A Night Of Firsts


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 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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.

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    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.