AFF Friends Pt. 03

Kelly and I have had a lot of fun sexting and actually fucking one time. Schedules got crazy and we couldn't get together. It was shaping up to be a beautiful Friends With Benefits situation, until she got a boyfriend.

I made her orgasm like crazy when we had sex by going down on her and fucking her. I was hoping to fuck her ass but I think she got nervous and left early. When we talked later about it she admitted she did feel nervous, and she wished she hadn't left.

We chatted and I teased her about restraining her, and having my way with her. She admitted she was a little nervous about it, and extremely turned on thinking about it.

I was 98% there talking her into meeting me after she met the boyfriend, but then she would back out. "I can't. I would feel guilty. I couldn't hurt him like that."

And in the next breath. She was turned on, wet and rubbing herself thinking about it. She wouldn't trust herself to even meet me. She didn't want to put herself in that position. She knew she would have a very hard time saying no.

So I decided to put her in that position. In the middle of the night I slipped into her driveway and put a GPS tracker on her car. When she went out to run errands, etc over the weekend I was going to be there.

Saturday morning her car started moving. We live fairly local so it was easy to grab a coffee and head out and follow her. She makes a few stops and then she stops at a local pot shop. Bingo! That's the place.

I pull up and walk in. I see her at the counter. I walk up and wrap my arms around her. I can't help contact with her big tits as I lean down and kiss her cheek. "Hi Baby Girl." I say.

She gasps and jumps. She turns her head and sees me, and almost hisses. "What are you doing here?" She asks, but never asks me to move my arms. She just holds them.

I look up at the sales girl. "You try to be nice and surprise someone with a nice kiss and a hug, and they give you the third degree." I give Kelly a squeeze and a jiggle under her tits. "She gets embarrassed by PDAs, so of course I have to hug her tight." I say with a smile.

Kelly now pulls at my arms as she realizes I am all but groping her boobs in front of the girl. Kelly gets her pot, and I have the girl throw in some edibles. I pay for it all. Kelly tries to object. I smile at the girl. "See. She is so embarrassed by a little PDA, she won't let me pay." I reach out and hand the girl my card to charge it all. I walk out with my arm around Kelly. I lead her to my car and she pauses.

"I have my car." She says a little quietly.

I lean down and kiss her softly at first, but then I hold her head by her hair and kiss her harder. She moans a little as my tongue pushes into her mouth. I break the kiss and open to door. She just looks at me. I can see the fight she is having in her head. I reach down, slip my hand into her shorts and cup my hand over her pussy. The movement is hidden by the car door. Her body stiffens and she moans. I can feel the heat and moisture through her panties.

I rub my finger up and down her lips. "You want this. Your body wants this. So get in the car." I pull out pink fluffy handcuffs from my back pocket. "Or do I have to handcuff you her and now?" I ask.

"Oh Fuck." She moans as she sits in the car.

I get in and sit beside her. I take the bag and pull out the edibles. I take out two gummies and hold them out to her. "Open your mouth." I tell her. She just looks at me. "Open your mouth, and eat the gummies, or I will cuff you and shove them down your throat Baby Girl." I say.

She opens her mouth and I pop them in her mouth. "Good Girl." I say. I put my hand on her thigh and give it a gentle squeeze up high near her crotch. "Now sit back and relax." I say and she sighs. It's a quiet ride back to my place. I close the door behind us. I put my hand at the base of her throat and pin her to the wall. I am very tall and big, and she is short so it's easy to hold her there. Her eyes go wide and she gasps as I move in and kiss her hard.

I break the kiss and stare at her. "You were a bad girl. Making Daddy wait like you did and telling him No. Daddy is going to have to punish you." I say

I can just here her breathing. "Naked Now!" I say to her firmly and I walk to the sofa. I turn and see her unhooking her bra, as she then pushes her shorts and panties off. She walks towards me. I grab her hips and turn her away from me. I grab one wrist and pull it behind her. As I do I click a cuff on her. She gasps but doesn't move. I pull back her other wrist and put the cuff on it. She moans and stands in front of me naked and handcuffed.

I pull her back and lay her over my lap. She just moans. I alternate rubbing her ass cheeks and running my fingers down her ass crack to tease her asshole and pussy. As I run my fingers down her crack she spreads her legs. I rub my index finger through her wet pussy lips. She is soaked. I slip my finger inside her pussy and she moans in pleasure. "See. I told you you wanted this. Physically and mentally you want me to have my way with you." I say as her pussy makes wet sounds with my fingering. I reach out with my free hand and spank her ass. She gasps as I do. "Admit you want me to fuck you." I say as I spank her harder.

"Oh Fuck! Yes! Yes I do. I want your big cock in me again." She gasps.

I pull my wet finger out of her pussy and slowly push it in her ass. She moans as I do. "You want my big cock here too don't you, Baby Girl?" I ask as I wiggle my finger deep in her ass.

"Oh God! Yes Daddy." She moans.

All I have to use right now is pussy juice and spit, so I will use just one finger. Once she is on my bed, her ass is getting lubed and fucked. I pull my finger around a little side the side in her asshole to stretch it some and then pull it out. With one last spank on her ass I say. "Get up and sit on the couch."

As she gets up I stand and start to strip. My dick is sticking straight out in front of me. I walk up to her. We have chatted before about me fucking her mouth like this. She looks up and me and opens her mouth. I grab a handful of hair in each hand and pull her head forward as I push in. She gags a bit as a push into the back of her mouth and throat.

I have never considered myself big, but other women have said I am a tad thick, and Kelly says I have a big cock so let's see how well she can take a good face fucking from my big cock. I hold her head and fuck away. It's amazing at first feeling her just swallow around the head of my dick as I push all the way in.

I can feel her stiffen as I push deep. She is actually drooling onto her tits, and making a ton of sexy gurgling sounds. I am a little nice and ease up, and or pull out from time to time so she can catch her breath. She is doing a great job. It feels so good. Especially as the tip of my dick pops in and out of her throat.

After a few minutes I hold her head tighter and start fucking her mouth harder, deeper and faster. She is going to make me cum, but I don't want it down her throat. I want it in her mouth and on her tongue so she can taste it.

I am so close. I pull out of her mouth and she gasps trying to catch her breath. "Open your mouth and stick out your tongue." I say as I jerk off. She instantly complies and in 3-4 strokes I groan as I cum.

My first shot hits her upper lip and lands on her tongue. My second misses her lip and lands further back on her tongue. My third is more drool as I hold my cock on her tongue. "Suck me clean and swallow it all." I say. She bends her head forward and goes right to work licking me clean.

Once she is done she pulls her mouth off me, breathes in a deep breath and lets it out. I grab her arm and pull her up. "Upstairs now!" I say as I push her towards the stairs. I hold her handcuffed hands for support as I walk her up the stairs.

I stand her at the corner of the bed and push her face down. She has one thigh on each corner of the mattress. I step over and grab the lube and the remote for the bed. I start raising the foot of the bed and Kelly's ass moves up. It lifts her up so her toes are just touching the carpet. Perfect! I slap her ass. I dribble a liberal amount of lube in her ass crack. I rub my finger around in the lube, and push it back in her ass. She lets out a small moan as my finger bottoms out in her ass. That was too easy. I pull the one finger out, put two fingers together, rub them in the lube and push them in her ass. She groans as I push two fingers in and slowly pump them in and out of her ass.

After a minute or two of finger fucking her ass with two fingers I pull my fingers out and stand to the side where she can see me. "Look at me." I say. As she looks at me I hold up the lube and pour a line down my dick. I wrap my fist around my hard dick and rub it all over. "You are about to get my big cock in your ass Baby Girl. I am going to fuck that ass and make it mine. You will never forget the first time you got your ass fucked.

Her eyes are glued to me rubbing lube into my dick, and she moans. I walk behind her and dribble more lube down her ass crack. I start from her pussy and pull my dick up between her ass cheeks covering it in lube. When I get to her ass, I pause for a moment and then push in. Her asshole holds for a moment and then I pop in her ass and she lets out a deep moan.

I push my dick slowly in her ass. Jesus Christ her asshole is tight. She lets out a long moan, but doesn't complain, ask me to stop or beg me to stop. I stay buried in her ass for a moment, and then pull back to start fucking her ass. She moans as I pull out of her ass. She groans as I push back in for the first time. "Jesus, you feel so Big." I push back in and she groans loudly. "Fuck!" She groans.

She is obviously feeling it. I have to admit her groans are turning me on, but the hot velvety vice like grip of her ass is fucking amazing. I want to feel her squeeze the tip of my dick again as I push in. I pull out, and she lets out a deep moan. I want her ass to be a fucking Slip & Slide. I squirt more lube right in her open ass. I then line back up and push back in. Her ass barely keeps me out this time. I just had to push a little harder and I push right in.

She gasps loudly. "AAAHHHH!" But again doesn't say stop or use her red/yellow code we previously chatted about. At first she is panting almost in rhythm to my fucking. "AAAHHH. AAAHHH". With a "NNGGHH". Thrown in here and there for good measure.

A funny thing happens after 2-3 minutes. Her gasps and groans of discomfort turn to sighs and moans that are definitely softer and almost pleasurable. I push in rather hard and stay buried as deep into her ass. She grunts with the hard fuck in and then gasps as I slap her ass. "Tell the truth. Do you like my big cock in your ass? Tolerate it? Or hate it?" I ask.

She is lightly panting. "At first it was so big, it kind of hurt, but I expected it to. Now as I am getting used to it, I think I like it, but you feel so big, and my ass feels so stretched." She sighs.

"So I am hearing yes Daddy I want you to fuck my ass harder." I say with an evil smile.

As I pull out she lets out a sigh. "Ooohhh." That ends in a groaning "FUCKKKK!" As I push back in hard. It am not pounding her, but I am giving her a good fucking. She would be loving it if I were fucking her pussy like this. With some of the harder, deeper strokes her moans sound more discomfort or holy shit! When I keep up a nice steady fucking the moans are definitely more enjoyable. Not to say I don't care about her pleasure. I do. I want her to thoroughly enjoy everything today so she won't be able to resist coming back, but right now I want to fuck her ass and shoot my cum in it.

I want to enjoy her tight velvety ass squeezing me so tight. I want to fuck her and listen to her sexy moans and sighs. I want to watch her ass jiggle as I fuck her. I grab the flesh on her hips in each hand, and hold her tight as I go to town fucking her ass. I am getting closer and closer to cumming. I can't help but fuck her a tad harder. The pain has left her voice now. Now there is no doubt it's a mix of pleasure and just overwhelming feelings of a cock in her ass for the first time. I can't help it. I jam in hard one last time and groan as I cum. I am jammed deep in her ass and I stay there as I cum. I can feel her ass clenching me as I stay inside her for a moment.

God that felt good. I can help relaxing and half laying against her ass as I catch my breath. After a moment she wiggles under me. "Please I need to move." She says softly.

I get off her and lower the bed. Her feet are flat on the floor and I pull her up. She balances for a moment and wiggles her hands. "Can I go to the ladies room?" She asks.

I uncuff them, and turn her to face me. "You aren't leaving. I am not done with you yet Baby Girl."

She looks at me with a mix of worry and lust. "Yes, Daddy." I turn her around and slap her ass, sending her to the bathroom. I lay back on the bed and smile with an evil thought. I hop up and grab a roll of duct tape from my closet. Out of my nightstand I grab a wand that has been in there forever. I have recently charged it in hopes of using it on her.

She comes out of the bathroom and I pat the bed. I roll over half on top of her and kiss her. She sighs as we kiss. I reach up and pinch her nipples and she sighs into our kiss. I break the kiss and lean back. I keep teasing her nipples. "So would you do anal again?" I ask.

She smiles. "Absolutely. Maybe a little slower until I am stretched out."

"So you are saying you want to have sex with me again?" I ask. I can see this sends her into a conundrum of cheating on her boyfriend. "Never mind. That's a question for another time. Right now I want to make you scream." I say as I hold up the wand.

"Oh Shit!" She says.

I pull out the tape and wrap it around the wand just under the controls. I reach down and push her legs apart. I push the buzzing end against her pussy and clit. I twist the duct tape so the adhesive isn't on her skin, and wrap the duct tape tight around her thigh. I rip it off and put a second piece lower down.

I get the cuffs and handcuff her hands together through the headboard. Now she can't pull the toy away, and she is looking worried. I stand up and I make a point of setting up my phone to record her. "No please." She sighs knowing it's a lost cause at this point. I hit record and then hit the random button on the wand. It will cycle through totally random power and vibration cycles. She gasps as it starts up.

I smile at her. "Enjoy! I need to go get a drink and wash up."

"Nooo." She moans as I walk out. As I walk out the door I hear her sigh and gasp as I hear the tone of the toy get deep. It just went to a hard vibration. I smile and walk out the door.

I stand at the kitchen sink and with some wet paper towels I wipe some of the lube off. I smile as I hear her moan. I reach for a cold bottle of water, and drink it down.

I stand there just listening for a moment. Man she likes that wand. I listen for another minute. I figure it's been about 5 minutes, so I walk back in and stand there watching. Her hips and legs are rolling and moving. Her eyes are closed and her head is rolling side to side. Her hands are holding on tight to the headboard.

She moans. "Ffuuucckkk!" And I look down at her pussy. The bed has a very large wet spot. I sit on the bed and her eyes pop open and she looks at me. "Please. Please shut it off." She begs.

"What are you going to do for me?" I ask.

She stares at me as I hear the tone of the wand slow down a bit. "Anything." She says.

"Answer me truthfully, and remember you are on candid camera." I say as I point to my phone recording her. She just moans. "Was I the first person to ever go down on you last time?" I ask.

"Yeessss." She hisses as the wand buzzes faster.

"Was I the first person to make you orgasm?" I ask.

"YES. I told you that." She sighs as her hips roll.

"Was the sex we had ok, good or the best sex you have ever had?" I ask.

"Fuck!" She sighs softly at the wand. "It was the best sex ever ok. Is that what you wanted to hear?" She almost hisses

"What I wanted was the truth. That's all. So answer me this. Did you like me fucking your face earlier?" I ask.

"Yes."

"Did you like me fucking your ass?" I ask. I see her look at the camera and then moan as the wand changes again.

"Yes, I liked getting fucked in the ass." She almost moans.

"I will stop the toy from torturing you if you promise next time to just say yes to getting together. Promise next time you won't make me chase you, Baby Girl." I say.

I can see her resolve melt. "I promise Daddy." She sighs. I reach over and click off the wand. I see her whole body slump into to bed. She kind of curls her legs and let out a sigh of relief.

I hold the tape like I am about to rip it and then stop. I look at the wet spot on the bed. "How many times did the wand make you cum?" I ask. All in all the wand was on for just shy of 10 minutes.

She sighs. "Three times."

I just smile. We have talked I know she had never orgasmed before while having sex. I am a huge breath of fresh air for her sexually. I have made her cum multiple times each time we get together, and I am not stopping just yet. I rip the tape and toss the wand aside as I climb over her. I push her legs back, rub my dick between her soaked pussy lips and push into her with one firm stroke. She lets out a deep satisfying moan.

I let out a small moan myself. Her pussy is so wet, hot, tight and soft. It's feels amazing. Feeling that soft flesh grip and rub up and down my dick as I stroke in and out. Feeling the firm ridges under the soft flesh rubbing over the head of my dick. God I love her pussy. I feel her pussy spasm and she lets out a gasping moan. That was kind of a quick orgasm. The wand must have had her close to #4. I don't stop I just keep fucking her.

I start to think I want to fuck her doggie style when I remember I still have her cuffed to the headboard. "Fuck." I sigh as I pull out of her and reach for the key. I open one cuff, and pull the cuffs through the headboard. "I am not sure we are done with these just yet." I say as I put both cuffs on one wrist for now. I stand up and look at her. "Hands and knees." I say.

She gets into position at the edge of the bed and smiles at me. "Yes Daddy." She says.

I rub my dick through her lips and push back into her pussy as I grab her hips firmly and pull her back. I start fucking her hard and fast. The only thing louder than the wet slapping is her moaning. "Uuhh. Uuhh. Uuhh." She gasps and moans with almost every stroke. Then her breathing and moan change. It gets a little deeper, and a little more animal-like. I go into overdrive and give her everything I have. "Uuggghh. Uuggg. Uuhh. Nnnngggaahhhh!" She almost screams as she cums and I can feel her juices drooling out of her.

I need a small breather. I relax my grip on her hips and she moans and falls forward. "Oh no you don't." I say as I grab her ankle and pull her to the foot of the bed. I put her ass right on the edge, and grab the bed remote. I raise the feet all the way up. I like it. Being a tall guy this puts her at almost the perfect height. Her ass is up high, her body laying down the hump in the bed. I grab her thighs and hold them as I push back in and resume fucking her.

I look down at her and I can see the sweat on her body. I am in my fifties. I haven't fucked someone sweaty in a long time. She is laying there like a limp rag doll. She is letting out little cries and moans as I give her a good fucking. It doesn't take me long after that to get that familiar feeling. I am going to cum again. I just keep going. I am sure she is going to be bruised tomorrow. I am holding the soft flesh on her hips so hard as I fuck her. After another minute or so I groan as I feel me whole core tighten up and I cum. The cramp is intense, but I let loose with one shot as I cum. That feels more like a forceful drool. I am dry and done. I haven't had sex like this in a long time, and I can't remember the last time I came 3 times.