Time to find out

You look back at Tracy and smile, but are suddenly taken aback by her current appearance. Her face is covered in her own saliva and she looks like a complete mess. Her eyeliner from work is smeared around her eyes and a strand of spit connecting her top and bottom eyelashes is even holding one of her eyes slightly closed. She truly looks like a well used whore.

Recovering from your initial surprise you finally respond "I bought you a little gift on the way home from work."

Her face lights up with a smile, head slightly tilted with curiosity as she puzzles what it might be. Deciding to finally answer her query you open the box to reveal a thick, 8 inch dildo complete with a suction cup at the base. At this reveal Tracy's eyes open wide with wonder and excitement as she sees her new toy. Tracy didn't currently have any sort of sex toys and was beaming at the potential that this new tool would bring. She practically jumps off the couch and runs round to you to inspect her new toy up close and personal.

"Thank you so much sir, I love it. But what's this part for?" she quizically asks, touching the suction cup end of the dildo.

"It's a suction cup so it can be attached to a surface. This way I can fuck you from both ends without the need for another man. Of course, we'll be getting you plenty of other real cocks soon enough, but I figure we can use this to have some fun in the mean time."

Tracy puts on a devillish grin. You're uncertain if this was brought about by the idea of being double teamed by you and a dildo or by the prospect of her being used by a host of strangers.

"I think it's time we tried out our new toy." You say as you start walking towards the window of your living room, dildo in hand and Tracy close in tow. You slap the dildo onto the glass at about waist height and turn back to Tracy, who seems a bit surprised. The reason for this astonishment, it would seem, is that your living room window is in plain view of the street. Situated up on the second floor and unobstructed from the street by any obstacles, Tracy would be in full view of the street whilst using the dildo in this position, which was exactly what you had planned.

"Well come on slut, don't you want to try out your new toy?"

"Yes of course sir, sorry sir." It seems her hesitation was simply surprisal at the lengths you were willing to go in Tracy's degradation and not due to you overstepping your bounds.

"Which end would you like to start with sir?"

"I think I'll start with your ass thanks." Tracy frowns in response. The two of you had never tried anal together before, you had done it previously with a past partner but had never popped the question to Tracy.

"I've never done that before." She responds, a look of concern on her face. Don't get me wrong, I'm eager to try, but do you mind starting a bit slower than you normally would?"

"Of course slut. I plan on using your tightest hole a lot more, wouldn't want to scare you off with your first try now would we."

With that affirmation Tracy bends over, poking her ass out to you and positions her mouth around the dildo. As she starts to bob her head up and down on her new toy, you pull a tube of lube that you picked up alongside the dildo out of your pocket. Parting her ass cheeks with your thumb and two fingers, you apply a generous amount of lube to her virgin asshole, releasing her cheeks and working it in with your finger first. You hear a soft moan come from Tracy's mouth wrapped around the dildo in front of you. After making sure to work the lube around all sides of her butthole, and applying some to your own cock, you cap the lube and rest it on the small of Tracy's back. Making sure to take your time, you slowly ease the head of your cock into Tracy's virgin ass and hear her gasp around the dildo in her mouth. She instinctively sticks her hands back towards your invasive member, although continues with the fellatio of her new plastic friend. In response, you simply grab her arms and use them as leverage to continue sliding in.

Noticing that she's holding her breath in anticipation you make sure to say "relax and focus on your breathing, the tip is the hardest part, from what I've heard."

Resuming her breathing through her nose you continue pushing the head of your cock into Tracy's behind. You finally fully insert the head of your penis and slowly begin sliding a little more of your length back and forth in her ass. Tracy starts to moan around the phallus in her other hole and you feel her body finally start to relax and release her hands, instead opting to grab her waist and use that as leverage.

You continue to slide your cock in and out of her asshole, slowly easing more and more into her and occasionally grabbing the easily accessible lube from her back and applying it to her hole. With many more slow strokes, Tracy finally manages to take your entire cock into her ass and you take a moment to let your balls rest up against her still dripping pussy.

Having reached your goal in terms of length you look into the reflection of Tracy's eyes in the window and say "Alright time to try something out. Stop actively sucking the dildo and instead, I'm going to push you onto it as I thrust into your ass."

Tracy garbles a "yesh shir" with her lips still wrapped around her new toy. With that you pull your cock almost all the way out of her ass and use your hold on her hips to pull her back off the dildo, so her lips are just barely kissing its tip. Next, you slide your cock into her ass until you finally reach the hilt and then keep pushing your hips into her, forcing her throat all the way down on the dildo. You repeat these two motions, slowly building a rhythm and increasing the pace. With her hands now free, Tracy starts massaging her pussy once again and you notice more cunt juices leaking onto your floors, she'll be cleaning her mess up later. You're now in a comfortable rhythm of fucking both her mouth and ass at the same time and have worked your way up to the same pace you'd have used on her pussy in the early days of your relationship. Tracy starts to moan around the dildo in her mouth and you're glad to hear that she's already started to enjoy anal. It's at this moment that you look up to see her reflection in the mirror and notice something in the distance.