Obsession of the Mind Ch. 05

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Truth or dare game enables Chris to compare to previous b/fs.
2.8k words
4.22
54.5k
21

Part 5 of the 8 part series

Updated 10/29/2022
Created 02/26/2010
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k4d0h1
k4d0h1
109 Followers

I stripped quickly and jumped in the shower. Using generous amounts of soap I freshened up thoroughly. Rachel was all talk and I was dying to hear more about her past lovers. The liquor was taking full effect as she lost all inhibitions to try and hide any detail from me, her current boyfriend.

I didn't have any boxers with me so I left the bathroom with just a towel. Hoping to skip to my room unnoticed. I quietly opened the door. The TV was still on. It had only been five minutes since I had cum all over myself to the discovery that the guy who followed in after me was well over seven inches long.

I tiptoed behind the couch to get to my room. As I did, I peered over and saw the tan skin of her left knee. I crept closer, more of her flesh came to view. I saw her right foot was propped up on the right arm rest of the dark leather couch. Her left leg was hanging of the front. I glanced at her face and saw that her eyes were shut. Her right hand was resting on her bare stomach and her left arm was at her side. I moved just a bit closer and saw she had removed her shorts and was now wearing bra and panties only. What I saw next was so beautiful and intensely erotic.

I walked around the couch closest to her feet and focused between her legs. The left flap of her extended pussy lips had apparently become stuck to the inner side of her left thigh. As a result her less than modest thong did no justice to hide the fact. Her pussy was literally hanging out of her panties. The dark fold was slightly wrinkled but looked oh so delicious. I noticed the slight bulge her right pussy lip left, still concealed. The sight was overwhelming to say the least.

I adjusted my towel as to allow access of my right hand. After a few minutes of enjoying the spectacle let out a slight moan and began to resituate her body. I jumped back in fear she might open her eyes and see me. After the noise of her skin reluctantly sliding across the leather stopped, I thought it was safe to move closer again. I focused on her face and saw that her eyes were still closed. She was now lying on her left side with her back facing the back of the couch. Both of her legs were brought close to her chest. Her big ass was on full display covered by fabric half an inch thick. That half inch was not near enough to conceal her bulky pussy. It was hardly enough to cover her asshole. There was not a hair in sight. She was completely bare. I assumed she had electrolysis done in the past three years.

I continued to jerk off while admiring her sexy attributes. I figured she was out for the night so I dropped my towel. I got on my knees and crawled along the front of the couch. I stopped. Her feet were close to my face and behind that was bronzed ass being split by the pink thong.

I had always wanted to fuck her ass but dared not bring it up. I recalled the past when she told me she would never allow anyone's dick inside there. I began to feel adventurous and put my left hand on her ass cheek. Big mistake as soon as I did she began to stir. Her eyes opened and slowly focused on me jumping back with no doubt a guilty look on my face.

"What are you doing?" she asked. She began to stretch her legs to sit up.

I frantically grabbed my towel to cover up. "Nothing, I, uhh... I thought I saw a mosquito on you." Nice cover I hoped.

"Why are you naked?" She was still half drunk, but the shock of waking up to me with my hand on her ass likely sharpened her senses.

"I just got out of the shower... and then my towel fell off," I replied.

"Mm-hmm," she uttered. She had to have known foul play was involved. She poured her self another glass, not caring about having any ice. As I was wrapping my towel around me she asked, "a mosquito yeah right. Why is your dick hard?" The expression on her face was one of annoyance and anger.

"It's always hard. I just got out of the shower and was about to put my clothes on."

"Then go put them on." She got up and headed to the bathroom. I quickly made my way to my bedroom and put on some fresh boxers and a white t-shirt. I went back to the living room and sat back on the couch. I heard the toilet flush. She came out grabbed her bottle and glass and started to head for her bedroom.

I had to say something. "Rachel, wait I need to talk to you."

"What do you want? I'm tired and going to bed," she replied with a serious attitude.

"I'm sorry for lying to you," I quickly replied. It at least stopped her in her tracks.

"And?" she asked.

"And I'm sorry for being a pervert," I said.

She smiled. Thank God. "Don't ever lie to me again. This is your only warning."

"I promise, never again," I pleaded. She seemed to be more concerned that I lied than the fact that I was technically molesting her while she slept.

"Good, now what were you doing a minute ago?"

"I was jerking off and I put my hand on your ass, then you woke up," I said.

"That wasn't so hard now was it? And what were you thinking while you were jerking off?" she asked.

"I was... uh... thinking about your ass and uh... fucking it..." I stuttered.

She gave a wicked smile and sat back on the opposite side of the couch downing her drink in the process. "Thinking about fucking my ass? I'm sorry but that is not going to happen. It hurts too much."

Whoa, she just implied she had tried anal. Some lucky bastard got to fuck the most desirable ass on the planet. "You've tried it before?" I asked.

"Hmm... maybe," she smiled. What a sensational tease this beautiful woman was.

"A good hurt?" I asked.

She was acting drunk again. Well not acting. "It can be, but I'm not going to do that with you so get over it."

I couldn't help myself and suggested, "Well at least with me it wouldn't hurt much."

"And why is that?" she laughed.

"Well you know..." I replied.

"No, tell me."

"You know... because my dick is small," I was defeated once again.

"Hmm... That's true. Who knows? Maybe someday,' she said.

"My birthday is next week. Hint, hint," I implied.

"We'll see." She continued to nurse her drink.

"When did you start doing anal? I remember before that you told me you would never do it." I asked.

"I don't know maybe like a year ago," she smiled and asked, "Truth or dare?"

"Serious?" I said, "Okay... umm... truth."

"Chicken," she laughed, "Okay. You really never slept with anybody but me?"

"Easy, yes." I replied. "Truth or dare?"

"Truth."

"Okay. So lets see. If you slept with seven guys after me and one guy before me that would make nine total. So out of those nine how many got to fuck your ass?"

"Umm... one... two... three... four... yeah four," she laughed.

"Four guys but you say you don't like to do it. Yeah right," I laughed.

"Well they liked to do it more than I did," she laughed. "It's not like I did it all the time."

"Okay, fair enough."

"Truth or dare?" she asked.

"Okay, dare."

She smiled and said, "I dare you to... I dare you to not touch your dick the rest of the night."

I showed my contempt but agreed. "Truth or dare?"

"Truth," she laughed.

"Fine... umm... What's the biggest dick you've ever fucked?"

"Pervert! Fine. That would be EJ. His dick was almost too big. Almost," she laughed.

"But how big was it?" I interjected.

"I don't know I don't go around measuring everybody's dick you know."

"Okay, hold on a minute." I ran to my bedroom and grabbed a ruler.

"Oh my God you're such a pervert," she laughed as she saw me carrying the ruler back.

"Shut up," I laughed. I handed her the ruler and said, "now give me a guess."

"God you are so obsessed," she laughed, "okay maybe like to here." She pointed at the nine inch mark.

"Holy shit, that is fucking huge! You can't be serious."

"Wait do you mean who was the longest or thickest?" she said asking innocently. "Because Jason's was definitely the thickest." "How thick was it?" I asked.

She held up her hand and made a semicircle with her thumb and index finger. To my estimation it was similar to that of a coke can. "Like this, I remember I couldn't get my fingers around it."

I would compare the thickness of my penis to that of C battery. There was no comparison. My girlfriend's pussy has had some serious stretching in the past and knowing it was driving me crazy. "Wow, you went from me to him that must have been a serious change," I laughed.

"Yeah it took some getting used to, but after a while it started to feel really good. Like really, Really good," she said.

All this talk made me want to see her pussy again. To see it and imagine it being stretched like that. "Truth or dare?" I asked.

She didn't catch on that it was her turn to ask. "Dare," she smiled.

Perfect. "Okay I dare you to get completely naked."

"Fine, I like being naked anyways." She removed her bra and thong but made no effort to do so teasingly. I wasn't about to complain.

"Truth or dare?" she asked while leaning back and crossing her legs.

"Truth."

"Why do you keep asking about everyone's cock size?" she asked looking directly in the eye.

"Okay... Well I guess it has to do with you having more experience with me. And when you tell me how big they are I guess it helps me understand more what experience you have." I replied ignoring the big point that it was an absolute huge turn on to hear her exploits with huge cocks.

"I see... But what difference does it make that they were bigger than you?" she asked.

"Well, I like hearing about your past and when you told me every last guy you ever slept with was bigger than me it has always stayed in the back of my mind."

"It turns you on to hear about all that stuff?" she asked with an almost loving tone to her voice. As she did so, she lifted her leg up on the couch completely exposing her pussy.

I stared directly at her glorious mound and muttered "Kind of."

"That's okay sweetie, it turns me on to talk about it too. I just never thought you would like hearing about it so much." She said kindly.

"Yeah it's perverted though. I don't know why I think that way," I said sheepishly still fixated on delicious cock hungry cunt.

"It's okay, but think about me. I don't want to tell you everything and sound like a total slut."

I looked up and said, "no, I don't think that way about you at all. I think of you like some kind of sexual Goddess."

She laughed, "Sexual Goddess? Huh?"

"Yeah I do. I would do anything for you. I love you and I love how sexual you are. It's amazing."

"Thanks," she smiled. "Are you hard right now?" she asked.

I had been for the past thirty minutes. I guess the way my boxers were fluffed up she couldn't tell. I pressed the fabric down and let my little erection poke through the fly and said, "yes, extremely."

She stared at it and smiled. "Do you want to touch it?"

"Yeah." I smiled.

"Okay play with it for me." I began to stroke it slowly up and down while staring at her pussy. "What are you thinking about?" she asked.

I replied, "I was just umm... thinking about your pussy."

"What about it?" she asked. Her right knee was raised toward the ceiling while her left leg was propped up horizontal to the couch. Her right foot rested a few inches from her pussy. She began to rock her right leg side to side. Her pussy ever so slightly was moving along with it. Her elongated pussy lips were stuck together as a result of her previously crossed legs.

I didn't immediately answer her but instead continued to gawk between her legs anticipating the moment that her lips would separate. She pulled back her left knee. It was resting below the left arm rest. As she did, her flaps broke free. They were now uneven with her right one slightly raised higher than the other. A dark red slit was now in view.

She lowered her hand to spread her lips open while middle finger disappeared inside her tunnel. As she slowly raised her hand her pussy was much pinker with the light causing her juices to glisten. Her pussy hole was the same diameter as her finger. Which made me wonder why she didn't feel tight around my thicker penis.

Her hand returned and this time she slid her first two fingers inside. When she removed them, her hole appeared wider but returned to its original state within a few seconds.

"Well, what are you thinking about doing to my pussy?" she asked.

Time to score some points. "It looks so tight. I'm amazed at how tight it is after having some of those bigger dicks inside of it." I lied. It appeared a bit loose and that was erotic to me, I just knew she wouldn't think the same.

"You think so?" she asked.

I'm sure she loved to hear about it as it could possibly have been an insecurity for her to think she was loose. "Yeah it felt as tight last week as it did when we first met." Total lie. That tight teenage pussy was not the same.

"That's good to know," she smiled. She was glowing with self approval. "I just wish these weren't so long." She lightly pulled at one of her labia minora.

"Hmm... I think they are sexy. It makes your pussy look very sexual." I explained.

"Yeah only one guy ever said anything bad about them," she said.

"What did he say?" I questioned.

"I don't know, something about how they were bigger than normal," she said.

"That's stupid, all you would have to say is that his dick was bigger than normal. But that doesn't make it a bad thing."

"Yeah I guess so," she sighed.

If she ever had any doubts I cleared them up and in doing so I scored major points with her. I took the initiative to cash them in. "So when was the last time you had a dick in your pussy?"

"You know the answer to that."

"I mean when was the last time you had a big dick in your pussy?" I smiled.

She returned the smile and said, "Hmm a few days after we started talking again."

"I see, I remember you telling me about how he was only good for one thing," I laughed.

"Yep," she smiled.

"You never told me what was so great about the sex." I said.

"Yes I did, I told you it was because his dick was big. I think you just wanted to hear it again," she laughed watching me play with my little dick.

"Well you never told me how big it was," I explained.

"Hmm..." She put her two finger back inside her pussy and seductively said, "It was REAL big."

I stroked slightly faster to let her know I was enjoying her words. She glanced at the tape measure on the coffee table and said, "Eight and a half inches long. Do you think that is Big?"

"Mmhmm," I whimpered while trying to hold back my orgasm.

She took her two fingers out and made sure I was watching. She then put her first three fingers in and said, "And THICK, too. Is it okay that his big dick fucked me?" she asked.

"Mmhmm."

"He fucked me so good with his huge cock."

I began to cum, messing up my second pair of boxers. She smiled happy at her achievement.

To be continued...

k4d0h1
k4d0h1
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OOAAOOAAover 11 years ago
Congratulations!!!!

Congratulations for your excellent story!!!!!!!!!!!!!!!!!!!! THX :)

AnonymousAnonymousover 13 years ago

she sounds like a real bitch. But this is still a good read.

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