[M]y [F]WB really starts to open me up ( part 2)

Thanks for the previous comments and suggestions. Pretty sure I can get the rest of the story out in this plus one other update.

Let’s fast forward a little bit. It’s been 2 months since I met Gil and I’m back at her place for one of our bi weekly rendezvous. I’m in agony. The next 5 minutes are going to be a mix of pain, pleasure, begging and hopefully release. I ask if I can wear the bite gag instead of the large ball gag she normally puts in my mouth. The bite gag does less to stifle my groans but it lets me bite down hard when I come into a bout of pain.

After I put the bite gag on, I assume the position – on my hands and knees. We’ve been through this more than a dozen times so I know the routine. I spread my hips a bit so that Gil will have easy access to my backside. Not much point in having easier access to my cock as that is still locked up in the chasity cage. Hence my agony.

Gil comes back into the room naked except wearing her harness. I’m relieved to see that the small strap on she has is in place. Over the past 2 months I have been falling in love with the aura of this women. Now that I’ve gotten to know her and confide my deepest fantasies – I think she’s the hottest woman I’ve been with. I love see her ample thighs and ass swish and jiggle as she moves across the room. Her little nipples on her B cup breasts are hard and visible. I love knowing that she genuinely gets off on these sessions.

I’ve done my homework and Gil is impressed. I’ve been shaving my ass twice a week since we started and it’s smooth as silk. Already in place is the butt plug ive been wearing off and on since I saw her last. I always have my ass plugged when I come to visit her. My cock has hadn’t a release in weeks. My level of frustration is about as high as it’s going to get. I’m going to ask her if she’ll let my cock out so I can jerk off. Most of the time she’s says no. Gil hasn’t sucked my cock since the first time we got together. The only oral happening is on her at the end of our weekly visits.

Gil grabs the base of the plug that’s in me and slowly starts to pull it out. She could probably have pulled it out faster but she likes stopping at the point of the widest part of the plug is stretching me. I grimmice a bit but I’ve had this plug in and out of me for the past week so it’s not too bad. It’s a relief when it finally plops out. Out comes some more lube for her fingers and my ass. One, two then three fingers ease into me. Gil barely got one finger in when we first met. Now three seems like nothing. She says as much and chuckles as she pulls out.

I see her lining up her strapon to my hole and I ask again if I can have my cock released from its cage. She smiles that devilish look that I’ve come to known and says okay – that I’ve been a good pet but I have to let her have control. My bite gag is removed first so maybe this won’t be the hard of a session after all. Slowly the cage is taken off and the whole area is a little sore from being caged for almost 5 weeks straight. The last time I was out, Gil asked me to play the porn I was watching while I did my plug exercises. I can send you the link if you’d like. It’s a video of 5 guys in a kitchen going at it. I’ve only been watching gay porn lately as the taboo of it nearly gets me off when I’m caged up. When Gil let me out last time, I came in 10 seconds while I stroked myself watching the video in front of her. I barely got hard before I came. It’s was all together not very satisfying and very embarrassing to do so in front of Gil.

My cage is off and Gill is inside of me. I barely feel the thickness of the strap on now that I’ve been stretched so much over the past two months. This makes her smaller strapon a pleasure to take and Gil goes at me with full force. Those thick thighs and ass of hers have muscle behind them and her thrusts are aggressive. My cock has been hard this whole time and I’m leaking pre-cum as she takes me.

I’m lying on my back and it’s time to finally have a good stroke for that release I’ve waited weeks for. I go to reach to my cock and she seats my hand away. Gil tells to grab my legs and pull them back towards my head. This is very humbling and slightly embarrassing as I realize how flexible I am. I have my knees nearly at my ears. I’m totally exposed to her and I’m in bliss. My pulsating cock is pointing right at my face which makes me nervous. Gil tells me I’m a good pet and that I’ve earned my reward. Impressively, she continues her thrusts and grabs my cock with her lubbed up hand. Before I can tell her to slow down, it’s too late. My moan sounds like a true sluts calling when I shoot my load and it ends up all over my face but mostly in my mouth. I beg Gil to pound me harder as she instructs me to swallow my reward. I’m being pulverized by her cock as she wipes the cum from my face into my mouth. I greedily suck it back. I wonder if I’ve also been a slut in hiding and now I’m coming into my own.

After we’re done, we continue with our weekly ritual. My cock is locked up away again. Gill puts on the gay porn I’ve been watching for weeks now. I love seen this porn so much now I know every inch of those boys beautiful bodies. While the porn plays, I pleasure Gil with my tongue. We’ve never fucked and she tells me that it won’t happen any time soon. I haven’t had sex in weeks yet I’ve never been this horny or eager as I’ve ever been. Gil cums and my face is covered with her, she tells me that I’m coming along well.

At the end of our sessions comes the part i dred the most – new plug orientation. All of the plugs in the past are nearly the same. Smaller round tip that flairs out to the widest part at the base and then tappers off at the end to keep them stuck in place. Each plug over the past few weeks gets bigger and bigger though. This week is no exception. They call this one kong at the adult toy store and I see why – it’s almost a big as my fist and it weighs over a pound.

Gil tells me she won’t be upset if I can’t get this one in but that she will be disappointed. Hearing her say that makes me want to go beyond any measure of pain to get it in. Gil’s my friend but also my sex mentor so I want to make her proud. We get the industrial lube out, it’s the most slippery and it doesn’t break down easily. Perfect for slow, deep and wide stretches.

I take the plug and lay it face up on the ground. It’s intimidating but I’m determined. I slather a thick gob of the lube all over the plug and my ass and then I straddle the plug. I’ve learned over the past weeks how to take it slow and work with a new toy the stretches me. I slowly lower myself onto the plug and the first part goes in easily. It feels good that I’ve made it a good way through without much of a strech. I look over and Gil is watching me with anticipation. I see how wet she’s getting again.

The pain starts creeping in and I wonder how close I am to the flaired base. I’m starting to think I should quit as it’s becoming unbearable. Gil’s eyes are now closed as she’s furiously rubbing herself. I look over at the porn that’s still playing and my favourite part is now on. This handsome twink is sitting on this hunks massive cock and they’re both in ecstasy. I try to time my pushes on the plug with the hunks thrusts. Then, that magically part happens. I past the widest part and the plug slips totally into my ass. The relief from the stretching comes and I sigh in satisfaction. There’s still discomfort as the whole plug has now filled my rectum. I wonder if I’ll be able to get this out.

I’m dressed and ready to leave Gil’s place. The plug is settling in it I have to slightly waddle its so big inside of me. Gil laughs and I let her know it’s not entirely funny. We debrief how far I’ve come in the past two months. I’ve only cum twice and the second was in my mouth which I’ve swallowed. My ass is so stretched it can now take a toy so fat that only a pervert would dare try. My caged cock keeps me desperate and eager to please Gil and I fantasize about the twink in the porn I watch every day.

Next week will be much of the same. Oral for Gil till she cums. Enemas, pegging and anal stretching for me. Gil tells me my cock won’t be released until we’re finished in a few weeks time. Next week though, we won’t be coming to Gil’s place. We’re meeting up at her friend’s place. Her friend Dave ….

More to come if you’re still interested.

Source: reddit.com/r/gonewildstories/comments/75agsj/my_fwb_really_starts_to_open_me_up_part_2