Best Friend (Bi-Sexual)

James and his friend Craig like to hang out and play video games at James's house, it became a casual thing after college to get back and let off steam. This arrangement continued even in the summer it was July and it was a really hot day 30Celsiuis not a record breaker but enough to make you want to escape the heat anyway possible. They both enjoyed the nice cold pool that James's Parents had recently put in with nice wooden decking, chairs and even a simple two room wooden shed to get drinks or changed in the changing room. But the young men are taken back when they hear James's mom Elizabeth yell from where she was sunbathing.

"James do you want to get ice-cream for all of us to enjoy?." Yelled Elizabeth James's mom.

"Mom I'm too hot and tired can't we wait a bit anyway the pool is to nice to get out of. Craig do you want something?". Said James

"Well I'm game for something anytime you know that." said Craig

Both dripping wet with tight swimming trunks walk gingerly trying not to slip on the wooden decking which is getting wetter as they continue walking to the house boys get out of the pool and walk towards the house.

"Do you want something in particular mom?" Yelled James

Elizabeth starting to feel the need to get up or move position because she was starting to dose of to sleep and she can't have that risking sunburns on her shoulders, back, ass and legs will be a massive pain and take time to heal. Elizabeth tiredly leans up and goes to grab her sunglasses to protect her from the sun's glare. As she puts them on she looks up and loses all focus on what her son was saying. As see notices the difference in bulges in the boys tight swimming trunks, Elizabeth hones in on Craig and studies his long thick bulge slightly poking out of the bottom from under his shorts. Starting to feel herself getting wet with an excitement she's never felt before she quickly snaps out of it.

"Well Craig your certainly welcome to stay over tonight and eat a full meal if you want. I might skip after all on the ice-cream."

Craig and James both nod in response and carry on tip toeing indoors, Craig taps James on his shoulder telling him come on into his bedroom.

"So what do you want to do instead of getting Ice-cream?". James says

"Dude your mom was so checking me out. I means there's no way she could tell what we really wanted to go indoors for right, she doesn't think about us in anyother way right?"

"No absolutely not she has no idea that her only son is bi-sexual."

"So you remember our deal don't you."

James remembers the deal alright James goes to his closet and grabs a old black lace panty and bra and looks for his wig today might be a blonde wig based on what Craig had just mentioned. James undresses and dresses the bra and panties tight and frame his body to really show off how feminine James was. the blonde girly wig framed a big wide eyed girly face, soft and smooth and rounded, with full lips, a hairless body, his girly curves, his flat chest and a nice bubble butt and apart from the small bugle in the front you would never ever guess the person before you was a boy.

Craig stood before James as a complete contrast to each other one was girly in looks and mentality whereas Craig was a man in every meaning of the word.

James tip toed over keeping Craig's attention on him fully and getting a little bashful about how he was looking at her, standing before him close enough to feel each others breath on one another. Excited James starts rubbing Craig's muscular his arms up and down in a jerking motion wanting to be held in his strong arms and admiring how different they both are, Craig let out a slight moan. and then grabbed James's hip and ass making James jump and yelp, as he gets manhandled smiling to himself.

"I want you now" James whispered before leaning in kissing Craig's neck and feeling his arms wrap around him tight, their bugles touching for the first time both jump in a automatic reaction to touch and also sexual excitement.

"Oh yeah James your little bugle is starting to awaken me."

"It's nothing compared to yours. But I want to play with yours so much more than mine".

"Let's play this out a little different I want you play as your mother, I really want to feel her little throat tight on my cock and to see her looking up at me. Your wig choice was a good one".

James and Craig kiss, lips touching gently a smile appeared before Craig moved his arms and started pushing James down, hands on his chest moving to his shoulders as he gets to his knees, he looked downward getting enjoyment over how keen he is to suck his big cock.

"Beg me to let you suck my cock, you silly little sissy, bitch".

James gets so excited when he speaks to him like this, putting their sexual positions in place.

"Daddy can I suck you big hard cock, pretty please".

"Good girl, go ahead and enjoy your reward start with stroking my 12 inch cock. I'm going to think of your mom little sissy as you stroke me. You know it's only a matter of time before I make her my bitch and you will get to watch every single second of it. You want to be a little cuck for your mom right boy?".

Being the cuckold that he wants to be. James settles down and gets comfortable on his knees and pulls the swimming trunks down to reveal a big cock, that bounces out, making him flinch because of a big sausage flying towards his face. James looks up and starts stroking his cock before licking and kissing his cock head his soft lips touching his soft let hard spongy cock head was always a thrill, slowly pulling is foreskin back to unveil the beast in its truest strongest form it looks scary because of how big it is, the musk hits seconds afterwards giving a hint of how horny Craig must of been knowing or guessing about his mother looking at his bugle earlier, maybe she did, or like him he is a horny young man that just needs to cum, Craig grabs James's hair and the right side of his face and guides his rock hard cock towards his mouth. Avoiding teeth and stretching his mouth wide the cockhead squeezes inside and quickly dives deep and rests inside his open mouth, feeling his hardest touching and filling up his mouth James blogs back and forth slightly and moves his tongue along the base following the veins and soft smooth skin of Craig's cock, his lips close down and envelope the cock invading his mouth. Only half way in James's mouth, cheeks and jaw begin to ache as he takes control and begins sucking his massive cock, like James loves to do.

"Oh yeah you sweet little fag so glad I get to fuck you boy. Your so much better than my girlfriend. I'm thinking of upgrading to a older one, one closer to home, maybe here right now. I am looking to become your new daddy. Keep sucking all the way base to tip you bitch, I want to deepthroat thinking of your mother. Keep going make me cum bitchboi".

James loved feeling his big cock inside his mouth and would gladly do whatever he wanted. Most of all one day hoping his bestfriend would make him his offical sissy girlfriend. James bobbed his head up and down on his friend's cock faster and faster. Wispering to himself I will get what you want I will be whatever you want, I want you to be with me.

"Bitchboi how do you feel about getting me a pair of your moms used panties or no more big cock for you fag boy."

Taking a big slurp and moving back to the tip and holding it looking up James nods in agreement before bobbing up and down on his massive cock feeling that his cock was harder now James begun stroking with one hand Craig's cock and using the other to play with his still wet ballsack from the pool.

James got his reward. Craig took over and saw in and out of his mouth harder and deeper his cock head poking James's throat hard enough to slightly make him gag. And then one powerful thrust and hold James's head was held tight in Craig's hands and his cock buried hard into his mouth began with one, two, three hard powerful spurts hitting the back of his throat making him gag and struggle to breath struggling to drink the sweet thick cum of his best friend. above him he heard grunting and from himself girly moaning of being able to make a man cum from the pleasure he could give, four, five, six more meant cum started to dribble out of his mouth. The seventh cumshot brought with it relief James wasn't held tight and was able to **** the cock out of his mouth to do a mixture of breath in heavily and also drink down some cum before letting it fall onto the floor.

James was in his own world as he recovered brining his fingers up to his mouth and chin to gather and lick the escaped cum, as his vision came back into focus from panting and heavy breathing he realised a few drops of cum on his chest and knees and a bit on the carpet, not wanting crusty carpet james quickly got down and licked my the cum from the carpet. once cleaned James sat up and leaned back his own little dick hard and **** for attention had wiggled out to one side and now sprung up from his panties.

"Are you boys ok I heard a noise. You ok James... Craig." Elizabeth asked

"I am fine miss we were just moving a few things that's all." James said panting still

Craig now lying naked on James's bed looking at the sissy he just cummed in and catching his breath back just smiled now imaging if he should expose her only son right now as a sissy fag that's addicted to big cock. He thought about it but knew he had a better chance of bedding Elizabeth with his help and not without it.

"Do you want me to put some Ice-cream now or a meal later miss?" Asked Craig

"Oh yes I will love to cook something for tonight nothing big mind you if that's ok". Replied Elizabeth from the other side of the closed bedroom door of her son's.

Both young men replied "Ok that's a good plan we will help out later with dinner looking forward to it".

Craig grabbed a bottle from James's bedside table and a tissue and handed them to James.

Whispering to him "I give you permission to jerk off I'm going to fuck and cum in your mother tonight fag whilst you just cum in a tissue like a pathetic sissy".

James took the tissue and throw the bottle to one side and grabbed his little dick between his thumb and index finger tugging his cockhead, thinking about his best friend hooking up with his mother. After a few tugs on his excited dick he aimed it towards the tissue in his other hand and cummed hard, watery cum in one, two, hard spurts followed by a weaker third spurt.

Craig laughed at seeing how quick James was and how pathetic he is. Who gets off on sucking cock in lingerie and then tugging his dick afterwards.

Craig and James had both recovered and got their swimming trunks on and went downstairs. Discovering Elizabeth with her back to house legs in the pool, tiny bikini clad her ass on the decking was very inviting and difficult not to look at. Her back slightly arched showed of how curvy woman she is. She gets up once she notices she has company.

They have a little chat acting like normal friends who hang out together and nothing more and all three get along and help with getting dinner made, eat and drink together until the sunsets. No hint of sexual want or need just a chilled fun evening.

James and Craig decide it's time to go to bed and Craig calls his parents to say he will sleep over at James's. James in the meantime managed to sneak into his mother's ensuite bathroom and find a used thong in the laundry basket, perfect for Craig to enjoy. In James's bedroom they watch some TV together James got up and changed into just a pair of panties knowing that Craig likes to go to bed with him in his girlish form trying to slowly make him a permanent sissy. Both of them started feeling a the sexual tension in the air and James got back into bed and reached under his bed moving a box that hide something Craig wanted eariler. Craig picked up the TV remote turned the sound down on the TV and threw it to the end of the bed and layed back in bed James pulled out the prize handing it over, a fresh pair of his mother's thong to Craig.

"So your slut mom likes to wear thongs. Should of figured she did. With an ass like that. Well she loved showing off in that bikini thong of hers earlier today. Luckily for me I'll be fucking that bitch tonight I don't care what you do bitch boy".

"I'll probably try to watch if that's ok".

"I thought you would say that, fag you want your mom to be fucked so much right".

"Oh yes please I'm so horny for it to happen right now".

"Why don't you just beg her right now do it while you get my cock out and stroke it a bit".

"Please Daddy fuck my Mommy, Mommy please fuck my daddy he has such a big cock you for to enjoy mommy".

What James couldn't see was Elizabeth peeping through the crack in the door looking in on the two young men. She was going to ask if they needed something. But instead she was frozen in shock as she watched James stroke a massive cock and Craig holding her thong in his hand and looking right at her begging her to come in the room and act on her son's request.

"Come on in James's milf you better get a good look at your fag son jerking this monster cock". Craig said smugly.

James jumping in fright leaped up out of bed in nothing more than his own mother's panties his own hard dick bouncing due to excited of Craig's cock but now james was in shock his heart was racing and his ears thumping. "mom... I... he... and...mom"

"Shutup sissy your mom can see what you are and what you like and she is drooling over me too right now".

"Mom... I... am sorry..." James whispered. Now covering up his hardon and near naked girly body.

Elizabeth was shocked not only at how controlling Craig was but now submissive and girly her son was and those panties if they could hide and contain his dick better she would have guessed he was a she.

"I knew you want it from earlier. I also know you saw and heard him your sissy son here sucking me off earlier today. I hope your going to act on your son's wish here. I'm ready and waiting for you suck me off right here and right now".

Elizabeth slowly moved out of the shadows and from behind the door and into the bedroom closing the door behind her she stood a second or two considering if she should do this or not. Standing in just a see-thru black nightie both young men got much harder looking at such a sexy milf who was contemplating if she should even allow them to see her near naked body now. She was getting self conscious.

"Why don't you come over here just forget about your sissy son focus on this big hard cock that wants you, I can see you want to do this, Elizabeth".

Elizabeth took the bait she stared at his cock she hadn't been with a real man since her college years before meeting and marrying James's father. She licked her lips and got hot, wet and slightly heady, remembering past times wild, fun, intense, orgasmic sex.

Walking over towards bed she then got on her knees and crawled over before sitting before Craig. He sat up in the bed and opened his legs so she was close. looking and staring at each other with desire, both were the best examples of a masculine muscular young man and a feminine curvy goddess.

Elizabeth tentatively reached out and grabbed Craig's hard cock both moaned at the touch his soft little hands explored Craig's hard veiny cock rubbing and stroking his ballsack and cock head as Elizabeth almost went into automatic and got Craig even harder for her. James fell to his knees and was at the side of his bed watching his mother give his best friend a hand job on his bed.

She slowly leaned downwards brushing her hair to one side behind her ear, getting closer she smelled his manly musk and his cocks excitement, gently she licks and kisses cock head and then up and down the shaft. licking and sucking his balls before working her way back up kissing his cock, she began to tongue his cockhead and slowly let her mouth to suck him inside and hold him making eye contact as she teased his cock with her soft big lips and tongue back and forth in and out, tasting it and using it like a lollipop.

"That's it you slut, you have stunning eyes when your looking at me like that. I have wanted this ever since high school. your my dream milf Elizabeth. Your son made a mistake having me as his best friend. I just wanted this. Unforntately I never knew your Fag son was a cock slut like you. I just imagined it was you when he offered blowjobs. Oh my god keep sucking you milf slut. Your so much better then your fag son here."

Elizabeth looks at Craig gets shy, blushes and tells him honestly.

"Tell me honestly do you want and need this big cock?".

"Oh my god, Craig its been so many years now, I love big cocks. We can can hook up here in James's room anytime. I just can't risk my husband finding out."

As Elizabeth went back to sucking Craig's cock bobbing up and down now wanting to be with a young hot big cocked man once more in her sexual life. James get's was finding it difficult now watching his mother really taking care of his best friends cock, his own ignored little dick was straining in his panties and it was hard not to jerk off to the sight he so often dreamed of seeing.

"Oh that's it you fucking milf slut good job. You cock sluts. You both needed to be dominated by a man a real big cocked man in your lives. Now you got it. I want to fuck you so badly Elizabeth I want to be inside you now."