Girlfriend's Brother

I dropped by my girlfriend's house on a Tuesday afternoon, though I knew she had practice during this time. Only her brother, Tim, would be home and he is a cool guy. His relationships have not been working out as he planned. His last girlfriend unceremoniously dropped him but, as my girlfriend pointed out, he was managing.

I knocked on the door and Tim answered.

"Is Christina home?" I asked him.

"Not yet. She is at cheerleader practice." He answered.

"Can I wait for her here?" I asked innocently.

"Sure." He said, letting me inside. "You want a coke?"

"Thanks." I said, following him into the kitchen.

Not for the first time, I noticed how similar their body types are. They were born a few minutes apart and Tina was born first.

We were all going to the same Community College. I was working in the school garage. Tina was a cheerleader and Tim was on the swim team.

Tina encouraged me to visit her brother this afternoon. She suggested I needed to loosen up a bit and have fun-but not too much fun; she winked at me.

I really did not know what she was talking about entirely. However, I was curious to learn more about her brother's kinky activity.

I have been dating Christina a few weeks and I have been to her home several times. I met Tim more than once and noticed how similar they are in build, eye color, and wavy blonde hair.

Admittedly, I compared Tina's ass with her brother's butt, and I don't think I would be able to tell the difference by looking at them from behind!

I was thinking all this as I recalled when Tina gave me new information about Tim. I admit I was excited to learn more about her brother's kinky antics, especially after Christina gave me the go ahead to have a little fun.

After Tim let me inside their home, I was checking out his lean form in his tight blue jeans. I also wondered if it was possible for him to do what Tina told me about him.

He turned to hand me a coke and caught me checking him out.

"She told you, didn't she?" He said angrily.

I smiled broadly before answering, "Yep."

"Oh fuck! She promised me she would not tell anyone." He blurted, almost panicking.

"Relax, dude. It is okay." I reassured him. "Actually, I think it is fucking incredible-almost hot."

"You are just fucking with me." He blushed and took a sip of his own soda.

"Seriously! Ever since she told me, I have been curious as hell." I said in a serious tone.

"Curious about what? You ever try it?" He seemed to be checking if I was messing with him.

"I am not that flexible! I don't have the body type." I said to him while showing I am a stocky guy and not slim, like him.

He looked me up and down and shrugged his shoulders. "Yeah. I guess you are right."

"I want to see you do it!" I blurted out.

He sputtered out the soda he was drinking. "Are you fucking kidding me?"

"No." I said plainly. "I have never seen it done-live. I have watched a couple transgenders do it on the internet but never live."

Tina told me last weekend about her brother's talent, I have been checking out the internet and doing research. The special women were able to do it and it looked hot as hell. While watching them, I would also think about Tim's traits, focusing on what is most feminine about him. I wondered if I could get excited during his show.

"I am not doing it for you. No fucking way!" He said almost angrily.

"I will tell your friends." I said evenly.

"If you do, I will tell my sister and you will never see her again." He whined.

"It was her idea!" I told him. "She said it was super-hot and you were too flustered when she caught you. Tina said to me that you needed to lighten up and me watching you might help you unwind."

Tim had an embarrassed look on his face and stammered.

"Hey, look." I said to calm him down. "Your next girlfriend will think it is fucking hot. You can't get nervous around her. Think of this as practice."

"That is absurd! You just want to make fun of me." He rationalized.

"No. I am serious. Your sister was gushing how hot it is to watch. You might feel more comfortable having an audience. You don't want to be scared in front of your girlfriend, do you?" I asked.

"Your logic is crazy! I can't believe my sister encouraged you to see me do it!" He fumed.

"This is exactly what she was talking about." I said, shaking my head. "You need to be comfortable showing off your talent."

Tim was speechless.

"How can I prove to you I am not fucking with you?" I asked him.

He thought about it for a moment before asking me, "How about you show me your cock?"

"What?" I laughed.

"I think you are fucking with me and you are going to tell my friends what I did. I need some leverage so you will stay quiet." He reasoned.

"Hmm. Good point." I said while pulling out my soft cock.

"Stroke it. Make it hard." He teased.

"Now look who is fucking with who." I laughed, putting it back and zipping my fly.

Slightly annoyed, he continued. "Fine. Tell me you want to see mine."

I stated evenly, "I want to see you suck yourself off."

He had a shocked look on his face.

"Satisfied?" I asked eagerly.

"Not yet. Let's go to my room. I don't want anyone to look through the blinds or something like that." He said shakingly.

He hesitated before moving to his bedroom. "I don't believe this." He complained, looking back at my smiling face before heading slowly to his room.

I made a slight detour to his sister's room and quickly pulled out a pair of purple panties from her dresser and caught up with him in his bedroom.

He was watching his computer screen, which showed a scene with a big breasted woman giving a blowjob to a young guy.

"I need stimulation." He said, while moving around his room nervously.

His eyes caught what I was holding in my hand. "What the fuck?"

"I think you would look great in these. I also need added stimulation." I chuckled.

"I am not wearing those." He said adamantly.

"Come on. You are going to see my cock. The least you can do is wear them. Be thankful I did not bring her stockings!" I said gleefully.

He laughed. "I don't think my next girlfriend will want to see me in panties! I am not wearing them."

"Oh, come on. You might feel and look sexy." I suggested and then added, "You might even like it."

"You think I am going to be sexy for you? You are fucking nuts." He laughed again.

"I did not say you would be sexy." I defended myself. "I said maybe."

"So, me in panties, might excite you? Is that what you just said?" He laughed while shaking his ass at me. "You like this?"

I playfully slapped his ass away. "Oh, come on, just wear them."

He begrudgingly took the panties and looked at me expectantly. "Well, strip." He laughed.

"Huh?" I asked him.

"Yeah. That is the deal. You want me to wear panties. I want you naked. You will never tell on me because I will let them know you stripped naked and got hard watching me." He smiled.

I could not believe he was going to do it! I reluctantly stripped out of my clothes. My cock was getting hard thinking about the upcoming live sex show.

He stared at my growing cock. "You are a fucking perv."

"Hey. You are the one to talk!" I laughed.

"Touché`." He laughed nervously as he started taking his clothes off with his back to me.

Not for the first time, I noticed how similar his shapely butt and his shaved legs compared favorably to his sister. Their parents are athletic and slim blondes. However, his physical traits resembled his sister's slender hips and lithe body.

Naked and with his back to me, he reluctantly slid the panties along his smooth legs and over his hips.

"Turn around for me, slowly." I suggested when he was done.

"Are you fucking kidding me?" He asked, over his shoulder.

"Oh!Come on! In for a penny and all that." I said excitedly. In my mind, I was hoping for the same show the emo guys and transgenders exhibited while stripping and showing off their sleek and sexy forms.

He nervously turned slowly around. I was able to see his slim and hairless body, along with the growing bulge in those sexy panties.

"Satisfied?" He asked mockingly. His arms were wrapped together, and he stood there, facing me. His growing bulge was very apparent.

"Oh yeah!" I beamed. "I think you are too." I motioned to the now-tented panties.

His eyes followed mine and he almost paled. "I, uh, never wore them before. I am nervous."

"Your cock isn't." I laughed.

"Fuck you." He remarked, then looked down at my growing cock. "Look, who is the one to talk." He laughed while keeping his eyes glued to my hardening dick.

I blushed. "I am excited for the show!" I said, though probably not totally convinced of my own comment.

Tim slowly took his eyes off my cock and continued, "Now, if I do this, you will never speak about it again? This is over, yes?"

"Yes. Scout's honor." I promised.

He sat on the bed and we watched a different big chested broad sucking off a different guy.

"Nice video!" I added, watching him slowly rub his hard cock confined in the feminine underwear.

"I don't why it turns me on. I guess I wish I had a bimbo to suck my cock." He said while staring into the screen.

"How do the panties feel?" I asked while checking out his smooth ass cheek, thigh, and bulging lace panties.

"Fine, I guess.' He stammered. "Are you sure you want to watch me?"

"Hell, yeah!" I exclaimed.

"Okay. Give me some room." He finally said.

I moved to the side of the bed as he slid off and put himself on his back. His legs were draped on the foot of the bed and he fidgeted to get in a comfortable position on the carpeted floor.

"Can I help you?" I asked while staring lustfully at his panty covered ass.

"Just hold my legs." He said uncomfortably.

I moved to kneel next to him and did what he asked. I excitedly watched as he parted the panties to one side and his hard cock neared his lips.

"That is fucking incredible!" I encouraged him while slowly sliding my hands up and down his thigh and ass cheek.

"I said hold my legs, not feel me up!" He laughed while looking up at me, with my hardening cock inches from his face.

"Sorry, but you are so smooth." I said as a matter of fact, before slowly moving my hand to the back of his upper thigh-as instructed.

"Don't distract me. I need to concentrate." He said, stealing one last glimpse at my now-hard cock before positioning his hips and lowered his cock head once again toward his lips.

He slowly licked around the tip of his cock and the head slowly disappeared between his lips.

"Mmmm." I could hear his moans as he sucked on the head of his dick.

I slid my hand back up to his ass cheek and just held his globe between my fingers. Tina was getting me into anal sex. She loved it when I would feel, lick and tongue-fuck her hole. Tim's ass was close in size and shape. I was getting turned on watching him and feeling his ass jiggle between my fingers.

I think he sucked his cock harder feeling my touch and I excitedly watched as more of his length disappeared between his lips.

"Fucking hot! Fucking amazing!" I encouraged him and squeezed his ass harder.

He moaned again when my finger neared his hole, fingering it through his panties.

I don't know if his moan was protestation or encouragement, but I moved the panties to the side to see his clean butt hole.

He moaned again as my finger pressed against his opening. I dripped spit down to his gaping hole and slowly massaged my finger against the wetness and massaged the outside of his ring.

His hand closest to me was flailing so I daringly put it on my hard shaft. He instinctively wrapped his fingers around me and continued to self-suck.

I dribbled more spit onto his rosebud and slowly slid the tip of my finger tentatively across his opening.

He started to moan louder.It seemed he allowed more of his shaft between his lips. I was beginning to wonder if he could deep throat himself!

He put a stranglehold on my dick but continued to suck himself and attempted to thrust upward to meet my finger.

I could not help myself. His ass looked so much like his sister's. I leaned down and dipped my tongue to his opening.

He thrust his hips higher to meet my tongue and started to stroke my cock faster.

I grabbed his ass cheeks in both hands and my tongue tentatively licked around the opening.

He groaned loudly and seemed to suck himself harder.

Encouraged, I thrust my tongue inside him.

He pulled his slick member from his lips and yelled, "I am cumming!"

I pushed a finger deep in his ass and encouraged him, "Let me see you shoot in your mouth!"

I watched, fascinated, as shot after shot splashed into his mouth and on his face.

"Don't swallow!" I implored while positioning my cock to his lips and stroked it furiously.

He was motionless and simply watched my cock head as my loads of cum shot into his mouth and covered his lips, nose, and chin.

"Oh fuck! So hot! Fucking incredible!" I exclaimed while draining the last of my cum on his cheek.

He stared at me in disbelief while I rested my spent cock against his chin.

"That was totally fucking hot! You are so fucking sexy!" I said excitedly. "Let me watch you swallow."

I held his chin lightly to bring his jaws closed as he absently closed his lips together. I softly massaged his throat to coax him into swallowing our combined loads.

He was watching me with an astounded look on his face as he gulped down our cum.

I helped him reposition himself into a sitting position and looked at Tim, waiting for the rant.

"I can't believe you came in my mouth!" He said, almost angry, while wiping the cum off his face with his t-shirt.

"You have to admit it was fucking hot! You are fucking amazing!" I said while rubbing his shoulder.

He slowly turned away from me, finding his pants and I noticed he put them on over the panties.

I dressed and waited for him to finish and we walked out of his bedroom in silence.

He walked me to the door and I politely asked him, "Same time next week?"

He gave me a worried look. "I thought we were even."

I gave him a pat on the ass. "We are." I told him as I left the house. Walking to my car, I was thinking him giving me a hand job was not 'too much fun,' as my girlfriend's comment ran through my mind.

- - -

I knocked on my girlfriend's door the following week about the same time.

Tim was there to answer the door, dressed in a waist high yellow t-shirt and very tight blue jeans.

"Oh. It is you." He flippantly remarked as he turned away from the door, leaving me the opportunity to slip inside.

"I don't know what you expect from me, since you clearly know my sister is at cheerleader practice."

He continued walking toward the kitchen, not bothering to look behind him since he knew I would be following. I was glad because my eyes were practically glued to his ass. His sister and I had anal sex twice over the weekend and it felt so good to be inside her very tight hole.

"You know I would love a repeat from last week." I smoothly stated, while watching his ass sway in the tight jeans he was wearing.

"Not going to happen." He said flatly while pulling a soda from the fridge.

"Then why did you let me in?" I asked jovially.

He swished his hips as he faced me, "I want something from you. You owe me." He stated saucily.

I raised my eyebrows, "Oh. What do I owe you?"

"A blowjob." He smiled widely.

"Hmm." I said, making it seem like I was pondering his proposal.

"How about a counteroffer?" I asked.

"Like what?" His interest was clearly piqued.

"I want to watch you suck two cocks at the same time." I said evenly

He coughed into the soda can. "I am not sucking a stranger's cock - and yours!"

"Who said anything about adding a third person?" I grinned broadly.

"My cock and your cock in my mouth! At the same time?" He sputtered as a reply.

"Hell, yeah!" I eagerly responded.

"And then you will suck my cock and let me cum in your mouth!" He stated, excitedly.

"I am sure it will work out that way." I reasoned with him.

He smirked, appearing pleased with himself.

I interjected, "Unless, of course, you cum at the same time while sucking our cocks from your sweet lips and talented tongue."

"I am not cumming first!" He angrily stated.

"So, we have a deal?" I asked hopefully.

As if in answer, he turned away from me and walked to his bedroom.

Of course, I followed, and my cock was already starting to swell. I knew I could hold off beforehe could but I admit I was very anxious.

However, my resolve was waning. He kept his back to me and slowly shimmied out of those tight jeans, revealing high cut black, lace panties and his perfect ass globes were on full display. As his legs were becoming more exposed, he slowly revealed matching black lace stockings.

"Wow!" I said excitedly. "You did listen!"

"Do you like?" He said excitedly, wiggling his ass at me, and looking over his shoulder.

"Fuck yes! All you need is a bra, and some make up and you are a fucking knockout!" I gushed at him.

"In your dreams!" He laughed.

"Since last week; every day." I said while staring at his ass cheeks and sleek legs.

"Really?" He asked playfully, looking over his shoulder and slowly bending over to show more of his panty covered bottom.

"Fuck, yeah!" I replied while grabbing an ass cheek in each hand.

He abruptly pulled away and turned to me. "Not so fast." He friskily warned.

I am sure it was at this point, the game between the two of us was openly sexual.

Sitting down on his bed and massaging his hard, panty covered cock, he smiled at me and said excitedly, "It is your turn to strip!" He added while laughing, "Slowly."

"Are you serious?" I also laughed while removing my shirt.

"You told me to do it slowly last week. Why shouldn't I have a little fun?" He laughed more.

I slowly undressed and wiggled my ass for his amusement. I figured the more excited he was, the sooner he would cum.I was not going to suck his dick. I would kiss his ass-yes. Suck his cock-no.

Standing before him naked, with a semi-hard cock, I asked him if he liked the show.

He pushed his panties to the side and shook his hard cock at me. "What does this tell you?" He smiled broadly.

"Fuck! You are almost as big as I am!" I said, quite shocked. I was not checking his cock size last week. I wanted the show.

"Let's measure." Tim said while rising. He grabbed my cock and playfully pulled me toward him.

I was going to protest but he skillfully played with my ball sac as he slowly stroked my dick. Within a few strokes from his very talented soft and slim fingers, my cock was hardening.

Without looking at me, he pressed his hard cock against my now hard dick and rubbed them together with both hands.

"Maybe. Seems we are close in size." He said, with his eyes focused on our dicks. "You are a bit thicker, though."

I can't explain it but what started as a curiosity seemed to be growing into something more. I watched his slim limbs moving excitedly and his blonde hair slowly swishing side by side as we watched him giving us a hand job.

"Isn't this exciting or something?" He looked up at me with eagerness in his shining blue eyes. "I have never done this before. Have you?"

"No. This is a first for me." I replied, looking into his eyes.

"I bet you will cum first." He smiled at me.

"No way!" I replied, holding onto his neck. "We will probably cum at the same time if you keep doing what you are doing."

"I can hold it." He reassured me, stroking us harder and faster.

"Probably," I remarked, while caressing his slender shoulders. "We are dry, and the friction is outweighing the pleasure."

"I will remedy that problem." And with that comment, he leaned down and sucked on the head of my cock for a moment and then licked up and down my shaft, getting it nice and wet.