Hotel Bliss Guest Blog

Never Have Sex With Your Fiance’s Sister - Part I

  I didn’t plan for anything crazy to happen when I invited my best friend, Wendy, over to the apartment I shared with my boyfriend’s sister. We both had the day off and just planned to watch movies and hang out. A couple of hours into our fun, Holly (my roomate) showed up with a man about our age whom I hadn’t met - not unusual behavior for Holly; we always joked about who was going to be the next Flavor of the Week.

  His name was Tom. He was tall, thin, lanky with glasses, and had a nice smile. He wasn’t my type physically, but he seemed like a pleasant man and so we all chatted for a while and just generally hung out.

  As young people do, we soon got restless and decided to go out. I thought, why not take lunch to my boyfriend at work? So we all piled in my car and headed out. The two in the back were getting cozy, and my best friend made a statement. You know the kind that hides a bit of truth behind a short laugh?

 ”You guys are starting to make me jealous!” she said.

 To our surreal surprise, Holly reached her hand up front to touch Wendy’s breast.

 ”Here,” she flirted, “You don’t have to be jealous.”

 The still sex-shy girl inside of me made my eyes widen, as the vixen in my chest caused a giggle to come from a sly smile.

 ”What about me?!”

 Suddenly I had four hands upon me as I gripped the steering wheel, trying to keep steady on the road. I loved the feeling…it all seemed so taboo! One of my breasts was being fondled by… I didn’t even know who, while another hand was creeping up my inner thigh. I’d always thought girls were beautiful and wondered if I might like to be intimate with one…though my very christian childhood prohibited it and until just recently, I’d always pushed away the idea as something wrong. Now here I was with two girls all over me as they kissed each other, and a man whose last name I didn’t even know was watching from the backseat!

 ‘You’re driving to your boyfriend’s work,’ a tiny voice in the back of my mind kept telling me, ‘You’re driving to your boyfriend’s work.‘ Somehow it got pushed aside by the curiosity that was still pounding in my chest.

  Oh how I should have listened.

  We reached our destination and pulled ourselves together to walk inside without looking suspicious. As wrong as it was - and it truly was - it somehow made everything that much more tantalizing. We all sat down with my sweet and adoring boyfriend and eyes darted across the table as I flirted with my best friend and looked at his sister in amazement; SHE’D TOUCHED ME! So wrong. So exciting!

  I remember seeing Tom there as…not an enticement for sex, but soley because he made it even more off limits. I’d never had sex with another person in the world other than my boyfriend, much less a threesome…but a FOURSOME!? How many times in your life do you get the chance to do that sober and so casually as was presented to us that day?

  A half hour later we left the establishment and I threw the keys at Holly, “My turn in the back!”

 I pulled Wendy in behind me as I crawled in, forcing the man to the front. Ha! Now the fun was going to begin…Holly adjusted the rearview mirror so she could watch us as we played with each other. Our hands began exploring beneath the shirts that covered our sensitive round busts and we kissed that sweet kiss that only women can have between their soft lips.

 ”Okay I’m getting lonely up here, that’s no fair!” We smiled and leaned up front to include the driver in our fun.

  By the time we finally got home, we were all so worked up that we raced inside and into my bedroom, where we found a queen sized bed waiting for us.  I stood there a bit shyly - not sure what to do, but anxious to do something. Wendy soothed my anxiety when she pulled me into the bed and climbed on top of me, fondling and giggling with me over the sheer odd fun we were having. Tom laid down next to me with Holly and we played as seperate couples in the dark. I felt shy and scared and like I was doing something wrong, but wanted to experience it so badly that I closed my eyes and tried to push all thoughts out of my mind. Wendy reached over and felt the two beside us, and the moaning began.

  Holly very much enjoyed a woman’s touch while Tom was slipped inside her. I reached out and slid my hand across her stomach and up to her chest, barely seeing her mouth open and eyes closed in the dark. She rolled off of Tom and I saw a nine inch penis hard and ready to go. He sat up and took Wendy under him. I kissed her as he inserted himself into her soft genitalia. He worked her long and hard until she finally shouted out as she orgasmed. I took a breath then, partly for realizing I’d just helped a girl come, and partly because I knew it’d to be my turn next.

  I was scared shitless.

   I felt Holly pulling me closer to her and positioning me right under Tom. The girls were touching me and kissing me and that helped me relax again, but before I knew it there was a male member inside of me, hitting me rough and going in as deep as it could. I didn’t like it one bit.

   ‘I thought that giant dicks were supposed to make a girl feel GOOD?’

  It was terribly uncomfortable and even hurt; he was jabbing me, as if he were a boy poking a frog with a stick! I felt as though I could feel him bruising my stomach - despite 21 years of having that thing attached to his torso, he still had no idea how to use it! My boyfriend was such a great lover, it never occured to me that anyone could be so utterly terrible at something so standard an activity.

  My boyfriend.

  From that moment I lay there, waiting. Simply waiting.

  When will this be over? Oh god this is so annoying. I just know I’ll pay for this later…

  Finally he got off me and switched to one of the other gal’s, and I decided to take a break and watch. They seemed to be having a good time…well, let them. When we were finished, we flirted and acted silly, playing around and making jokes. Then, Tom made mention of his camera.

  WARNING: Never…EVER…under ANY circumstances allow ANYONE that you don’t completely and FULLY trust to take pictures of you while in an incriminating state. i.e. Naked with your boyfriend’s sister and some strange guy while you wrap your legs around your best friend.

To Be Continued……

Be on the lookout for Part II, when an engagement, lies, karma and a two-tongued devil take over the real life characters of Never Have Sex With Your Fiance’s Sister