August

As stated in my previous fantasy, Why Don’t We Help Each Other Out, my older sister, Dee, and I had a very special moment in June.  During the following weeks, Dee showed no interest in repeating what had happened in June.  I was taken aback by her behavior, but I wasn’t going to make an issue out of it.

Let me remind you of Dee.  She was a college student at home for summer break.  Dee is 5’ 6” and weighs about 125 pounds.  She has a full head of beautiful, black hair that is shoulder length and a little curly.  She is very fit.  Her ass is stunning, and her 34B breasts scream “suck me”.  Her pussy mound is just as thick and black as her head and as soft as silk. 

As I normally did each workday, I took my shower mid-morning.  I wrapped the towel around my waist, combed my hair, and head to my bedroom.  As I walked to my bedroom, I looked in and saw Dee was laying on her twin bed.  She had on a camisole top with matching shorts.  Her head was turned away from the door.  Her arms and hands were under her stimulating her pussy.

I stood there enjoying what was happening in front of me.  I quietly stepped up to the edge of the bed.  With my right hand, I slowly started to caress her ass, and, with my left hand, I massaged her neck and back.  “Remove my shorts and panties,” Dee instructed.  I removed them as requested.   I then continued to caress her ass.  Eventually, Dee started to raise her ass a little as I caressed it.  I took this as an indication she wanted me to stimulate her pussy.  I turned my hand and slid it down her ass until I was able to touch her pussy and tease her clit.  We continued this petting and teasing for quite some time.

Eventually, Dee turned her head to the left and looked up at me with a beautiful smile.  “I really want you to make love to me, but we can’t!  I really want to know what it feels like to be fucked.  I want to feel a cock in me!  I know you’ve done this with girlfriends, but I never have, and I really want to experience it!”

“Well, I don’t think I should be the one that does that for you.  I mean, you don’t want to risk getting pregnant by me, do you?”

“No, I don’t want to risk that, but I just want to feel the pleasure of being fucked,” Dee said.

After a few minutes of kissing and caressing, I looked at her and smiled. She really wanted more but within limits and I am not good with limits.

“Dee, do you trust me?” I asked.

Dee cocked her head slightly and said, “I’m laying here naked with you, and you asked me if I trust you?  Of course, I trust you!  Why?”

“Well, why don’t you roll over and relax?  I’ll see if I can help you,” I stated.

As Dee rolled over on her stomach, I got up and got some lubricate from her dresser.  I poured a small portion on her ass with specific attention to her crack.  With that done, I climbed back on the bed and straddled her ass.  I slowly started rubbing my cock up and down her ass.  I kept rubbing her ass lower and lower.  “Dee, pull your knees up under you and raise your ass up a little,” I requested.  Dee complied and got into a modified doggy-style position.  With her ass up, I stroked my cock from the top of her crack to the folds of her pussy.  Dee was thoroughly lubed and turned on.  My cock was covered with lubricant as well.  As I stroked her, I paused with the head of my cock on her ass button. 

“Okay, here is what we’re going to try.  Push back into me at your own pace and try to relax!”

Dee pushed back, and the head of my cock slowly slide into her ass.  “How does that feel?” I asked. 

“It’s okay.  It’s a little uncomfortable but it doesn’t hurt,” Dee stated. 

“Well, you take your time.  Slowly push back and try to rock on my cock.  Do it at your own pace and comfort.”

“Okay, I can do that but if it hurts too much I’m going to stop.”

“That’s fine.  I don’t want to hurt you.  I just want you to experience the feeling of a cock in you.  It might help if you pleased yourself while you did it.”

Dee slowly began to rock back and forth while stimulating her clit.  As she did this, I kept putting a few drops of lubricant on her ass and the top of my cock.  After about two minutes, Dee paused and asked, “How much of your cock is in me?”

I looked down and smiled, “It’s all the way in.”

Dee began to pick up the pace with me staying as stationary as possible.  She paused and said, “I want you to do the work.  Go slow but fuck me!” 

“Your wish is my command!”

I held Dee by the outside of her hips and began to fuck her tight ass.  With Dee’s encouragement, I increased the pace.  She was playing with her clit and announced she was close to having an orgasm.  I was at the same point.  My balls were about to explode.  I stopped and said, “Dee, roll over on your back.  I want to see your face when you cum.”  I eased back to allow her to roll over on her back.  With her in the receptive position, I climbed between her legs and had her bend her knees and pull them towards her breast.  I positioned my cock on her tight little asshole and gently slide it into her.  The tightness was amazing!

Dee started pleasing herself while I fucked her ass.  Within a minute or so, Dee stated she was going to cum, and I’d better hurry up or be left behind.  I picked up the pace.  Dee let out a very loud moan and started climaxing.  At the look on her face and her moaning, I thrust into her ass and exploded.   After I unloaded about four streams in her ass, I stopped and looked down at her face.  The sight was unbelievable.  Dee was smiling with her body occasionally shuddering.

I bent down and kissed her.  Dee threw her arms around my neck and stated, “That was amazing!  I’ve never had such a strong orgasm!  Is the orgasm as intense when I have a cock in my pussy?  I can’t imagine it being more intense!”

“Trust me, if the guy knows what’s he doing the answer is yes!  There are places within your pussy that a cock can really stimulate,” I stated.

Dee returned to college the following week and that was that!  That being “unbelievable!"