Never say never - 07/09/2014 (Pegger's Day)

[Something_Awesome]

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So it's late in the afternoon and the GF and I are heading home from the shop and, on the drive home, she reveals to me a fantasy she's had for a very long time. A fantasy that she has never revealed to anyone until she revealed it to me this past Wednesday (this whole story took place this past Wednesday). It was still a little surprising to me even though we were heading home to do what her fantasy involved (ironic, I guess). But let me back up a bit...

The day actually started with an argument between the GF and I. The argument actually jeopardized the plans we had for the day (plans you will know about in a moment). Luckily, the GF knows my off button (I still need to ask her to show me where that thing is) which really helps de-escalate arguments (though we seldom argue). So we're all arguing and she decides to leave the room for a couple minutes. I stay, laying on the bed on my stomach. When she comes back in to the room I make sure my face is turned away from her to make her think I'm grumpy (I wasn't upset anymore, but the point of my argument was totally valid). She jumps on my bum, presses herself against my back and whispers "I can't wait to 'F' you in the butt." (Henceforth, substitute "F" for you know what and "butt" for its more vulgar counterpart. It'll make the story more authentic; I want you to try to imagine everything as it really went down.) So we're all made up at this point, but I can't give her all the credit though as I'd like to think I am on the low end of the "stubborn spectrum." I was right though

See, the plan for this day was to go to a sex shop called Hustler Hollywood to get a strap-on harness and a dildo . For those who are not caught up, GF and I saw a pegging video while on our Vegas trip (it was an amazing scene btw) and, while I admit it did look quite hot, GF has been obsessed with pegging since the trip. The plan was for her to "'F' me in the butt."
While driving to the shop we discussed the experience we were about to have. I told her that the last time I went to Hustler was to buy her a vibrator and that they tried to pitch me some lube. I went on to say that should they try to pitch us some lube, that I was going to use that as an opportunity to say "oh, we won't be needing any. The harness and dildo isn't actually for us." The GF laughed and said "oh no you're not!" She said that she was going to tell every employee on the store floor that she was going to use the equipment on me (I know, what a 'B')! In reality, she was actually a little shy about the store visit as well. I mean, we're a hetero couple buying a strap-on. Weird, right (indulge me)?

So we get to the store and there are these women that had a lot of facial cosmetic surgery done at the indoor cafe (yes, the sex shop has a cafe). I turn to my GF and jokingly whisper something like "we've seen those women before" (y'know, because all women with facial cosmetic surgery look alike since they always seem to choose the same facial features from the catalogs). That "joke" was just a crappy attempt to hide my uneasiness about the purchase I was about to make in public view. Did I mention that this store has nothing but huge see-through glass walls facing an always-busy boulevard?

So we're just struttin' along... browsin'... totally trying to abide by the slogan on the employees' shirts: "Relax. It's just sex." We make our way to the vibrator display table (I mean c'mon, did you really think we weren't going to be all casual about our visit; that we were going to make a beeline to right to the harness and the dildos?) and starting interacting with them. An employee comes over and she shows us a lot of the couple's vibes (where the vibe goes in the female while the male is inside). There actually was one that seemed pretty awesome by a company called We Vibe (which I am considering getting now). We sort of portrayed ourselves as a couple that came for a couples vibe and the employee was totally helpful. She must have noticed something because she told us to not be shy (I honestly didn't think I was being shy though). Well, we were finally able to shoo her (employee) away and we covertly made our way to the harness and dildo section. GF starts looking at the novelty dildos (the ones that are the size of a tree and have "Proudly Made in the USA" labels on them) while I look for the harness. I found the harness (Joque harness recommended by jen1447) and the time came to look for the wand that would be the source the evening's "magic."

We spent a while looking for a dildo. An employee finally came over and said "the VixSkin dildos work best with the Joque harnesses." So I start looking through the dildos as if I am an expert and you can tell my GF is like WTF? She was wondering how the heck I was flying through dildos like I knew what I was looking for (after the employee narrowed down the brand of course). I said "babe, don't worry. The Mustang will be perfect for us." "The Mustang?" she asked. I said "yeah, the Mustang." I told her I did my research (jen1447).

After looking through every VixSkin dildo, the only Mustang I found was "vanilla" color. We were looking for a jet black color. Luckily, the employee that helped us earlier with the dildo brand passed by again. We asked her if they had any VixSkin Mustangs in jet black. She said she'd go to the back and check. While waiting for the employee, I am thinking that if there is even a 1% doubt in the minds of the people around us that the harness and dildo are not for us, then I can hold on to that 1% and play it off like I am sooo not getting my butt pounded tonight. I mean, nobody can be 100% sure about anything, right? Riiiiggghht.

So the employee came back and said that it'd take a little over a week to special order the jet black color. I told the employee that I'd think about it, so she excused herself. At this point the GF whispers to me that she is definitely not waiting to peg me. "I am doing you tonight!" She stated. I loved her enthusiasm, so we went for the "vanilla."

So we're walking up to the checkout counter (finally) to pay. As we're paying, the cashier recommends lube (duh). I tried to play it off like we did not need it and, all of a sudden, this other employee comes over (she has piercings on her cheeks) and indiscreetly proclaims "you are going to need A LOT of lube to do what you're going to do." You know that 1% I wanted to hold on to? Well, she was so convinced that the harness and dildo was for us that the 1% mental security blanket I had in my mind went flying out the window. The employee then goes on to say that I am going to need a special powder to maintain the dildo. So this dude overhears the conversation and comes over and starts debating with the chick that has the piercings on her cheeks over which powder is best for the dildo. Yep. At this point it is vividly clear to everyone that I am going to be my GF's "B" later on in the evening. Not going to lie. I started to feel like a total wuss at this point. It made me perspire a bit while they talked about the powder. It wasn't a lot of perspiration, just a little bit on the back actually. So I sort of stick my chest out and move my shoulders back (just a little bit so as to not look awkward LMAO) so that my shirt is not flush against the skin on my back. I didn't want my shirt to reveal I perspired during the purchase when I turned my back to them . I mean, "it's just sex," right?

So we're finally headed out of the store and the GF gets all giddy in the elevator. While in the car we start talking and she reveals to me a fantasy she's had for a long time that she never revealed to anyone. The fantasy is of her anally penetrating other men with a penis . A real penis. Not a strap on. Well, I didn't ask if she fantasized about using a strap on, I just assumed it was with a real penis because she said part of the fantasy involved her feeling it. In her fantasies the men are all heterosexual and she is the only one that does the penetrating. For the record, my GF is very girly and behaves very femininely, which makes her fantasy/desire to penetrate men that much more interesting (IMO). I let what she said to me marinate a little bit...

As I continued driving she had more random giddiness in the car. She was ecstatic about what she was going to do to me. As we got closer to my place I asked her if these fantasies occurred before or after she lost her virginity and she said "after." She recalls the fantasies starting at around 17 years old, so she's kept this bottled up for ten years or so (she is 27 now). Now when she expressed this fantasy, she was extremely shy about it. I think she felt overwhelmed by the fact that she was going to finally act out her fantasy and her confession just got forced out by her feeling of joy.

I could tell by her body language and face that she felt sort of like a freak. I told her that a lot of females engage in pegging and that it's pretty normal (listen to me, three months ago I would never have said it was normal LMAO). There wasn't much I could do to reassure her. Heck, I only learned what the word "pegging" meant some time after joining this site. I'm not a pegging veteran myself.

The whole thing got me thinking though... Maybe my GF needs to join a site like this one (but one tailored towards the flavor of sex that she likes) to use as an outlet to learn, understand, and cultivate (for lack of better word) her desires that are buried deep within. Desires she maybe does not even know of yet. I mean, look what WH did for me. Will probably encourage her to join one such community tomorrow.

...

I'll pick this up tomorrow morning (Sunday) guys. Much appreciation for anyone that took the time to read this and the follow-up. The follow-up will be shorter (and juicier). Any comments, questions, or insight that are posted in the meantime WILL be welcomed.

[effy2014]

I have been impressed with your openness to new things, even after expressing great reluctance. I will enjoy reading the next installment of your post.

One bit of caution . . . explore and cultivate her fantasies (and yours, for that matter) as a couple. I didn't see your involvement here as an exploration into your fantasies. You genuinely enjoy learning and you have used this site to learn and help others. The sex stuff evolved from members, especially Jen, opening your eyes and mind to alternative paths. Now that you are far more open than before you joined WH, pick up some books that interest you and explore with SAGF.

[MrB]

Great story and good on ya. Enjoy the ride 😉. Waiting on the update. I do think there is something special about a couple sharing "taboo" sexual desires. Her desires are real and you are a real man for serving your woman's needs.

[Euphoric]

SA,

So far, so good. The first time I visited a novelty store, (many years ago, lol) a great friend suggested her husband accompany me because he was familiar with the store's layout. Let me explain. At the time, we (my husband and I, and the friend and her husband) were participating in a book of sexual activities where you pull an envelope from the book, which had tailored sections for men and women. The only rule was that at some point during the week, you had to perform the activity suggested with your SO. The only indication you had before pulling the envelope was a title that coincided with the theme of said activity. I pulled an envelope that required me to use a vibrator. I didn't have one, so my friend suggested I take her husband. I'm sure my face remained an awkward shade of crimson for the first few minutes upon entering the store, but then I took the attitude that if I saw anyone I knew, then they were there for the same purpose. The employees at novelty stores are attentive and they're used to helping customers without making them like perverted freaks. I began exploring all the toys and if I wasn't sure how a toy functioned, I had no trouble asking. The employee was very accommodating and had no problem explaining and/or pulling a demo model for full effect. Let's just say by the time we left, my friend's hub knew I had a kinky side. He also offered to accompany me anytime. (The only reason I didn't take hubs was because no part of the activity was to be revealed until it actually happened.)

The first time I took hubs. along, he tried to play all cool, calm, and collected, but that's not believable when your face is flushed and your shirt is drenched from sweat He asked me about a specific item and I wasn't sure how to answer his question so I turned and asked the attendant for information. If looks could kill, I might not be here now, lol. The lady came over and began explaining the item, and different uses. She went on to explain some of the things she and her bf enjoyed. Hubs finally settled down and enjoyed browsing.

I can't wait to read the "the rest of the story."

Euphoric

[jns]

I've never been to Hustler Hollywood, but I see that they have a lot of display windows (street view) as you say. They also have parking in the rear, how appropriate. I'm sure a lot of customers like that. I did a search on the special powder. There seems to be some who think that talc can cause cancer. Choose your powder carefully. Another common power, cornstarch, can be used to to stiffen ironed shirts and create punk hair spikes. Again, somehow appropriate.

I await the next installment.

[jen1447]

Proud of you, SumSum.

[calibri~]

Have fun then. I miss hustler stores here they had some good body paints.

We have a we vibe. It looks great and all that, but I think you need to be considerate about positions because the exterior part is quite hard and can cause bruising if rammed against a not very well covered mons pubis.

[Motorguy]

Well you had my wife on edge with every word SA, So thank you for this nice story. This sure made my early Sunday morning really good if you know what i mean wink wink lol. Hey SA have you thought about writing some erotic porn. You have a future in it with all the awesome detail so thank you for that.

[Something_Awesome]

So as I mentioned (or maybe I didn't), the GF had a couple small outbursts of giggles/giddiness (told you she was girly) on the way home at the prospect of pegging me. They were random too. She could not contain the excitement. She's waited a decade (or so) to do this and probably never tried carrying out her fantasy because she thought penetrating a guy was abnormal. Guess all she needed was an implied invitation from me (lol). "I'm gonna' make my man 'take it,'" she said while in the car.

So we get to my place (I know, it's been a struggle for those of you who have survived the onslaught of my text) and open the harness first. GF wastes no time in putting it on. We got the smallest size harness and, even then, had to tighten it almost all the way. Then, out came the dildo. We tried putting it in the harness but then realized that it is easiest to install the dildo while the harness is off (stupid us).

Ok, so the dildo is actually pretty cool. I told the GF that I'd let her squeeze mine if I could squeeze hers . So we started comparing and, I gotta' tell you, it felt really authentic. You could easily tell how realistic the dildo was when you squeezed it after squeezing mine. Maybe it was because of the brand (our first time touching a dildo). The thing was over 100 bucks. For those wondering, the VixSkins Mustang is 6-1/2 inches x 1-5/8 inches (according to their site).

So it was time to start the fun. So we put a pillow, followed by a towel, under my hip and I laid on my stomach while the GF went at it with lube and one finger (this was to get me prepped). It honestly felt tight and I started having doubts about the dildo fitting even though we had done some pegging-esque experimentation in Vegas (which went well). The fact that she has small hands/fingers just added to the doubt. She finally went in with two fingers and I started to gain confidence. Then, she went in with three fingers (I wanted her to use the dildo after two fingers, but she insisted on trying to go in with three). She had a little trouble and I guess I had not noticed that I tightened my butt muscles. She reminded me to relax my butt (remember, substitute in the more vulgar version of the word). When I did that the three fingers went in real easy (remember, she also had lube). When the three fingers slid in she did this sort of breathy inhale and exhale (you know that sexy type of breathing people do during sex) and she went at it for a while. I was actually quite impressed with her restraint in using the strap-on; she took the time to get me ready with her fingers. She composed herself like a veteran of the act.

So the moment came. She squirted lube inside me (felt cold, and nice too ) and put some in her hand and stroked the dildo (I can see all this from a side-view perspective in the mirror by the way). I could see it in her face (the mirror) that she really enjoyed stroking it with lube. She finally went in...

It was actually a struggle at first. Part of it had to do with the fact that she can't feel if the dildo isn't angled correctly or if it's hitting a wall or barrier. She just feels resistance. I could feel it not being angled correctly (it was indeed hitting a wall due to its angle) but I did not guide her much. I thought the best thing to do would be for her to sort of figure it out. She tried more lube, but it did not really help her. Much did not change even when I tried to guide her. Also, part of the lack of success might have been my fault because I may have tightened my butt without noticing (I don't actually recall this with certainty, just a guess). You can sense a little bit of frustration in the GF because she hit a barrier (no pun intended) that kept her from fulfilling her fantasy.

Frustrated, she smacks one of my butt cheeks real hard (felt like she gave it her all) and told me to get on my hands and knees (I was on my stomach if you recall). She lubed back up again and went in. It was perfect this time. She was going in slowly. Very slowly. She pushed in little by little until it was all the way in (yep, took it all on the first try). Once it went all the way in she began to pull back to start thrusting. The thrusts started slow obviously and, on the first thrust she had another breathy inhale and exhale followed by a softly spoken "oh my God." She got the angling down pat in this doggy style position. The thrusts eventually picked up in pace and force. She was having an amazing time and, when she stopped to take a short break she said she was extremely wet.

After a while in the doggy position ( I can't approximate how long, but there were a few "break time" periods), I had an idea. I told her to stay in me while I go down to my stomach (I really wanted to try this position again lol). The idea worked. She was able to thrust while I was in this position without a problem. She went nuts. She looked amazingly hot too doing the humping. Her thrusts looked textbook.

I want to take this time to say that before we ever did any pegging, the GF used to play hump me every now and then. We generally had our clothes on, and it was usually just for fun and I'd get a huge laugh out of it. It started when she thought it would be funny to dry hump me, mimicking how I hump her when we're having sex. It was always good for a laugh; however, I felt like if she is going to play hump, that she might as well do it right. During these "play times" I'd actually show her how to use proper form. I tried teaching her how to hump as if it was a dance move (that's how I look at it, otherwise it just looks mechanical and clumsy). She learned very quick how to properly hump and, when I told her I was impressed, she responded by saying "of course I'd learn quick, I can Samba." The funny thing is, looking back on these play humps, that she may have been trying disguise that her play humps were actually a release for her; a way to act out her fantasy that she never told me about. Another funny thing is that these sessions served as sort of like a training for the real thing (which we never saw coming).

Going back to the pegging, I had to remind my GF to pull my hair. I say remind because she will do hair pulling during conventional sex or when I give her oral. She also said she intended to pull my hair during pegging and that she heard that pulling the guy's hair while pegging from behind opens up the guy's butt hole more. Well, after reminding her to pull my hair (did not want to remind her as it is less hot, but she was so in the zone over the pegging that she needed to be reminded multiple times) I tried to pay attention to whether my butt hole loosened. I do not feel like it actually did. In any case, the hair pulling was amazing. She has a fear of hurting me (she shouldn't because she just can't) with her aggressiveness during sex, but not today. She pulled my hair so hard that I began to feel like my hair was going to come out if she pulled any harder, and that's saying a lot because my hair is really thick. The roots shouldn't give, but I felt like they might this time. The extremely hard hair pulling signaled to me just how much she was enjoying the pegging. It felt very carnal and animalistic, and though it hurt just a tad, it was AMAZING! Pain tolerance goes way up during sex anyway.

Now there was a lot of variety going on while I was on my stomach. There was one position/angle where she had her hands on my butt cheeks while she positioned her body at a 90 degree-ish angle. Another that she did was moved in lower a bit with her hands pressed around my shoulders. My favorite was the thrusting she did with her body pressed against my back (a video we saw together was great inspiration for this one). Oh, and don't forget, there was plenty of hair pulling and dirty talk on her part (don't need to get into that on this forum though lol).

I was totally impressed with my babe's performance. I did not need to relay to her any of the thrusting guidance provided by jen. Not that I should have needed to, because I can teach any girl to thrust . If anyone needed practice, it was me. This is surprising because I thought there wouldn't be much to my role other than taking it. But my baby smacked/squeezed my butt several times reminding me to relax my butthole. I felt like I did not have total control of my butthole's ability to relax at times (weird). On the other hand, I was immensely impressed with my babe's ability to sense that my butt was not relaxed. I mean, wow? It's like pegging became second nature for her in minutes. I thought she'd be good, but not that good. She did do a lot of panting at times and would burn herself out, but that will all change with conditioning. She's a very healthy eater and in really good shape, so I'm not worried about her stamina. Even then, I was the one to suggest ending the pegging for the evening. My butt hole was starting to feel a little worn . She was so into it that I endured for as long as I could (having her stop early would have felt cruel). I don't know how long we did it for but we started when it was light out, and stopped when it became dark.

After we stopped we changed it up to more conventional forms of sex. She wasn't lying about her wetness either. It was honestly a slip n' slide in there. Looks like pegging is now going to have to be a staple in our sex diet (not too sure how I feel about this yet).

[Something_Awesome]

I hope the end does not sound rushed. If you guys need/want any extra details, feel free to ask. I tried to condense it as much as possible, especially since I promised that it'd be shorter (doesn't look like it though). But I wonder now if I did not make it as juicy as I had promised.

Also, I want to respond to a few of your posts, but I'll have to do that later tonight or tomorrow. Going to spend time with my GF shortly. And big thanks to anyone that reads! Also, MG, make sure to have your wife read my follow-up!