The Holiday... [Part Three]

It was the day after our little accident when Mark came inside me. The following night we didnt have sex, instead just having a snuggle up in bed. During the following day we managed to contain our sexual feelings towards each other. I knew we both probably wanted to but secretly I was planning on asking Mark something and I wanted to make sure he was really wanting sex before springing it on him. The day itself was pretty dull, spending the time at the pool, sunbathing and having a laugh. My plan would kick into life at night.

It was about 6pm, I had just came out of the shower and Mark went in after me. As Mark was in the shower I got ready to go out. I put on my sexiest underwear set that I had. A nice black lacey set. On top of that I put on my sexy black dress that barely covered my bum and gave me a half decent cleavage. I knew this would be the dress to make Mark do whatever I wanted and I hoped that it would do just that, especially with what I was planning on springing on him later tonight after our meal.

After our meal at night we went down to the beach which wasnt a wise move wearing heels although after I took them off I was fine. We sat on a sun lounger on the beach watching the sun setting and thats when I decided to ask him. I explained to Mark that Ive loved doing different things with him and that I had experienced alot while seeing him however pointed out there was one thing I had wanted to do... anal sex. I saw Marks face and he looked a little put off. I kept on going telling him that I had experimented on my own but would love to even try it with Mark as I trusted him. Mark then eventually spoke up and claimed he had done it before and the previous partner had found it sore and painful so he didnt want to do it incase he hurt me. After a bit of back and forth discussion I eventually won Mark over to at least attempt it. Excited by the development we both went abck to the apartment. On the way he mentioned lube however I had secretly brought some knowing I was going to ask him. It was then he must have realised this had been pre-planned.

We got back to the apartment and I took out the lube from my suitcase. Mark just smiled as he locked up the door and we made our way through to the bedroom. Mark put his arms around my waist and we kissed, his hands running over my bum and eventually his fingers started probing under my dress. His hands then ran up my back as he reached for the zip and unzipped te back of my dress. Still kissing he pulled the straps down and my dress fell away from my body revealing my sexy underwear. I then took off his shirt and unbuttoned his trousers so that we were both standing in our underwear. Slowly we moved onto teh bed, still kissing until I unclipped my bra and took it off, throwing it on the floor. Mark then began to kiss my breasts, sucking gently on each nipple as he moved over them. He moved down my body until he rolled off my pants.

Mark wasted no time in plunging his head into my pussy, licking away and sucking. He was really good at this, he knew exactly how to get me going. One of the many things I loved about him. Soon he stood up and removed his boxer shorts and I shimmyed over and grabbed his cock and put it straight into my mouth. I sucked away at his cock, going pretty deep at times. I kept up this for a good 4-5 minutes before Mark asked if I was sure I wanted to do this. Of course i said yes as it had always been something I had wanted to experience. I wasnt really sure what I was to do however Mark got me into the doggy position and he spread my cheeks apart. He said it looked really tight however before I could reply Mark began to lick around it. I had never experienced it, it was a strange sensation but I loved it nonetheless.

After putting his tongue into my ass a few times, another strange sensation, Mark took the lube and put some on his finger. I felt him rubbing his finger against my asshole before he pushed it in. It wasnt that bad, he was able to start fingering fairly hard and I fine with it. Eventually Mark increased it to two fingers and I was still okay with it, it did feel a little more painful when he fingered but the pleasure outweighed the pain. Mark then squirted some lube around my asshole, it was a little cold which was a bit of a shock but I didnt mind. He rubbed it around the hole and once he had his condom on, put a little extra on the condom. We were now ready for the main event.

Before he pushed it into me he told me to relax and explained what I should do and to tell him if its too painful. I knew all this already having researched it all but I let him go through it all again. I felt his cock running between my cheeks with each push he was pushing a little harder against me. I was beginning to wonder if he was ever going to penetrate however before I could mention anything I felt a sharp shock to my system as the head pushed into my tight ass. Mark pushed in very slowly. I wont lie, there was some pain but it was nothing I couldnt handle. It wasnt too painful that I had to stop and if this was as worse as it gets, I could easily do this all the time.

After he penetrated my ass with his hard cock, he allowed a few moments for my ass to get used to his cock being inside of me before he began to pull out and push back in slowly. He kept asking if I was okay with it and I kept telling him that if I dont say stop, then im fine. After a few minutes of slow thrusts he began to pick up the pace a little. As he began to go a little harder and faster i reached down to start playing with my pussy as he fucked my ass. After another few minutes we were going th same pace and hardness as regular sex and I was still loving it. It was a totally different experience to regular sex for me but I was still loving every single thrust.

Mark pulled out and moved me onto my back. He didnt waste too much time and pushed back into my ass, it was much easier than before and my ass put up much less resistance to him. I played with my pussy as he grinded away at my ass. At this point I was having wave after wave of sexual pleasure, possibly due to my playing but probably down to a mixture of both. It wasnt long before I heard Mark let out his groan and I could feel his cock throb inside my ass. I knew he had cum as he slowly pulled out my ass. All i could say was wow. I loved the anal sex and I cant believe I hadnt done it before now. Mark took off the condom and I went through to the bathroom to clean up a little.

In the bathroom I had a sneaky look at my asshole, spreading my cheeks to see that my ass did looked "used". I could easily slide fingers into it with not much resistance but I wasnt worried, I knew things returned to normal soon. After cleaning up I went back through to Mark and lay beside him in the bed. We spoke a little about the sex and I assured him I loved every moment. Mark then revealed that he loved it aswell saying my ass was really tight and he was surprised he lasted as long as he did. He said he would do it again sometime although did reveal that he would rather have regular sex to anal. I didnt mind really... I just loved sex. We spent some more time talking before getting some clothes on to sit in the balcony however I had now experienced all the sexual things I wanted to. Anything new from now is a bonus. My ass was still felt a little strange but I didnt care. Anal sex rocks.

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Note: Part three so soon after the last part ;) Had some time to kill so thought id write it up. Dont know if there will be two or three remaining parts to this, there are some things I could skip. Ill decide later though. Enjoy the story everyone and rate and leave comments please :)
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Posted by StephyX
4 years ago    Views: 691
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4 years ago
Great success of a well-planned seduction by young horny Stephanie!
Such a tasty story! ;-)P
4 years ago
out of this world love reading everything you put on here
4 years ago
My stories with other people will be coming, im following a timeline but I plan on skipping a year or two so that im not repeating the same things.

Thanks so far to everyone who has commented :)
alibalibabe
retired
4 years ago
Stephy this is excellent! How about some of your adventures with other people?
4 years ago
stephy i want to hear all of the sweet naughty little details you are so good at this lil'darlin