The hottest conversation I ever had.
I need to provide some background for this to make sense. When I first started dating my now wife, I was 29, and she was just out of college at 23. My wife had been raised rather conservatively, being from the bible belt, and as such I was only the second guy she had ever had sex with. Being 29 though, I was not much more experienced than her. I was a late bloomer, having lost my virginity at 26. I have always had confidence problems, which led to me perpetually being friend-zoned. By the time I had met her, I had had 2 one-night stands, and 2 relationships; the first lasting for over a year, and the second only lasting about 2 months.
All throughout our dating and engagement, she never wanted to talk about her ex. All I knew was: they had dated for a couple of months, and he had taken her virginity. Whenever I tried to get her to open up more, she would say simply that she didn’t want to talk about it. She only ever elaborated slightly, saying that it had been a difficult time in her life, and she didn’t want to talk about it, or that she had been a different person. Never anything more.
At this point in our lives, both of us were in the military. A little more about her. Jane was from a small town of about 5000 people, as I said above, she had grown up a very conservative church every Sunday kinda girl. She had been a high school cheerleader. It was a small high school, with about 100 people in her graduating class, so she had known everyone. She had never had a boyfriend in high school, despite being a cheerleader, she had not had very much self confidence at this point in her life. She went to college on a ROTC scholarship, first because they would pay for college, and second because she thought the army would teach her some of the self-confidence that she had been missing out on. She is 5’7, 150 lbs, red hair, with blue eyes. She stayed fit because of cheerleading, then ROTC, then the Army. Despite this, she was always self-conscious about her hips; which she described as child bearing. She had a thin waist, but larger, round hips and a big butt, and larger thighs. Its weird, because she is kinda like two different people, skinny on top, big hips and thighs on the bottom. She complained to me at one point that she was only ever hit on by black guys. Kim Kardashian body style is what I think of. She wears a 36c bra, but her boobs don’t really seem like 36c’s to me. They seemed smaller, and not super full. When she takes the bra off, they seem to hang down a little bit, kinda like you took perfect 36c’s, and just deflated slightly. She also has the tiniest nipples and areola that I have ever seen on a girl. We met while she was at her first duty station about a year and a half after her graduation.
I am 5’11, 170lbs now, buzzed blond hair, and I’m not gonna lie, balding; with blue eyes. I try to stay in shape as well, though don’t mistake that for thinking I am ripped. I finally discovered marital arts about 2 months before I met Jane, but I don’t have a 6 pack or anything. I could stand to put on some muscle. I had struggled with my weight most of my life, and was never really in shape until I joined the military, which forced it upon me. I didn’t really become in shape as much as I just lost a bunch of weight, having been about 200 lbs of flab when I joined. When she met me, my wife said I was too skinny at 160lbs (honestly, the marital arts were great cardio), and that she needed to put some meat on my bones. I am not well endowed, which I am sure is the cause of my self-confidence issues, leading to not losing my virginity until 26. Two one-night stands, and then my first real girlfriend who dumped me after just over a year (another story), a short relationship (another story), then I met Jane.
As is life for the dual military couple, after we had been dating for several months, we ended up moving apart, and had to switch to a long distance relationship. We had a good amount of sex at the beginning, and she told me she was very satisfied with our sex life. This was after a long conversation one night where I told her about my past two relationships, where both of them had told me I was the smallest in the dick department they had ever been with, the long relationship ending after she had cheated on me. Again, she wouldn’t talk about her ex, but just said she was happy with the size of my penis, and that my ex had been crazy to cheat on me.
Our sex life eventually developed. She made me wait a long time until we had sex the first time, almost 2 months. Then we went to having sex about 3 times a week. This tapered off to once a week after about the first month, and then to twice a month, then to once a month before she left. The “honeymoon period” was short lived. After we were apart, it became a weekend every other month when one of us visited, where we would have sex usually every night until one or the other left.
Stage two of our sex life happened after we had been apart for about 6 months. She had always had a sex toy; a small vibrator that she used on her clit, she complained a lot whenever she was out of batteries. About 6 months after the move, she went to a “passion party,” where the host supplies a bunch of wine to overcome inhibitions, then passes out catalogues to everyone with sex toys that they can order. After the wine, she was feeling a little loosey goosey, and texted me asking for my opinions of what she should order. First, she sent me a picture of a thin vibrator with the description; it was 5 inches long and 3 circumference, fairly thin. This was already longer than me, I clock in at 4.5 inches erect, but this one was thinner than me. It was labeled the small size, and indicated that there were options for larger ones. Asking what I thought, I lied that she didn’t have to get the small one just for my benefit.
I was conflicted about this. On the one hand, it was totally hot thinking about her using a bigger one, part of me really wanted her to get a big thick one, but at the same time, the pride in me didn’t want her to get one bigger than me. I was kinda hoping she would object, then she replied back asking if I was sure…
“Just as long as I’m not getting replaced,” I jokingly replied. Thinking she would get a medium one, or better yet, stick with the small one. I waited for a little bit, and she texted back assurances that I wasn’t going to be replaced, and a picture of the one she wanted. It was noticeably bigger: a rabbit vibrator, 7.5 inches insertable, 6 inches circumference.
“Wow, that’s a bit bigger than the last one” I replied.
“Oh, they had bigger, but none of those were vibrators, and that’s what I really wanted. I felt a little dirty ordering the biggest vibrator in the catalogue,” she texted back with a winkie face emoji.
“If you really wanted a vibrator, you should see if they have a Hitachi magic wand, its supposedly the best, at least according to the internet videos I’m sure I have never watched, and you never have to worry about batteries” I texted back a bit humorously, trying to get her off this big toy.
“Don’t act like you don’t watch porn, we barely see each other, I know I watch some when I’m in the mood. Besides, I’d rather you watch porn then go find another girl.” She responded. To my surprise, she ordered the rabbit, a buttplug, a Hitachi magic wand, and a clone a willy kit in order to take a mold of my penis and turn into a vibrator.
Our sex life was extremely vanilla. She laid down the ground rules our third time having sex. No threesomes, No tying her down, No anal, and she did NOT give oral. Final. I had eaten her out our first two sex sessions, so I asked her if she didn’t like receiving oral.
“No, I like that a lot, but its up to you. I don’t want you to feel obligated to do it, because I think blowjobs are disgusting, and degrading, and wont do it. So I don’t want to force you to do something you don’t want to do, but you seemed enthusiastic, so I didn’t want to stop you.”
So our standard sex session went like this: me eating her out to get her in the mood, and usually give her an orgasm. She would always encourage me to go down on her, and most times, the oral lasted longer than the sex. Next, I get on top, with her legs not really pulled that far apart because she said it hurt her hips me thrusting into her that way. When she was ready to be done, she would roll me over, and get on top, and just grind back on forth on me, rubbing my nipples till I came. 99 percent of the time, the only way I can cum is with her on top, and me clenching my butt cheeks while she plays with my nipples. When she is ready for me to cum, about 30 seconds of grinding and nipple play while I’m clenching, and I’m done.
She never seemed to have an orgasm through sex. I could tell when she had an orgasm through oral, but I could never tell through the actual sex, despite her claiming I got her there. I was so confused; I almost always had to ask if she had cum as she was rolling me over. She would assure me that she had, then proceed to make me cum. I started to think she was lying, so I tried an experiment. I would purposely perform poorly, not even put my whole dick in her when thrusting, basically playing just the tip, and asked her if she came. She would always say yes, no matter how bad of a performance I gave.
The buttplug was the biggest surprise, because of the flat anal refusal. “I tried it, and I didn’t like it,” was the reply one time when I brought it up. So my first hint at the previous relationship, she had done anal. I guess I could handle that, she said she didn’t like it, I could understand… The buttplug was partially explained though because of rare drunken sex with her. Occasionally when I was eating her out when she was drunk; if I was doing a good job, she would say to stick a finger in her ass. She said she liked the extra pressure, but didn’t like the thrusting that would come with anal sex. She always seemed to cum extra hard when this happened, and I loved the feeling of her ass clenching my finger. She had to be tipsy for this though, and would always swat my hand away if I tried this when she was sober.
After she got the toys, I asked her to send me a picture, the response was just the handle of the rabbit, with the rest buried to the hilt. She texted that she really liked this toy…
Our sex life changed after the new toys, phase 2. The first time we were together after she got them, I was excited to get to use them on her, then disappointed. Our session started the same way, me giving her oral, and then me on top, however she started rubbing my nipples immediately, which had become our unspoken code that she wanted me to cum. Penetrative sex at the end of phase 1 was for less than 5 minutes, this time she wanted me to cum after less than 2 minutes, a minute or so of me on top, then she rolled me over to finish me off. It was like she was in a rush.
After I finished, she pulled out the rabbit and finished herself off. I was sorely disappointed that she didn’t let me use it on her. She acted like I wasn’t even there, and I had to settle for just rubbing her legs and messaging her breasts. She spread her legs wide, and started out slowly going in and out, gradually increasing pace, the vibration on high. It really was something else watching her plunge that huge toy in and out of her pussy, especially when she pulled it out, watching her pussy lips seem to try to grab at the toy. As she got close, she was panting, and moaning, making much louder and more enthusiastic noises than with me. Soon she was really slamming it into her pussy hard and deep. “This one is going to be big!” she huffed out between thrusts. “Stick your finger in my butt, I want you to feel how hard I cum.” I was surprised because we had come straight from the airport, no drinking. I reached down and started slowly circling her butthole, using her dripping pussy juices to lube up. I was surprised how wet she was. “Hurry, stick it in, I’m so close!” I decided to be frisky, and stuck a second finger in right after the first. As soon as I did, she moaned loudly, and buried the toy to the hilt, working it up and down really getting the vibrator part on her clit. She came hard, grunting more then moaning, her toes curled, she threw her head back and her whole body shuddered. Her butthole seemed to be trying to suck my fingers deeper into it, with her body spasming in time with her butthole. The orgasm seemed to last forever, but eventually it subsided, and she collapsed exhausted pulling the slick toy out and flopping it down between us. Her pussy looked red and angry from the punishment she had just given it. She got up to go to the bathroom, and I just sat there staring at this slick toy. I don’t quite know what came over me, but I while she was in the bathroom, I picked it up and put it in my mouth. I wanted to taste her cum on the toy for some reason. The toy was huge, and it hurt my jaw opening my mouth wide enough to fit it in. I couldn’t believe how big it was compared to me. She was a little wobbly coming back to the bedroom, and declined round two when I offered. It just felt embarrassing; her wiping pussy juice off the big toy while I walked to the bathroom with my rock hard dick swaying back and forth. I had to whack off into the toilet.
That became the new routine for whenever we were together. Our sex life did pick up, having sex 2 to 3 times a day that we were together, and I was happy for that; but it seemed to be coming with a healthy dose of unintended, humiliation. I didn’t even try to make her cum anymore; I just used her to get myself off then watched the show. I would ask her occasionally if she still came with me, to which she would reply yes, but she would slip.
One time, a couple of months later, after a session with the Hitachi paired with the butt plug, she said “that second orgasm was amazing, you did great baby, I nearly shook off the bed.” You did great was a bit of a stretch, with both her holes occupied, I was relegated to rubbing her breasts, and kissing her neck. I tried to finger her pussy between the plug in her ass and the Hitachi on her clit, but she swatted my hand away. Again, I was sporting a raging hard on after all the writhing and moaning. “You mean third” I replied, inferring that the first was oral, the second with my dick, the third with the toys. “Oh yeah, 3, see, it was so good I lost count!”
This had been the first time I had seen her use the plug. She had not wanted to use the plug with me, saying she only wanted to feel me in her, but put it in after I had cum. After she had her orgasm, she pulled the plug out and set it on my chest as she got up to go pee. “Can you clean up for me?” she asked on her way out the door. The plug had a little dollop of brown on the end of it. I wiped it off with a used towel by the side of the bed, leaving a brown streak. When she came back, she was upset that I had used a ‘good towel,’ and said that it needed to be washed in the sink. She layed down on the bed and rolled over noticing my hard on, “Awe” she said in a pouty voice “Poor baby, all worked up,” she took my dick in her hand, using her thumb and two fingers to slowly jerk me, “I’m sorry honey, I couldn’t possibly go again.” She stopped and rolled over, rubbing her hands all over her, ignoring my dick. “Uh, I’m still all tingly…” Off to the bathroom I went, two chores this time: take care of my hard on, and clean her buttplug.
Enough background.
About a month before we got married, we decided to have a long distance date night where we would both make a nice dinner, drink wine, and text. We were playing a game where we were on different trivia websites, asking each other questions. I decided to turn the conversation sexy, and lied saying there was an adult category.
“When asked how many times a week they would like to have sex, a survey of 25-30 year old women said this number.” She guessed once a week, “2-3 times a week” I replied. I remembered how before she had left, our sex life was once a month. I decided to go further. “The average American penis is blank inches long.” “6 inches?” She guessed. “5.5 inches in length, 5 inches in circumference” I actually had to search for a website that said this, because I didn’t want the number to be too much larger than me, there were too many websites that said 6-6.5. That’s when the conversation turned where I wanted it to go.
“How big is yours?” She asked.
“How big do you think?” I replied
“You’re probably 6,” she responded.
“Close,” I started, “I’m 4.5 inches long.” I was on edge waiting to hear her reply.
She was silent for a minute, and then. “Are you sure, that seems a bit small?”
“The book my school gave me when I was 13 said the average size was a range, 4.5-6” (the book really did say this) “so its not small, its just on the low end of average.“
She was silent again for a minute. “You there?” I asked.
“Yeah, I was just looking at some websites, I don’t really see anywhere that says 4.5 is average, I’m wondering if that book you got meant that 4.5-6 was the average for 13 year old boys?”
I was a little dumbfounded. I didn’t really know what to say.
“What’s your circumference?”
“I don’t actually know, I’ll have to figure out a way to measure it.”
“I think you’re probably measuring wrong, we will have to check.”
“You’re welcome to it,” I replied, “you could go check the clone a willy we made.”
“Oh yeah!” She sent back. Of course, she had totally forgotten about that toy.
It had sat completely unused, with the exception of one of our anniversaries that we had spent apart. She had sent me a picture using it saying that she wished I was there. I had a sneaking suspicion that it had been the only time she had ever used it.
“Well, it looks like you did fib a little bit,” she replied back after a minute. “This is only 4.25 long, and, its just a hair under 4 in circumference.”
Suddenly, pride started kicking in…
“I remembered being a little nervous when doing it, so it might not have been ‘full size’” I replied.
“Its ok baby, size doesn’t matter anyway. You are more than enough for me, and I am very satisfied with our sex life.“
We drank a little bit more, and she was starting to get tipsy, saying that all this sex talk was getting her horny. I pressed my advantage.
“How big was your ex?“
She didn’t respond immediately, then, “I don’t really want to talk about it.”
“We are about to get married, you never talk about it. I just want to know”
“It was a really weird time in my life, I don’t like talking about it.”
“I just feel like there is this big hole there baby, I have told you everything about my sex life before you, I just want to know. I promise, this will be the only time I ever ask about it. One conversation and that’s it.”
“Ok, one conversation, that’s it. What do you want to know?”
“Was he bigger than me?” I pressed.
“I’m gonna need another drink.” She went and poured herself another glass of wine, then,
“I don’t want you to get jealous, but yes, he was bigger. But I just want you to know that I prefer you, you are everything I am looking for in a man, and I love you very much. “
“Thank you baby, really, and I’m not jealous“ I lied.“ I didn’t text for a second.
“His cock was really weird too,” she never used the word ‘cock,’ so that was kinda shocking, but I was glad she was spontaneously offering a bit more explanation. “It had a bend in it. It was honestly unattractive. Plus his balls were really dangly, and it was annoying that they would slap into me. I really prefer yours.”
“Thank you for saying you prefer mine baby, trust me, I understand. You don’t need to reassure me every time.” Then, “Which way did it bend?”
“Down”
“that’s weird… What was his name?”
“Joe, we had a lot of the same friends. I met him at a party.”
“How big was he, as big as your toy?” I asked, slightly concerned.
“No, he was bigger. Not the whole toy, but the part that goes inside, and it was thicker. When I jacked him off, I could only get my fingers to touch if I squeezed them together. I remember being able to put one hand in front of the other, with a little bit of room to still stroke him, while sucking on the head. It hurt my jaw opening my mouth that wide, I couldn’t get any more in then just the head.”
Bombshell. Not only was his cock apparently giant, but she had sucked him?
“You sucked him?”
“yeah,” I waited for more.
“that’s part of the reason why I didn’t like having sex with him, he always made me suck him, it was disgusting.”
“Tell me about sex with him.”
“For that, I’m going to need to open a second bottle, hold on, I’ll be right back.“
I couldn’t believe that she was opening a second bottle of wine. She never drank that much.
“You’re having a second bottle?”
“Well Jodi just got home, so she is gonna share with me.” Jodi was her roommate. When she came back, “Jodi doesn’t think I should tell you, she thinks you’ll get weird if I tell you.”
“You’ve told Jodi before?”
“Yeah.”
“I promise I wont get weird” I replied.
“OK, but I want you to understand, I really didn’t enjoy sex with him. He wasn’t nice in bed the way you are. He was sweet when we first started dating, but he just got so cocky and arrogant. Our first time, I was really drunk, and I told him I was tired of being a virgin. We hadn’t even ever been on a date, but we had been to a bunch of parties together, and he would flirt with me. That night, we were at a party over Kate’s house, so we left and came back to my place. He wanted to just go to Kate’s bedroom, but I said absolutely not and made him take me home. I had planned all through high school to save myself for marriage, but I was the only virgin of all of my friends, and I was tired of listening to everyone else talk about sex and not know, plus I was drunk, so I decided it was time. Neither of us had any condoms, and I was deathly afraid of getting pregnant, so we did oral, then anal.”
“You had anal sex your first time?”
“Yeah, and oral. It was really degrading, he had me get down on my knees and suck him. He made me suck on his balls too. I hated feeling like that, with his hand on the back of my head, pushing on me. He wanted oral forever. He wasn’t even hard when I started, I didn’t realize how big he was going to get. It took him forever to get hard. When he finally did, I tried to get up but he just held me down and had me keep going. He suggested anal because we didn’t have condoms.“
I was flabbergasted at this point.
Is this why you don’t like giving oral?
“Yes” then, after a few moments, “You have to understand, I wasn’t the same person I am now. I was really naive, and I had horrible self-esteem. I had never had a real boyfriend before, and I just didn’t want to be a virgin anymore so I agreed to anal.”
“Didn’t that hurt?”
“oh yeah, the first time was really painful, and I definitely didn’t cum, you try having something that big up your butt and see if you like it. After a while I couldn’t take it anymore, and asked him to stop. He was nice enough about it, he let me finish him off with my mouth. He came so much, I choked on it, and it got all over my face and even in my hair. I didn’t do great that first time, I didn’t know what to expect. Eventually, after 2 or 3 more times, I finally had an orgasm.”
2 or 3 more times!?!?!! Did she mean anal? Not to mention, Ass to mouth?! What the Fuck?
“Like, 2 or 3 more times anal, or regular?”
“This is really embarrassing, but yes, anal, in fact I had to beg him to finally have normal sex, but he was super afraid of getting me pregnant, so we only had regular sex a handful of times, it was almost always anal. It just made sense to not risk getting pregnant. We only had regular sex because he said it was time for me to lose that virginity too, but I was so afraid of the pregnancy thing, I didn’t want him to do it at first. He said that he had had condoms break before.”
I was silent while trying to gather my thoughts, but she continued.
“It took forever for me to get used to how big he was. Honestly, he was too big, but whenever I complained about it to erin she just kept telling me how lucky I was, and that I should stick with it and eventually I would get used to it, and that he was such a catch. Eventually I figured out how to relax, and it started to become enjoyable, when I started having orgasms, the anal ones were just so powerful, that’s why I have you put a finger in there sometimes.”
“Wait, you had anal orgasms? But then why don’t you want to do anal with me?”
“See, you promised that you wouldn’t get weird.”
“I’m not being weird, I think it’s a fair question.”
“Fine, its not about you, I just don’t want to associate anything about you with him, yes I had orgasms from anal, but our relationship just got so bad. After we broke up, I swore I would never do anal ever again. There are too many bad memories associated with it.”
“What bad memories?”
“He was such a jerk, he always had to talk dirty. He would make me feel bad for having an orgasm. He would say ‘you like that big dick in your fat ass don’t you?’ He always said I had a fat ass, making me repeat it back to him. Making me beg him to fuck me harder, it was so degrading.”
“Um” I replied, but she kept going.
Whenever we were at his place, with his roommates there, he would just rub it on me and not put it in until I begged him to fuck me, loudly, so they could hear. He always called me names, and made me beg him the whole time to ‘please fuck my fat ass’, he always made me say that, ‘fuck my fat ass,’ honestly, I know you can’t see me now, but I’ve got tears streaming down my face just remembering it. It was so degrading. Whenever his roommates were there, he was just trying to show off. I would try not to cum, just to end it faster, but I just couldn’t stop myself. He would make fun of me as I came, calling me his anal slut. I hate him for what he did to me. Honestly, he was just a different person whenever his roommates were there, sweet with me alone, but showing off for them.”
I was at a loss for words, the girl I was about to marry had acted like a complete slut for her ex boyfriend.
“Wow”, I said
“I’m sorry, it’s a lot to process, and honestly, they are memories that I have tried to forget.”
“Were your orgasms with him different then they were with me?”
“Well, yes, but like I said, I prefer you.”
“Whats the difference?”
“Well, orgasms with him were just different. Like I said, I couldn’t stop myself, even if I wanted to, and trust me, I tried. What I love about you is that I don’t lose control of myself. Besides, I am living proof that a big penis is not always preferable. It was just so uncomfortable. With him I felt like I was being split in half, It always hurt at first being stretched that much, it didn’t matter if it was in my butt or my pussy, it hurt! Sometimes it hurt all the way up until right before I came, then I would just lose control of myself. Honestly I prefer your small one, with you I don’t feel like I’m being all stretched out, and you aren’t pushing into my cervix, which is really uncomfortable. I would have never stayed in that relationship as long as I did, but like I said, I had never had a boyfriend before, and at this point I was a senior in college. I was so stupid, he was just a freshman, I don’t know how he wasn’t living in the dorms, but it was a rental house that Joe’s parents owned, so I think he claimed local residency, all freshman are supposed to live in the dorms. He was so young, just a boy really, not an adult like you are. I swear, the only thing adult about him was his penis, not that I’m saying you have a boys penis, you are definitely a man, but I love that you are smaller, I wish I had known this back then. Erin kept telling me how lucky I was, how jealous she was that I had a boyfriend with a big dick, and that dirty talk was normal for guys, but it just got worse.”
“But what about with the toy, the toy is pretty big.”
“Yeah, true, but with the toy, then I am in control, and I am always warmed up from sex with you, so it doesn’t hurt when I put it in. But the big thing is that I am in control. I didn’t like to lose control and pee everywhere.”
“Wait, did you squirt with him?”
“Yeah, and I know guys think that is such a huge turn on, but trust me, its not. Its pee, and it gets everywhere. I hated when I did that with him, but he always took it as a point of pride and laughed when I did it. He knew if he fucked me really hard I would pee. He would always sit in the living room making a big deal out of the fact that I needed to change the sheets, and saying he was going to need to get a plastic liner, bragging to his roommates about it like it was something to be proud of. Its honestly disgusting. He was always bragging to his roommates about everything, I hated going over there.”
“Was it just the bragging and boasting, what do you mean it got worse?”
“I could have lived with it at this point, but yeah, it just got worse. I always had to cook for all 4 of them, so I was spending a ton of money on groceries and booze for them because none of them could buy their own. They always said they would pay me back but never did. Plus they would always barge in while we were having sex, it was like I was always on display.”
“Wait, what?”
“Well like one of them would want to borrow a book or something, so they would just open the door while we were having sex and come right in. I would try to grab a blanket and hide under it, but I know they saw me, then Joe would be like, ‘Its nothing they haven’t seen before,’ and, ‘don’t be such a prude,’ sometimes he wouldn’t even stop and let me cover up, he would just keep going despite me fighting him, and they always found some reason to linger. One time tom and joe had like a 5 minute conversation about homework, I was like, Joe STOP! We were in doggy and my boobs were just swaying around like udders. He would just slam into me harder. He was such an asshole. I asked him to have his roommates stop coming in while we were being intimate, but he just said to stop being such a prude. He never let me sleep with my clothes on, and well more then once I would wake up and be completely naked with the door standing wide open, so that any of them that walked by could see all my business.
“There was only one bathroom, the other one was broken, and they would always come in while I was taking a shower and shave or poop, I swear they were just trying to get a free show. I would cover up, as best I could, I hated taking a shower at his place, but sometimes I just didn’t have a choice. There wasn’t a shower curtain, it was just one of those stand up showers, it was regular glass too, not even frosted. Joe, would always ‘accidentally’ take the towel with him, and never bring it back even if I was screaming, so I would have to run naked to his room doing my best to cover up. One time I slipped and fell in the kitchen and twisted my ankle really bad. Shawn had to help me up and ‘accidentally’ grabbed my boob when I slipped again. Joe always made me stay completely shaved down there, so my pussy was just out on display. They were complete perverts.“
I couldn’t believe what I was hearing. This was not my fiancé at all. I couldn’t take much more. But I needed to know.
“Do you have orgasms with me?”
“Of course! I almost always have orgasms when you are licking me, and I always cum so big when we use the toys.”
“What about when we are having sex?”
“That IS sex baby, just because I don’t have an orgasm when your penis is inside of me doesn’t matter, and I have really big orgasms with the toy, better than I ever had with him. Please don’t take that as a negative, I honestly like it better this way, besides, you always cum.”
“You always said you had an orgasm with me inside of you.”
“I’m sorry, but honestly, I didn’t want to hurt your feelings. Sex feels great, and just because your penis isn’t making me cum doesn’t mean anything, our sex life is amazing. You’re not upset are you?
“No” I lied.
“Ok, now I get to ask you one.”
“Whats that?”
“Why do you always need to clench so hard to cum?”
“I don’t know, I don’t always need to do it, but I rarely cum without it, but when I clench my butt, it makes me cum every time.”
“Huh, do you think maybe you are like, squeezing your prostate?”
“I don’t know, maybe, why?”
“I was just curious, I talked about it with Jodi, and she thinks that when you are doing that you are squeezing your prostate, and that maybe something in your butt will help you cum, like it does for me.”
“Maybe” I replied a little shocked.
“Would you be willing to try?”
“uh, sure, I’ll try anything you want baby.” Thinking she was going to put a finger in my butt. Nothing wrong with a little stinky pinky.
I couldn’t believe she had been talking to her roommate about our sex life, but before I could process that.
“Lets not talk about this anymore.” She said, clearly wanting the conversation to be over. I had just one more question I needed answered.
“One more, why did you two break up?”
She took a long time responding.
“There was finally one incident, it was the straw that broke the camel’s back. We were supposed to be having a date night, alone for once. I was making dinner in the kitchen, and ran out of salt, so I had him run to the gas station down the street to get some. I decided to surprise him, so I took all my clothes off and was just wearing the apron, I was trying to be sexy. As the door opened, I leaned over the counter and told him I had a surprise waiting for him, so that he would see my butt when he came into the kitchen. I heard him come around the corner, ‘is this for me?’ I heard, and a hand grabbed my butt and stuck a finger in my pussy, but it wasn’t Joe, it was Shawn, I screamed, but Joe was right behind him laughing hysterically. I tried to turn and run to the bedroom, but Joe grabbed me and wouldn’t let me leave. He threw me over his shoulder and took me back to the kitchen. I tried to cover up, but he just ripped the apron clean off me so that I was naked. He bent me over the counter saying ‘I’m taking my surprise right here.’ I couldn’t believe what was happening. I kept yelling at him to stop, but he wouldn’t. Shawn just sat there and laughed at me struggling. I tried as hard as I could not to cum, but my body betrayed me. I couldn’t help myself. He was making me beg him to ‘fuck my fat ass harder’ right in front of Shawn. Thank god he didn’t make me do anything with Shawn, he finally started being possessive, he said ‘don’t even think about it slut, this ass belongs to me,’ when I looked over and saw shawn jacking off while he had his phone out. He filming the whole thing. I came all over the floor. Then he made me suck him off right there in the kitchen while he was giving shawn a high five. After he came, I got up to put some clothes on, and to wipe his cum off my face, and he said no, to stay like that. I refused and tried to go to the bathroom, but he just threw me over his shoulder again and took me to the living room. He then put me over his knee and proceeded to spank me. It wasn’t playful spanking either, it hurt, and I was just a sobbing mess begging him to stop. Shawn was there the whole time, and Joe just kept commenting that you needed to ‘put a woman in her place’ from time to time. He was such an asshole. My butt was bright red by the end of it, and he just left me a sobbing mess on the couch. He told shawn that you know its a good spanking when their ass is really hot, and he told him to feel how hot my ass was. I tried to cover up but Joe took the blanket away. I had to let shawn touch me, I almost threw up. I wanted to leave, but I was afraid because Joe said if I didn’t stop acting up he would get his belt. I had to finish dinner completely naked. I didn’t even eat my half of dinner Shawn ate it. I just had to wait on the two of them while the watched the video on shawn’s phone, he had taped the spanking too. Sex that night was the worst, my butt was so sore from the spanking, and he kept spanking me more asking if I had learned my lesson? After, when I tried to have a conversation with him about it, he said he was tired of how much of a prude I was, and said I should leave and not to come over anymore. He broke up with me after putting me through all of that. I nearly got in a car wreck driving home crying.”
We ended the conversation after that. I couldn’t take anymore.
I couldn’t believe everything I had just heard. It was so much. Despite that I told her I wouldn’t get weird, I was totally jealous. Everything she was saying to try and make me feel better made it worse. First, his cock just sounded enormous, then she had compared mine to a 13 year olds. She said she didn’t like feeling stretched out, and that she was glad I didn’t stretch her out, despite the fact that she liked being stretched out by her big toy. She had hated how he gave her uncontrollable orgasms, squirting orgasms, but was happy that my dick didn’t give her orgasms. She had huge orgasms from the toys, and seemed to credit that to me, but all I ever did was just rub her tits. She had had almost exclusive anal sex with him, but the most I was allowed to do was occasionally put a finger in her butt, and rarely at that. She had “always” sucked him off and even taken facials, even happy that he was such a nice guy to “let” her go ass to mouth, yet not put my dick in her mouth once. Sex always left her satisfied, while I was left to go to the bathroom and wank into the toilet. All of his roommates had seen her at her most vulnerable, either getting fucked in the ass.
What I did know though, was that I had a raging hard on from everything she had said. I wanted to see that video more than anything. She had tapped into my need to be humiliated, and I couldn’t take it. I beat my dick raw that night, knowing in my heart, that she was using that big vibrator, stretching her pussy in the ways that my little dick couldn’t, and that was exactly how she liked it.
I debated trying to get in contact with Joe or shawn and ask for the video. I’m sure they still had it, you don’t delete something like that. I spent the entire next month on websites hoping to find it uploaded.
It was a beautiful wedding, but I couldn’t help have a flash as we had our first kiss as a married couple, that she had sucked Joes fresh from her ass dick with that mouth. My heart truly dropped when right after we consummated the marriage, she got up to get the vibrator out of her suitcase.
She came quicker then usual, and I had my customary second erection. She started jacking me slowly. “Good, you’re ready for round two” she said with a sly smile. My excitement grew ”Stay here, Jodi got us a wedding present.” I lay there, comparing my hard on, to her toy, imagining Joes much bigger cock pounding her ass that was forbidden to me, wondering what was going on in the other room taking so long. She finally came back, wearing a big pink strapon. “Lets find out if it really is your prostate that’s making you cum.”
My sex life was about to enter phase 3, but that’s a story for another time.
originally published at:https://ift.tt/2LeZbAo