In a fun and unexpected way

Your tongues quickly began exploring the others mouth as Green simply wrapped his arms around your neck as you placed one hand back on his bubble butt as the other stays on his chest ( were Green placed it.) letting you rub a phantom mound. After giving his ass a hard squeeze your hand ghosted over his hip to cup his swelled crotch, only to feel his hand gently guide it back to his butt. At this you end the kiss and give him a questioning look.

"I don't need the foreplay my body is yours tonight....Professor."

You raise an eyebrow at his choose of title. It wasn't a "Mistress" but the feeling was still there. He reluctantly got off my lap and rummaged though the bag, you saw a matching pink purse and some lipstick and makeup before pulling out.....a flesh colored double sided strap-on dildo. You just smiled down at the blushing Trap as you wiggle your panties off and reveal your bare pussy to him.

"Well then my little lab assistant before we set up the equipment shouldn't you get me ready first."

You lick your lips at him as you use one hand to part your lower lips for him to see your pink insides. He eyes seemed to glaze over for a second before he leaned in and started licking away, you could tell he was new at this but dame if he wasn't eager. His tongue drilling deep as he could go as he seemed to enjoying the taste, if his half drunk look was anything to go by. You ran your hand through his hair being carful not to accidentally knock off his wig and wishing it was his real hair so he could feel your fingers in his scalp. After a few more minutes you (with some effort.) pry his soaked mouth from your pussy as he looks up at you waiting to hear what you wanted next.

"Ok my little assistant, now that I'm ready, set up the equipment for me."

he quickly nodded his head as he reached on the bed for where he had placed the strap-on then after a little fiddling with the straps he slowly, almost reverently pushed one end into your pussy sliding in nice and deep before reaching behind you to hook up the straps, before again looking up at you with big doe eyes an starts jacking you of slowly.

"Like this professor Amber?"

You could feel the push and pull of the half inside you as he continued looking you in the eyes and then start rubbing his cheek against it. Even though you couldn't feel it like a guy would, the sight alone of Green doing it was a massive turn on. Before he raised his head up and then down, taking your dildo cock down his throat in one go. As he bobs up and down the fake cock giving you pleasant jolts from the half inside you so you let your pleasure known.

"Oooh that's a good GIRL, have you been practicing or are you just a natural cocksucker pro?"

His face though red from being hot and bothered (as yours no doubt are too) he didn't seem embarrassed at you comment as he slowly pulled back from the base to the tip, leaving it with a pop and then sticking out his tongue and swirls it around the crown making it nice and wet, before stopping.

"It's kind of a bit of both, I found out thanks to an accident with a banana that I don't have a gag reflex at all, and I just mirrored some things I saw on some porn Blue showed me once. Did...I do good?"

You nod down at his beaming face as you pat him on the head and stand up from the bed as you then pat the bed and say simply. "Up." The crossdressing boy wastes no time getting on his hands and knees on the bed as he looks back at you and gives his butt a wiggle. You give it a swat as you think not for the first time tonight that he might be enjoying this even more then you. As you pull down his panties to reveal his nice spank-able ass as well as his cock and balls. You spare a quick glance at a full length mirror off to the side. There you are naked except for a white bra and a shiny wet strap-on, holding the hips of a crossdressing boy who happens to be a childhood friend. If someone had told you 24 hours ago while you were giddy about finally going to be a trainer tomorrow, that THIS was how you were going to spend your first night as one. You would have beat them with a shoe and called the cops on the pervert. But now....

"Ok my little assistant, let's start our experiment: can a sexy sissy trap cum from getting butt fucked alone?"

You slowly started sliding into his virgin hole the pleasure from having your clit grinder into by the toy was enough to make you want to just thrust harder but you held off to slowly feed more toy into Green's butt. He didn't even try to hide the girly moans coming from him as you both were discovering he was a huge anal slut if just the first insertion was feeling this good to him. It felt like it took forever before you bottomed out in his....well bottom, you stand there for a second enjoying the faces Green was making before giving his butt a slap and started fucking him good. Finally as you started thrusting did the dildo half in you really start to feel good, stirring up your core as you started really picking up the pace as Green's arms gave out and you started drilling him face first into the bed. After a few more moment you start to feel an orgasm start to build but that was still a little ways off as you get an idea.

"Hiss! Dam Green. if a guy feels even half this good fucking someone then no wonder there obsessed with it all the time. I'm going to move you. Got it?"

So while still attached you lay him down and turn him onto his back (this seemed to send a thrill through him and sent a interesting jolt to you too) and spread his legs out as is started up again now with a better look at his lovable face and even his drooling cock, as you give him a big toothy grin as started fucking him as hard as you could.

"That's better. I wanted to see the look in your eyes as I fuck your ass Green. Are you loving this too?"

He stared back at you with (you swear) hearts in his eyes, his tongue hanging out as he moaned unabashedly.

"Yes! Yes! Yes! P-Professor! I love it so much<3 I can't stop moaning, your cock in my ass just feel so goooooood!~<3"

As he moaned out load he reached down with both hands clumsily dropping his skirt down over his crotch. As you wondered why, you saw a wet patch forming on it clueing you in. He had just cum from getting butt fucked alone, the skirt flip was so only his skirt needed to be cleaned later. You leaned forward making shore to press the skirt against his still twitching dick as you give him a hard kiss as you angled your thrusts, if you remember right that should hit....

"Jackpot."

You couldn't help the smile as he started moaning again as you hit his prostate. As you fuck using your hips to mash his boy G-spot you felt your end coming. You nibble on his earlobe a little as you feel his legs wrap around you as he just seamed stuck panting your name. All at once it hits you, the biggest orgasm of your life as lights seemed to go off in your closed eyelids as you hold still you'd crotch as close to meeting his ass as you can, you are only half aware of his twitching cock cuming again as you both ride the wave for awhile.

As you come to, your laying on the bed beside Green who at some point after you had pulled out had ditched the now dirty skirt most likely laying at the foot of the bed in a heap. As he hugs your side spooning you as he rests his head on your breast one leg sliding up yours and bumping the strap-one letting you know it's still there. As you finally get back your bearings you couldn't help kiss his forehead and smile.

"You know Green, I'm going to need a fake lab coat the next to we do this."