Being a freshman in college is difficult I know because I was there once. Now I am a senior and I have learned the ropes and school is no problem. I have learned how to handle most situations. My experiences have come in handy with my new roommate, Holly. I am kind of her big sister and I am able to help her with almost every problem. How to study; how to go to class with a bad hangover; and which frat parties to stay away from.

Last night she came to me with this unique situation. You see her and her boyfriend, Bob have been having problems. Problems of a sexual nature. I being the big sister decided to help her in this situation. You see although Holly was sexually experienced and no longer a virgin she was having problems with full penetration. She thought she was wet enough but it was still painful when Bob would enter her.


I told Holly that sometimes the problem is in her head and she needs to think about her relationship. Other times it could be physical. I told her I could help with the physical part but as far as her emotional feelings, that was something she had to work out with Bob. Holly understood but was confused on how I could help her with the physical part. I reached under the bed and pulled out a strap on dildo. Holly's mouth dropped open as I showed her my favorite toy.


"What are you going to do with that?" she asked. "I am going to open you up a little so things will be easier for Bob." I told her. She examined the dildo and told me Bob was not that big. So I guess if she could take the entire dildo she should have no problems taking Bob.


We proceeded to undress and I started my examination of Holly's troubled spot. Spreading her pussy I could tell lubrication was not the issue. She was wet, very wet. I had no problems inserting a finger into her and then two and then three. As I slid my fingers in and out Holly reached down and rubbed her clit. I was amazed as I slide my fingers in and out and watched as she came in just two minutes.


Well now that she was ready I thought it was time for some fucking. Holly helped me strap on the ten inch dildo and positioned herself on the edge of the bed. I slid the head of the dildo passed her pussy lips and started to enter her very wet pussy. I watched as Holly bit her lip as I pressed further. I was going slowly until Holly let out a scream in pain.


I pulled out so Holly could relax and I then tried again. Going slower this time I got about four inches in before Holly told me to stop. Again I used my experience and suggest we should try a different position. Turning Holly on all fours I tried a rear entry approach. I climbed up on the bed behind her and slowly slid the plastic cock into her.


I started with a couple of short strokes keeping my hand on the shaft of the dildo so no more then four inches entered her. I kept my hand in place as I picked up the pace. In and out harder and harder but only four inches at a time. When she got used to the fucking I pulled my hand away to go deeper. As she screamed out I kept on fucking her.


I must have slammed about six inches into her before she finally collapsed in pain.


Well we were making progress. She had gone from four inches to six inches I thought it was time for another position change. I lay down and had her straddle me. This way she could be in control.


She positioned herself on top of the dildo and started slowly fuck the cock. Again just short quick strokes and she got used to her pussy being stretched. Up and down she bounced as she took more and more of the dildo. I watched as it went deeper and deeper. Holly then turn around so was facing away. I could watch as she fucked herself. Her pain turned to pleasure as she opened herself up.


"Look at me" she screamed. "I am fucking. I am taking the whole dam thing." Holly continued her assault on the plastic cock. Bouncing up and down harder and harder, deeper and deeper with every stroke. I was just watching as she fucked herself.


The next day Holly told me that Bob gave her a good fucking and it was all because I had opened her up. Being the big sister is going to be fun for me.