Pegged Husband

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ilsop
ilsop
354 Followers

* * *

Sasha asked me to go to a romantic dinner. The restaurant was only 10 minutes from my house, so she came by to pick me up. As I put on my tie, I chuckled a bit to myself. She had asked me out, and she was picking me up.

Sasha rang my doorbell right on time. I opened the door and was knocked back by her beauty: a simple black dress, knee-length; beautiful black ringlets of hair; and a big smile. "Hi, handsome," she said. Before I could say anything, she motioned me out. "Come on, I'm double parked."

Something about my own reaction as I opened the door and saw her struck me as odd, but I couldn't put my finger on it. Philosophy is about being aware of your own biases, as much as is possible. So I pondered. What thought had drifted through my mind that I had only very peripherally noticed?

She had reserved a table for us in the garden, which was unnecessary. Since it was late, the restaurant was nearly empty, and there was only one other couple in the garden. We barely noticed them, and they left just as we received our entrees: sea bass in garlic wine sauce. After we ordered deserts, Sasha changed the conversation.

"I've been thinking a lot about what you said to me about sex." Thank goodness we were in an empty restaurant! Oh right. Sasha planned this. Something about our moment at my door dawned on me right then: It was what I hadn't thought. While I had thought she looked incredibly sexy, I had had no thoughts of fucking her.

"I want you to know that this isn't just about sex for me. I love you," she continued. I had seen the outline of her breasts and thought they were beautiful, but I had had no thoughts of grabbing them. I had seen her shapely ass through her dress and realized she was wearing a thong or no underwear at all, but I had had no thoughts of bending her over and fucking her.

"I want to be with you. Always," Sasha said, looking right at me. I loved her. And I was not worried about the sex anymore. It did not feel odd to have Sasha take charge in bed, to undress, lick, and pour over my body. It did not feel odd to let Sasha spread my legs wide and do all the work. It did not feel odd to hear Sasha talk about ramming my ass. I realized that at the door, when I saw how sexy she was, I had thought about bending over for her.

I realized that, to me, sex had always meant: pushing the accelerator gently, and a woman pushing the brake. My fantasies had been about what I was going to get a woman to do. With Sasha, I have been the one pushing the brake. Now I knew that I wanted to be fucked. Sasha was on her knees with an open ring box. "Would you marry me?"

A plain band. My girlfriend had just proposed to me. "Yes, of course," I said, and she got up and hugged me.

Dessert broke up the conversation. I had cheesecake, with bright red raspberries, and an espresso. After we finished, I headed to the restroom. Sasha said she needed to go too. At the last second, she ducked into the men's room with me. I was going to ask her what she was doing, but she immediately started kissing me. At least the restroom was empty except for us!

Twenty seconds later, I broke it off. "I really do need to pee..." I said.

"Me, too," she said, and she strolled over to the urinal. Sasha reached under her dress, fiddled with her underwear, and then started to pee. In the urinal. She trailed off, shook a little, and readjusted her clothes. I was standing slack-jawed when she turned around. "I like knee-length dresses and skirts because it's easy to reach my underwear and pee standing up. I piss into the toilets in the ladies' loo standing up, 'cause they're too gross to touch."

"I ... I didn't realize it was physically possible for a woman to do that."

"Don't take too long, dear," and Sasha strode of the restroom.

* * *

The next day, I called my sister and told her about my engagement. She was overjoyed. "Oh my goodness, Avery! Congratulations! I didn't realize you were thinking about this. How did you propose?"

I had felt fine about Sasha proposing to me the night before, but for a moment, I felt a little embarrassed. "Um, well, it actually caught me off-guard..."

"Wait, wait. Did Sasha propose to you?" asked my sister, incredulous.

"Yes." My heart caught in my throat.

Pause. "Well, how romantic!" Ariel said, sincerely. "Tell me how it happened." And I gave her most of the details while she cooed.

"There's one more thing, Ariel. I'd like you to be the 'Best Woman' at the wedding."

"You mean, stand up next to you, carry the ring..."

"... and plan the bachelor party," I finished.

"Wow, I'd be honored. I have to admit, it'll be a little weird to go to a strip club."

"I don't know, Ariel. I don't like strip clubs much. Let's just go get drunk. Play pool or something." And seven months later, that's exactly what my twin sister, my friends, and I did.

* * *

A day after my conversation with my sister, I told Sasha.

"Oh, fiancée," I said.

"Yes, fiancé," she said.

"I talked to my sister yesterday, and she agreed to be my 'Best Woman.' "

Sasha stopped. "I really wish you had run that by me first." There was a lot of tension in her voice. "I don't like that much."

I was pissed off. "Why not?!"

"It's just bizarro."

"You know that we wouldn't be together if it weren't for my sister, right?"

Her tone eased. "No, I didn't know that."

"Why does it make you upset?"

Sasha laughed a little and wiped a tear away. "Oh, I'm a twit. Ariel's a looker, Avery."

"So are you."

"I want all eyes on me at my wedding. God, I'm being petty, aren't I?"

I thought for a long moment. "What about your bridesmaids?"

"No, I don't want her on my side. I don't know her well enough."

"That's not what I meant, Sasha. Are you worried about people staring at the bridesmaids?"

"Not really, no."

"Why not?" I asked.

"Because they wear ugly dresses. I've worn enough in my time. What's your point ..." Sasha trailed off.

"You can pick out something ugly for Ariel to wear," I said.

"I could ask her to wear a tux," she ruminated.

"Too far. But it can be plain and none too revealing." Pre-marital tranquility restored.

* * *

I decided to let Sasha peg me on our wedding night. I guess I wanted to surprise her. A few more months' wait wouldn't hurt her. And it would give me time to practice. I went online and ordered a few different size dildos. I had never seen Sasha's strap-on, but I wanted to make sure I had worked up to something large.

I practiced in my apartment alone. At first, I didn't even know where to go. I usually masturbate in the shower, but that wouldn't work. I settled on the bed, on top of the covers. I put a towel down. It all felt so deliberate and unsexy. I laid down on the bed, lubed up my smallest dildo, which was scarcely thicker than my finger, and started poking it around my crotch. My legs were flat on the bed, so my anus was underneath me. I pulled my legs up to my chest, and now I could reach my anus. And as I prodded the dildo in, I could tell immediately that the angle was wrong. Ariel once mentioned hitting the wrong angle with a tampon. I re-angled and pushed the dildo in an inch.

It didn't hurt, but it was uncomfortable. I had read that it takes time for the muscles to relax. So I waited. The muscles relaxed, and I worked the dildo in a little farther. After five minutes, I had the dildo in all the way, and I started stroking it in and out. It felt good, but I could not imagine having an orgasm from anal sex.

I kept at it for the two months until our wedding, at least one anal masturbation session a week. I kept working up in size, and eventually I did not need to begin my sessions with the smallest dildo. By the time I could take the large dildo – one and a quarter inches in diameter – I barely needed any warm-up other than my lubed fingers first. Despite vigorous thrusting during my sessions, I never came. What if being pegged just wasn't very good?

* * *

This was my frame of mind when the bachelor party rolled around, one week before the wedding. Just as I had suggested, Ariel had organized an evening of pool and intemperance. If any of my male friends had expected a night of strip clubs, they never let on any disappointment; I imagine my twin sister had brooked no guff about that. Although it was great to see all of my friends at one time, a pall had settled over me. My friends had picked up on my mood, and through the alcoholic haze, interpreted it as cold feet. The single men gave me a few "wish I had a girl to marry" lines, and the married men added their "marriage is wonderful" thoughts. Not that it made much of a difference. My friends all left, one by one, until only my sister and I remained at the bar, nursing scotches but mostly drinking water. We didn't normally smoke, but we had bummed a packet of cigarettes from my friend Steve and were enjoying them.

"You O.K.?" said my sister.

"I guess."

"Cause you don't seem O.K."

Of course I was going to unload my problems on my sister. I just wanted to preserve my dignity, but I was drunk enough that I really couldn't judge where that line was. I thought that as long as I didn't give graphic details, it would be fine. "I'm nervous."

Ariel took a drag. "Sex?"

"Yep."

She thought for a moment. "Still at an impasse?"

"No, I decided to have sex with Sasha on our wedding night." So far, this conversation was going brilliantly in my mind. I'm speaking in code, but Ariel's picking up on the meaning.

"Whoa. And you don't have any experience with, um, at all... You're a virgin," she said.

"I've been practicing," I said.

Ariel raised an eyebrow. "So how is that going?"

"Doesn't hurt, but it won't make ... doesn't feel, you know, ... awesome." I had thought about saying, "it won't make me cum," but had steered clear at the last second.

Ariel smiled the way she does when she's trying hard to keep a straight face. She is a terrible poker player. She reached over for her scotch, turning it a quarter turn like she does, took a sip, and set the glass down. The smile still sat at the corners of her mouth. Ariel finally looked up at me. "It's rare for women that intercourse alone does it, you know?" she said.

"I, um, what?"

"Despite male fantasies, most women need more direct stimulation."

"O.K." Pause. She stared at me. There was point I was supposed to be getting. "What's your point?"

"I'd assume that's the same for – "

"Got it. Right." I was trying to find a way to end this conversation.

When I had imagined Sasha on top of me, pumping in and out of me and grunting away, I had always imagined that it would of course lead to an orgasm for me. My thinking had been that once I got over my fear of penetration, the actual anal sex would be mind-blowing. Ariel had a point: it might not be.

All this went through my mind, and I looked over, and my sister had an inquisitive, concerned expression.

"Right," I said. "Good talk." And with that, I changed the topic to wedding logistics. But I did feel better.

* * *

"What about children?" I asked Sasha.

I had caught her by surprise. "Uh, I like them."

"Do you want to have them?"

"Maybe. Yes, I think," she said.

"Explain to me how that is supposed to work," I prodded.

"Well, there are turkey basters."

"You're joking." Her expression was flat. "You're not joking!"

She shook her head "no." "Look, there's more than the one way to get sperm into a uterus. Other than the one way that I can't do."

* * *

We moved in together just two weeks before the wedding. It just so happened that it was when Sasha's lease expired.

I had just dried off from the shower and was looking at myself in the mirror, deciding whether to shave. Sasha came up behind me, fully clothed, and pressed into my naked back. She was two or so inches shorter than me, so she was kissing my shoulder blades. "You have such a sexy ass, Avery." She grabbed my hips and ground her pelvis against my butt. "When do I get to fuck it?" she purred.

"How about on our wedding night?" I said.

"Oh, so traditional!" she laughed. She bent down and spread my cheeks wide. "Look at your sexy asshole, just begging for my big dick." And then she licked my anus, a big, wet, hard lick. I nearly fell over.

"Oh, shit that's great!" I moaned. I bent over a few inches to hold on to the sink. Sasha kept up her hard licking, then she tickled her tongue around.

"My husband's going give it up. Oh, just wait till you feel the tip of my cock pushing on your hole. Like this," she said, pushing a fingertip against my now-wet anus. "Then you'll be begging me to bury my whole, fat cock in you, won't you?"

I realized she needed some reassurance that I was into pegging. So I played it up. "Oh, please, Sasha, please fuck me with your finger." She didn't need to be asked twice. Her finger was knuckle-deep in a second. She started pumping in and on, and I reached down to stared rubbing my dick. I came all over the bathroom floor with a grunt. "Oh, fuck, wow, Sasha."

* * *

A week before the wedding, Sasha went on her bachelorette party. The next day, she finally woke up in the late morning, and we went out for lunch. She looked wrecked. "What happened to you? Where'd you go?"

"Strip club. Got a little drunk." She was speaking too slowly and over-enunciating.

"You see lots of men in G-strings, then, while you laid the groundwork for this impressive hangover?" I was peeved and being a jerk.

"No. Don't like other cocks. Went to see the ladies dance."

I knew the opposite of "other" cocks was not my cock. It was Sasha's cock. "You're an odd one, Sasha."

"As long as you'll continue to love me, I think I need to go barf now."

* * *

We were married in a small church at 11 am on a bright, clear Saturday morning. Neither Sasha nor I was religious, but the church's pastor was a friend of mine, and he performed the ceremony. The church was plain and simple, and we had decorated only modestly with some flowers. My sister stood beside me, in her rather unflattering outfit, plus my friend Dave. Sasha was beautiful. Her college friends, Tiffany and Amber, stood with her. The whole ceremony took less than fifteen minutes but was charming. My friend the pastor kept it short and sweet.

After the ceremony, we went into the back of the church to sign the papers. If you've ever bought a house or a car, it's laughable how little paperwork there is for a marriage. Sasha and I had decided the best solution was for only one of us to hyphenate his or her last name: either Sasha T.-S. and Avery S. or Sasha T. and Avery S.-T. Our names would look "married," but it would be very easy to deal with records too. There was no real reason to prefer either her or my last name hyphenation. So the only fair way to decide was to have the pastor flip a coin for us. Sasha T. and Avery S.-T. it was. My mom had tut-tutted before the wedding about this possibility. "Your dad would have wanted the family name to continue."

"Mom, Ariel didn't change her name when she got married. You can still convince her to give her kids the S. name." That got Mom out of my hair.

Upon signing the legal paperwork, we headed downstairs to the church's reception hall. Ariel had warned me beforehand that the food at "your wedding is for everyone else to enjoy – trust me, the bride and groom only get to cram in a few bites now and then." She was right. I was so busy talking to friends that I barely ate anything. We all got drunk in short order and had a lot of fun dancing. Sasha's extended family and friends were there, and they were a vivacious bunch. I've never been to a wedding that was more fun.

* * *

That evening we were on a flight to our honeymoon. We changed planes after midnight in Houston for a redeye to, eventually, Aruba. We finally got to our hotel about 9am, and we took a quick nap in our room. After, we got into swimsuits and had lunch on the beach. Sasha looked smoking hot in her suit, and I thought about kissing her, straddling her, and riding her cock. "Sasha, I know it's not our wedding night, but do you want to go do it?"

She smiled. "I thought you'd never ask!"

Once we got to our room, Sasha gave my bottom a tweak. "Get all nice and clean, stud. Use lots and lots of soap."

I didn't have an erection – I was too focused on doing this whole thing right to be turned on. When I got out of the shower, I decided to walk out of the bathroom naked. Sasha had drawn the curtains, but the midafternoon light was strong and the curtains were not thick, so the whole room had a luscious blue and green glow. Sasha was under the covers. "Come on over," she said in a seductive voice. I walked over and stood next to her, my penis only a few inches from her face. "Turn around." She squeezed my ass. Then she slid over. I lifted the covers and cuddled up to her.

Like always, she was an aggressive kisser. She was up on her elbow right away, leaning on top of me, kissing me hard and back into the pillow. She thrust her tongue in, and then she took a tour, kissing my neck and ears before returning to my mouth again. I lay back and enjoyed it. All of a sudden, she switched to licking my nipples. She gave a nice round lick to each nipple, then a little bite. I gave a sharp inhale because it felt so damn good. I would have been happy to reciprocate, but Sasha didn't really care to have her nipples played with or her breasts squeezed. She had kept her black bra on.

Sasha moved down. She spread my legs apart and gently kissed the inside of each knee. She slowly moved her kisses up my legs. The last kisses were divine, as her face sort of nuzzled in my crotch. She gently grabbed and lifted my cock and balls and started to lick my perineum. Not just soft licks. Really vigorous, left and right swipes of the tongue. "Oh my god, that's fantastic!" Sasha planted her tongue on my anus and gave it a gentle back to front lick.

"Lift up your legs," she told me. I quickly hugged my knees to my chest. She dove in, with swirling licks with the tip of her pointy tongue tracing the edge of my anus and big slurping licks that got me wet everywhere. It felt unbelievably good. Then she moved to reposition herself and something brushed against my upper thigh. Her strap-on! She'd had it on the entire time, and I hadn't realized it!

"Sasha," I said, putting my knees down, "Do you have your strap-on on?" I was looking down now and could see that she had on tight black boxer-briefs. There was a clear bulge. She moved up next to me. "Can I touch it?" I put my hand on the outside of her underwear. I could feel her giant cock. "It so big, Sasha."

"I have such a big dick. You're a lucky husband." She reached down and started to fiddle with the underwear. She opened the fly and pushed the strap-on through. It was so life-like, and so big. I rubbed my hand on it. It felt cool and rubbery, but its firmness was just right. Sasha pressed in on me, kissing me and rubbing her strap-on against me. Her underwear held it tight. It was so odd to have her strap-on poking at me and jostling against my penis. "Do you want to suck my dick?" Sasha had an inquisitive tone. She couldn't tell whether I would go for this or not, and she didn't want to force it. The idea didn't repulse me. Oh, what the hell. Why not?

I moved down. I put hand on it. Even though it wasn't real, it was disconcerting. I had never been this close to another person's penis, and even though this one was fake, it was still shocking to realize how big it was compared to my mouth. I opened up wide. It filled up my entire mouth. I gave some tentative sucks. "Jesus, that's fucking hot," Sasha panted. She thrust into my mouth. "Your tight little mouth filled with my big cock. Jesus. Want me to pump your mouth until I cum? Just fill up your mouth with my cum? I bet you'd love that." Her hand was on the back of my head. "Oh, that's it. I have to fuck you right now!" With that, she pulled the strap-on out of my mouth. She reached for the lube on the nightstand and started rubbing it on.

ilsop
ilsop
354 Followers