To boldly go where no Tobias has gone before

Prompt: Tobias is like any other guy and wants to stick it up Tris' butt.

Tris' POV

Tobias and I have been dating now for over a year. He is sweet and loving and he never asks me to do anything I don't want to. But one night, after a party at Zeke's, we came home and in his drunken state he told me that he would like to fuck my ass. I know that he would never ask me that while sober, so I never mentioned it to him.

At first I dismissed it completely. I know this is a common male fantasy and it doesn't really surprise me. It's not like our sex life is boring, but I get that he wants to try out some other stuff as well. So, while he isn't home I looked up a few videos on the porn sites to see what the fuss is all about. I know that the women in those videos are used to doing it, but I can't imagine it's not uncomfortable at least, if not even painful. And Tobias isn't exactly average to begin with. Most of the guys in those videos were okay when it came to their size, but Tobias is big, not just in length but also in width. God really blessed him. Or better yet, me. I have to admit the idea of having Tobias pound my ass isn't as appalling as it used to be. I mean it's Tobias. He would stop if I asked him too and the more I watched those videos the more intrigued I got. I researched the matter to find a way to make me more comfortable before taking him in. I even bought a butt plug to help me get used to the feeling of something in my ass. The first reaction was to push. It isn't really pleasant having something up your ass. It feels like you are constipated and therefore have the urge to push it out. But the plug I bought also vibrates. It took me a while to get used to it, but I'm now sure I could at least try with Tobias.

Tobias had to fly to New York for two days on a business trip and is coming back tonight. I make him his favorite food and decide to surprise him with making one of his fantasies a reality.

"Honey, I'm home" I hear Tobias as he enters the apartment.

"Hey, honey. Welcome back" I say and kiss him on the lips.

"I've missed you" he says holding me in his arms.

"I've missed you too" I say. "I made you lasagna and later I have a surprise for you" I say with a smirk.

"A surprise?" he asks curious.

"Yeah. Why don't you go change into something more comfortable and I serve us dinner?" I ask. He nods and kisses my lips again before picking up his duffle bag and goes into our bedroom.

After dinner he offers to do the dishes and I go into the bathroom to set everything up. I let the warm water fill the tub and set up scented candles everywhere. I prepare everything and when the tub is almost full I get rid of my clothes. The mere idea of having Tobias fuck my ass makes me wet and I wonder if I can hold back as long as I planned. But if I want to enjoy this too I need to relax first. I step out of the bathroom and find that our apartment is dark. The only light comes from our bedroom. I walk inside and find Tobias sitting on the bed with his laptop typing. The moment he sees me however he puts the laptop on the bed and hurries to me. He immediately crashes his mouth over mine and kisses me passionately. He picks me up and walks us to the bed but I pull away from his mouth.

"I prepared a bath for us" I say and he frowns. I giggle and kiss the tip of his nose.

"Can't we take a bath later?" he asks pouting.

"No, the bath is part of your surprise" I say. At that his eyes widen and he smirks. Within five minutes we are both lying in the tub relaxing and enjoying each other's company. We talk about his business trip, about the holidays and what we still need to buy to fill our fridge again. When I feel myself relaxed enough I turn around and kneel between Tobias' legs. I kiss him with all the love I feel for him, letting him know he is the only one for me. I kept telling myself I'm doing this for him, but the more I explored the matter the more I realized I wanted that too. His fantasy became my fantasy. It's dark enough in the bathroom for him not to see what I'm doing. While he has his eyes closed and kisses me, I pick up the butt plug that I hid under a towel and push it inside me. I moan a little and Tobias opens his eyes. "I want to taste you" I say. He stands up and his cock is already hard for me. I grin to myself and look up at him. I lick him thoroughly before taking him in as much as I can. I watch him closely and when he closes his eyes I turn on the vibrations of the plug. He doesn't seem to feel them, being so entranced by what I'm doing to him. I know he is close since he is getting bigger in my mouth and the thought of him coming in my ass excites me so much that I feel my own release come. I play with his balls while he entangles his fingers in my hair messing it up. Just as he comes in my mouth I come from my ass and my cries of pleasure are muffled by his still throbbing cock. I swallow his load eagerly and release him with a loud popping sound. He sighs happily as he slips back into the tub. His grin is wide but the a questioning look appears on his handsome face.

"Tris, is something vibrating?" he asks looking around. I smile shyly. Now that he is back in the tub he can feel the vibrations. I nod and he raises an eyebrow.

"Remember the party at Zeke's?" I ask and he nods. "When we came home you were drunk and you said something to me. You said you wanted us to try anal" I say and blush, but I doubt he can see that in the dimly lit room.

"Tris, I'm sorry, I…" he starts saying.

"No, don't apologize. It's okay and normal and you should never feel like you have to hide your desires from me. I love you and I would do about anything for you" I say.

"I know, babe. I love you too. But you don't have to do something you are not comfortable with" he says reassuringly.

"Thanks, but I want us to try. I went online and researched the matter" I say and feel very warm.

"You did?" he says half surprised, half amused.

"Yeah and I bought this" I say and stand up. I reach behind and pull the plug out of my ass and moan when the latex toy leaves my body. I look down at Tobias, who's jaw dropped and he stares at me.

"So, that's what I felt" he says looking from the still vibrating plug to me. He smirks. "You sure you wanna try?" he asks and stands up. I nod. "Tell me when to stop" he says and I nod again.

He pulls me to him and kisses me passionately while rubbing my sensitive clit with one hand and pinching a nipple with the other. He breaks the kiss and I turn around. I brace myself for him but to my surprise he sticks his hard cock into my pussy.

"I thought…" I say but he interrupts me.

"I want to get you hot and wet enough so that you feel comfortable" he says. He starts pounding my pussy hard and massages my boobs. I feel my pussy overflowing and when he deems I'm thoroughly aroused he pulls out and rubs his head over my asshole. Before he sticks his cock inside however he moisturizes a finger with my love juices and probes me. I moan and allow myself to relax against his touch. It's still strange and a bit uncomfortable, but it's better than before. He pumps a few times before adding a second finger and curling them a little inside me. I groan and push back against him, signaling him that I'm ready. Well, as ready as I'll ever be. He pulls out, rubs his cock against my backside a few times before slowly pushing inside me. I was right. He is huge. I feel like I'm tearing up, but at the same time I don't want him to stop. He rocks back and forth slowly to help me ease into the feeling of being filled so completely. When he is finally fully inside my ass he stops his movements. He reaches down to my pussy and inserts two fingers and starts pounding me there. He is building up my arousal again so that I relax into his touch better. He is so considerate. I'm sure most men wouldn't think of that. When my pussy is all wet again I push against him and he starts pulling out of my ass and then pushes back. The first few thrusts are slow and steady but as the heat rises in both of us he increases his pace. He lets go of my pussy and holds onto my hips to steady himself as he pounds harder and faster into my ass. I feel him swell and know he will come soon. I grab the tub with my right hand steadying myself while my left hand travels to my pussy where I stimulate my clit helping me reach my own orgasm.

"I'm close" I pant.

"Me too" he says. I can tell he is trying to hold back until I come and just as I feel my arm buckle my orgasm washes over me and I cry out his name as he empties himself for the first time into my asshole. He shouts my name, followed by a few expletives and then bends over me. Somehow we manage to sit down into the tub and I rest my back against his chest.

"That was incredible" I say.

"It was. Thank you, babe. You are the absolute best" he says and kisses my shoulder and neck. He pulls out of me and to my surprise I miss him. We'll definitely do anal again.