pinch and twist my nipples!”  I complied.
“Harder!”  I complied again.

I pulled her down, kiss and then bit each nipple.

“OH!  You dirty boy!”
“You know you like it!”  I said as I winked.
“I certainly do!”

She leaned down and kissed me.  I took the opportunity to roll over so she was below me.

“I wanna fuck you so badly!”  I said.
“Before you fuck me, you’re gonna have to eat me out first!  It’s only fair!”
“No problemo!  Move up a little.”

I lowered my face to her plump pink pussy.  The smell was intoxicating!  I began licking her pussy from bottom to top, swirling my tongue around her clit.

“MMMM!  That feels good!  Keep going!”

I did as I was told!  I mixed it up a little, changing directions and styles.

“Keep going!  I’m close!  So close!”

I applied a little pressure to her clit with my teeth, which set her off into a very loud orgasm.  She was panting heavily as she said,

“Damn!  You’re pretty good yourself!”
“You have an exquisite pussy!”

I moved back up and kissed her.  I reach into my night table for a condom.

 “Is that a latex condom?  Don’t use it, I’m allergic to latex.  Don’t worry, I’m on the pill and I was recently tested”
“Ok.  Not a fan of condoms anyways.”

I grabbed my cock and teased her clit with the tip of my cock a little bit.  I then pushed the head of my cock into her pussy and pulled out.

“Stop teasing me and fuck me!”

Once again, I did as I was told.  I slowly pushed my cock into her tight, wet pussy.  It was a sensational feeling!  I was fucking her with slow and long strokes.  She was moaning with every stroke.  I sped up the pace, which brought a pleasurable smile to her face.  As the pace quickened, she wrapped her legs around me.

“I love your cock in my pussy!  MMMMM!”

As amazing as her pussy was, I couldn’t forget the sight of her on top of me with her tits free from her bra.  I pulled out, rolled off her and told her to get back on top of me.  I watched as my cock disappeared again in her pussy.  I looked up to the familiar sight with a smile.

“Should I just sit on your cock while you admire my tits?  Or should we get back to fucking?”
“I’m done admiring them... for now!”

She gave me a devilish smile.  She slammed down on my cock and continued fucking me hard.  I grabbed her hips to slow the tempo just a bit and matched it with my upstrokes.  We were going at for some time when she said,

“I’m gonna cum soon!”

I increased my upstrokes and put my finger into her ass.  That set her off!  Her pussy locked down on my cock and she was screaming.  A minute or two later, she released her grip on my cock.

“That was better than the first orgasm!  Now it’s your turn!  How can I make you cum again?”
“Let me titty fuck you!”
“You really are a dirty boy!  I love it!”

She caught her breath and rolled off.  I straddled her stomach and put my cock between her huge tits.  She pushed them together and I started fucking her tits.  It wasn’t the same as her pussy, but it was still pretty damn good!  It wasn’t going to take long for me to cum.

“I’m close!  Where do you want it?”
“All over my face!”

I pulled my cock out from between her tits and got up on my knees.  After a very brief handjob, I came all over her face.  As I finished spurting, Dannie pulled my cock into her mouth, sucked the last of my cum out and cleaned off my cock.  I got off her.

“That was awesome!  I’m gonna go wash up.”

I just layed on my bed, revisiting the events of the night in my mind.  A moment later, Dannie returned.  She got on the bed and cuddle close to me.

“Dan, I have to admit that I was hesitant about coming here.”
“Really?  Why?”
“As nice as you have been, I told you about my past experiences and wasn’t sure if you were just being to get me in bed.”
“And now?”
“I’m really glad I ‘came’ over!”
“Haha!  Very cute!”

We cuddled and talked some more until we fell asleep.

Finding a New Fuck Buddy

ddn2003 on Sex Stories

I had a great fuck buddy for almost a year.  She was great in bed and always horny.  One day she called me to say that she had met a guy and they were dating, so no more fun for us.  After a month of frustration, I decided to try one of those adult websites.  I was amazed at how explicit some of these women were!  I sent out a few emails to some of the women I was attracted to and thought I could have some fun with.

I got an email back from JeSsIcA1986.  She said she would be delighted to meet up for fun, but wanted to meet up for somewhere public first so she could get to know me a little bit.  We met up for dinner and drinks at a local pub.  When we met up, I thought I saw an angel!  She was 5’5” with brown hair and brown eyes.&

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nbsp; He was a big girl, but not huge and oh so sexy!  As we were talking, it became apparent that we had a lot of common sexual interests and it didn’t hurt that she lived down the street from me!  We continued talking and until 1am that night.  On our way out she said,

“I would definitely like to meet up again... for some fun!”
“Awesome!  Where and when?”  I asked.
“I’ve always wanted to have some fun in a movie theatre.  You up for it?”
“Hell Yeah!”

The next day, I called her to make plans to meet up again... this time for some fun.  We decided to see the oldest movie at the quietest theatre.  This way, there would be fewer people in the theatre.  We met up at 8:00pm and went into the theatre.  We chose to sit in a secluded area in the back.  She was wearing a loose fitting, knee length dress.  It was apparent she wasn’t a bra.  I was curious if she was wearing panties!

“How have you never been able to find a guy to do this with?”  I asked.
“I’m not sure!  My boyfriends have all ‘said’ they would do it, but never go through with it.  Promise you won’t back out?”
“I’m here for fun with you... and I’ve seen this movie before.  You have my undivided attention!”

We talked until the lights dimmed and the movie began.  About 25 minutes into the movie, Jessica lifted the armrest separating us and cuddled close to me.  She also started rubbing the inside of my right thigh.  As if the anticipation wasn’t enough to get any man hard, feeling her rub my thigh was making me super hard!  She unzipped my jeans and stuck her hand in.  She found my cock and whispered,

“Wow!  I didn’t expect such a big cock!  I hope it all fits in my little mouth!”

I just smiled and winked at her.  She had a firm grasp on my cock as she tried to give me a handjob.  After a few minutes into the handjob, she slid off the seat and onto her knees between my legs.  She pull my cock out and began sucking my huge head!  She sucked like a pro!  The sensation was amazing!

I looked down at her and our eyes met.  She deepthroated my cock in one fluid motion and held it there for 10 or 20 seconds.  She started bobbing her head on my cock, keeping a tight seal on it.  My old fuck buddy was good, but Jessica was a master!  She pulled off my hard cock and let the cold air touch it.

She mouthed, “Are you close?”
I responded with “Getting there!”

She returned to my cock with a fury, intent on making me cum hard!  I wasn’t going to last long.  We kept our eyes locked the whole time.  About a couple minutes later, I mouthed “I’m gonna cum!”  She gave my cock a couple more bobs and deepthroated my  cock again!  That made me cum hard!  She kept a tight seal on my cock, sucking every last drop of my cum!  She put my cock back in my pants, zipped up my jeans and returned to her seat.

“I love your cock!  It’s the biggest one I’ve ever had!”  She said.
“Thanks!  You sure know how to inflate a man’s ego.”  I responded.

Took me a few minutes to recover.  I slowly slid her dress up.  She noticed and spread her legs a little bit.  I rubbed her thigh slowly until I reach her thong covered pussy.  I found her clit and started rubbing it.  She was moaning softly.  Her thong was so wet!  I figured it was time to return to the favor.  I got down between her legs.  With her help, I pulled her thong off.  I was staring at a beautiful sight!

I dove in!  She pussy was sweet!  I pushed my tongue into her pussy as far as I could.  I alternated between licking her pussy, sticking my tongue in, sucking her clit and swirling my tongue around it.  She was going crazy!  She held my head to her pussy.  I could tell she was close.  I reached up and twisted her nipples.  That set her off!  She was moaning loudly.  I got up and kissed her hard to muffle her moaning.

“Do you have any condoms here?”  She asked.
“Shit! I forgot them at home!”
“OK.  Let’s get out of here!”

We decided to head to her place.   She was masturbating the whole way!  I was having trouble keeping my eyes on the road.  We weren’t at her place more than 30 seconds when she pulled me towards her bedroom.  She removed her dress.  I took that as my queue and got naked too.  She was already on the bed, fingering herself.

“I finally get to see the monster!  Now get over here and fuck me!”
“Yes ma’am!”
“Condoms are in the drawer”

I grabbed a condom and put it on.  I moved between her legs and kissed her.  As I was kissing her, I positioned my cock at her very wet entrance and slowly entered her.  As my entire cock disappeared in her, I hit her cervix.  I slowly pulled out and pushed back in!  Jessica had a big smile on her face.

“I love your pussy around my cock!  It’s so tight!”
“My pussy has never been stretched this much!

We continued fucking in missionary.  Jessica was moaning loudly.  I pulled out completely and stayed that way for a minute or two.  Jessica tried to wrap her legs around me to pull me back in, but I prevented it.  She gave me a puppy dog face.

“If you want my cock, beg for it!”
“PLEASE DAN!  I NEED YOUR COCK!  Please put it back in!”
“OK, but I want to fuck you doggy style now!”
“OOOOO!  My favorite!”

Jessica got on her hands and knees and begged once again for my cock.  I grabbed her hips and slammed in.  I continued the rhythm and Jessica pushed back to match it.  Her pussy was getting wetter with every stroke!  I looked down at her puckered asshole.  It looked so inviting!  I started to push my thumb into it, when Jessica said,

“Don’t!  I’ve never had anything in my ass.”

I pulled my thumb out and continued fucking her.  I was getting tired, so I told her I wanted to fuck cowgirl now.  I lay down on my back and she climbed on top of me.  I lined up my cock with her pussy and she dropped down on it.  She was going crazy fucking me!  I could feel her clit rubbing against my cock!  Jessica was breathing hard.  A moment later, her pussy starting contracting as she yelled,

“I’m cumming!”

Once her orgasm died down, she rolled off.  We cuddled and kissed for a little bit.  I still had not cum.  I took of the condom.

“You didn’t cum yet, did you?”  Jessica asked.
“No, I haven’t yet”
“How can I help with that?”
“I fulfilled your fantasy.  I was kind of hoping we could fulfill one of mine.”
“Seems fair.  What’s your fantasy?”
“I’ve always wanted to cum in a woman’s ass”
“Um.  I said that I’ve never done anal before.”
“Would you be willing to try?  I’ll stop if it hurts too much.”

She agreed to give it a shot.  She got back into doggy position.  I stuck my fingers into her still wet pussy and used her cum to lubricate her asshole.  As I was lubbing up her asshole, I pushed my bare cock into her pussy.

“Are you ready?”  I asked.
“I think so.”

I pulled my well lubricated cock out of her pussy and slowly started pushing into her asshole a little bit at a time.  After every little push, I stopped go let her adjust to my monster cock.   I finally got my entire cock in her ass.  It was an even better feeling than her pussy!

“How does it feel?”  I asked.
“It hurts, but it’s a good pain.”  She responded.
“Let me know when I should continue.”
“Keep going.”

I pulled out until just my large head was in then pushed back in.  The sensation was incredible!  I was fucking her with long strokes.  She was starting to enjoy it, as she was moaning again.  I pushed in, stopped there and reached under her to finger her clit a little.  I felt her hand touch mine.  She took over fingering herself.  I went back to fuck her ass.  I sped up my ass fucking.  My balls were slapping her pussy with every stroke.  She was breathing heavily again, which was a sign that she was close to an orgasm.   As I pushed back in, she came and her ass tightened up!  I couldn’t pull out.

“OH MY GOD!!!  OH MY GOD!!!” She yelled!

After what seemed like an eternity stuck in her ass, she finally released my cock a little bit and I went back to fucking her ass until I came in it!  I pulled out and we both fell onto our sides.  She turned to face me and kiss me hard.  I pulled her tight.  We just lay there silent for a few minutes, when she said,

“Wow!  That was amazing!  I’ve cum so hard!”
“I’m glad you enjoyed it.  I did too!”
“If I knew it would feel so good, I would have tried it a long time ago!”
“I’m glad you trusted me enough to try it”
“Do you want to spend the night?”
“Absolutely!  Besides, it’s not like I live far away!”

Summer With The Rebeccas

ddn2003 on Sex Stories

I was living in Toronto, Canada.  At the time, I was 30 years old, six feet tall and 240 pounds.  I had accrued eight extra weeks of vacation days at work and was told to use it all by the end of the 2008.  I decided to take the summer off from my job and visit the Rebeccas in Dallas, Texas.

I met both Rebeccas online.  As it turns out, they were best friends since kindergarten.  They were both 24 years old.  Over the last two years, the three of us had become close friends.  We spoke on the phone often, about everything from our lives, triumphs, problems and frustrations – including sex.  They had been buggi

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ng me to visit for some time now.

I got off the plane, got my baggage and headed to the exit gate.  While I had sent them pictures of me, they never sent pictures, so I was looking around almost blindly.  All of a sudden, I heard two very excited voices calling my name!  I walked over and said “You must be the my Rebeccas”.

The one on the left said “Of course we are, silly!”

The Rebecca on the right said “Let’s get outta here and start the best summer of your life!”

The whole limo ride to the hotel, I was thinking “Thank you God!”  They were stunning!  Rebecca C was about 5’6”, maybe 120 pounds, large B cup breasts, beautiful long blond hair and blue eyes.  Rebecca P was about the same height, about 140 pounds, C or D cup breasts, shoulder length brown hair and brown eyes.

Rebecca C was telling me that they got a suite in the hotel, so they didn’t have to travel back to Richardson (northeast of Dallas) every night.  We headed up to the suite.  It was huge!  It was more like a 3 bedroom condo, than a hotel suite!  Once again I was thanking God!  This time because I wasn’t paying for the suite.  Rebecca C was a successful local clothing designer and Rebecca P was a teacher at a prestigious private school.  I was told that I’m not paying for anything this summer.

“Ok, Dan.  Now that you’re finally here, what would you like to do first?” asked Rebecca P.

“It’s dinner time in Toronto.  Perhaps, we could go to dinner.”

“Sounds like a plan.  Did you bring a suit?” replied Rebecca P.

“I did.  Why?”

“Because we’re taking you to a nice restaurant, silly!  Go get dressed!” said Rebecca C.

With that, the Rebeccas headed to their respective rooms to get changed.  About 20 minutes later, I thought I died and gone to heaven.  Rebecca C was wearing a tight and very short blue dress with spaghetti straps.  Rebecca P was wearing a slightly longer and looser black dress with a V-shaped neckline.  It really showed off her amazing cleavage!

“I’m going to be the envy of every man there!” I said.

“Why is that?” asked Rebecca C.  As if she didn’t know.

“I’m going to walk in with a drop dead gorgeous lady on each arm!”

“Oh you charmer!” said Rebecca P.

“You clean up pretty well yourself, Dan!” said Rebecca C.

We headed downstairs.  The limo was waiting for us.  The restaurant seated us in a secluded booth.  It was a Dan sandwich!  A beautiful woman on either side of me!  Dinner was out of this world!  Wine, food, dessert and 2 hands rubbing my thighs!  We paid the bill and headed back to the hotel.

In the limo, the Rebeccas took it to the next level.  They started making out with each other!  It was a sight to see!  I came back to earth and realized that our driver was watching everything. I closed the divider, apologizing to him.  Rebecca C broke her kiss to say thank you.  She then got on her knees and stuck her head under the other’s dress.  I wasn’t able to see what was happening down there, but Rebecca P was moaning louder and louder towards an orgasm.

“Keep going Bec!  I’m soooooo... AHHHHH!!!”

Becca (P) was laying there smiling.  Bec (C) pulled her head out.  Her face was covered in cum.  She got back on the seat, grabbed a handful of my cock and kissed me.  Becca sure tasted sweet!  We got back to the hotel and quickly headed up to the suite.

“Wow!  That was...”  I tried to say.

“That was nothing compared to what we’ve wanted to do to you!”  Interrupted Bec.

“Go to your room.  We’ll be there shortly.”  Added Becca.

I headed to my room and quickly undressed down to my boxer-briefs.  About ten minutes later, the Rebeccas entered my room.  My mouth fell open!  The two of them struck a pose before passionately kissing each other.

Becca looked at me and said “I take it you like what you see?”

She was standing there see-through red teddy and stockings.  I could only nod my head up and down.

“Becca, I think that means yes!”

Bec was wearing the skimpiest black lace bra and thong.  At this point, I’m pretty sure I was drooling.  They both climbed on the bed, Becca on my left and Bec on my right.  They leaned over me and made out again.  Bec broke the kiss, looked at me and then my cock.

“Judging by the tent in his draws, I think Dan is feeling left out”

“Sorry Dan.  We’re all yours.  What would you like us to do first?”  asked Becca.

“Um... How about the two of you undress each other?”

With that said, they began to seductively undress each other.  They then turned to me and began yanking at my underwear.  My cock is only about six inches long, but it’s pretty thick.

“Ok Dan.  We’re all naked.  Now what?”  Asked Bec.

Looking at Bec, I replied “You did an awesome job of making Becca cum in the limo, but you and I haven’t cum yet.”

Bec got on top of me in a 69 and started sucking my cock.  Becca and I took her queue.  I began to eat Bec out, while Becca joined Bec in sucking my cock and playing with my balls.  What a feeling it was to have two mouths and four hands touch me down there all at the same time.  I was getting close and apparently so was Bec, as she was focusing on her own pleasure.  It wasn’t long before Bec came hard and squirted all over my face.  As unexpected as that was, it set off my orgasm into Becca’s mouth.  The two of them shared a passionate kiss above my cock.

“Bec, you never told me you were a squirter!” said Becca.

“That was the first time in a long time that I have squirted.  Sorry Dan.”

“Sorry for what?!  That was awesome!  It’s always been a fantasy of mine!”  I said.

“Well then... Your welcome!”

“Ladies, if you’ll excuse me, I think I’m going to rinse off my face.  Don’t do anything without me!”

A couple minutes later, I returned to find them in a 69.  Becca was on top.  I had a perfect view of Becca’s fine ass and pussy!  I walked over to them and made eye contact with Bec.  She grabbed my cock and lined it up with Becca pussy.  I grabbed her hips and slowly pushed in.

“Oh!  Mmmmm!”  Moaned Becca.

I started fucking Becca faster.  Bec started fingering Becca’s ass.  We were going at for about ten minutes.  Becca’s pussy was almost form-fitting around my cock.

“Becca keep working my clit!  I’m so close to cumming!”

I chimed in “Me too Becca!  Your pussy is amazing!”

“Dan, cum in my ass!”

Bec pulled her fingers out of Becca’s ass and I pulled out of her pussy.  I pushed in until my cock head was almost in and pulled out.  I repeated the process again and was pushing in again when Becca said “Stop teasing me and fuck my ass!” as she slammed back against my cock.  I was now all the way in her ass.

“How badly do you want me to cum in your ass?  Maybe I’ll keep my cum for Bec!”  I said.

I got my answer my answer when she started working her ass muscles and tightened her grip on my cock.

“Ok, Ok!”  I said.

Just as I started fucking Becca’s ass, Bec came hard.

“Thanks Becca!  That was amazing!”  With that said, Bec went back to eating Becca’s pussy.

“Keep going you two!  I’m close!” Becca said, just moments before she came.

She stiffened up, which set me off.  Spurt and spurt of my cum went deep into Becca’s ass.

“So Dan, don’t ya wish you had visited long ago?”  Asked Bec.

“Hell yeah! But we ain’t done yet!  I haven’t fucked you yet!”  I replied.

“We have lots of time this summer for that!  I’ll be right back.”  Becca said.

I got under the covers with Bec.  A few minutes later, Becca joined us under the covers.  We all fell asleep together.

I awoke the next morning alone in bed.  I walked into the bathroom to pee and heard some noises coming from my shower.  I looked over and saw the two of them making out in the shower.

“You couldn’t wait for me?!”

“No, we figured you were tired.”  Becca replied.

“Any room in there for me?”

“Plenty, but we’re just about done in here.”  Bec answered.

“Are you ready for round two?”  Becca asked.

“Hell Yeah!”

I watched the two of them dry each other off.  Bec and I started making out on the bed, while Becca disappeared.  Bec was on top of me.  She lined up my cock with her pussy and sank down.

“Mmmmmmm!  Becca was right your cock feels amazing!”

We started fucking.  Hard to imagine a better feeling than Becca’s pussy or ass, but I had found it!  We had a good rhythm going when Becca finally returned.  She was wearing a strap-on dildo.

“Hey Bec!  How about Dan and I fulfill a fantasy of yours?”  She asked while walking up to the bed.

“Which one?”

“The one where Dan and I fuck your pussy and ass at the same time.”  Becca replied.

“You had to ask?”

Bec and I stopped fucking for a moment.  Becca grabbed the rubber cock and guided it into Bec’s ass.

“Oh my God!  This feels awesome!  Both of you start fucking me NOW!”

We did as we were told.  We quickly developed a steady rhythm.  Bec was in ecstasy.  I found it hard to believe, but this was the first time Bec had tried double penetration.  I was kind of honored to be part of her first time.

“I’m cumming!”  Bec tried to say.  It sounded more like “I’m cu....”

“I’m close!  Where do you want my cum?”  I asked.

“She’s on the pill.  You can cum in her pussy!”  Becca responded.

“Bec?”

She managed to shake her head yes.  I let my cum squirt all over the inside of her pussy.  Becca pulled out of her ass and Bec rolled off my cock.  Becca took off the dildo and went to work on Bec’s cum filled pussy.

“My cock could use a cleaning too Becca!”

“Don’t worry Dan.”  Becca replied.

Bec came again.  She was exhausted.  Becca turned to me and began cleaning my cock.

“Sorry Becca, I don’t think I’ll be able to cum again.”

“That’s ok.  You and Bec rest up.  I have some school work that needs to get done.  I’m going to go get dressed and head into the school.  I’ll meet you later for dinner.”

Bec and I fell asleep spooning.  My cock nestled between her ass cheeks.

It was an awesome summer!  The Rebeccas took me to see all the sights of the city and of course, I got to see more of their kinky side!  As Bec had her work and Becca had summer classes to teach, I got to spend some time with them individually.

By the end of the summer, Bec and I had fallen in love.  I requested a transfer to Texas so we could continue our relationship.  It’s been eight months and Bec and I are still dating.  Becca has since met a guy of her own.  We make quite the foursome!  ;)