Two years ago, I was a single man with no anal sex experience. Two years ago, I met my future wife at my sister's wedding. Today, I am a pegged husband.
Let me start at the beginning. My sister and I are twins. As children, we were always close. Before we went to school, she was my constant playmate. Sometimes, we played Star Wars, and sometimes we played house. Once we started school, she spent time with girls, and I spent time with boys, but we still talked at home. In middle school, when puberty hit, we stayed friends. During high school, it was like having a spy on the inside. I knew which girls liked me, how girls liked to be asked out, and so on, and she got the same information from me about boys. My sister and I even ended up going to the same college. We had a shared group of friends – male and female. This may seem odd, but I preferred going out to pick up girls with my sister, not with the guys. The habits from high school had developed into a new role: she was my wingman.
So I wasn't surprised when Ariel called to tell me she was getting married. I knew she had been waiting for Tom to pop the question for several months. But I was surprised when Ariel asked me to be her "Man of Honor."
"Avery, you've always been my best friend."
It was true, and I was touched. "But you wouldn't rather ask Karen, Meghan, or Melissa?"
"Of course they'll be bridesmaids. But you and I are closer. My friends all know it. Plus, I wouldn't have met Tom if it weren't for you."
"I don't know... What does a 'Man of Honor' do? I know nothing about weddings."
"Mom's going to help me plan the wedding. What I need most is someone to talk me down when the whole thing gets overwhelming," she said, pleadingly.
"A complaints department," I inferred.
"Alright, then. I'll be your 'Man of Honor'! We're going to talk about the wedding all the time anyway. I may as well have the title. So, do I stand next to you at the altar? Wait, what do I wear?"
"Yes, next to me. You'll wear a tux. The bridesmaids' dresses will be a deep yellow ochre, so we'll get you a vest in the same color to match," she said without missing a beat.
"You just found out you were getting married. How do already know the colors?"
"Oh, I've had this planned for a long time, dear brother..."
And of course, her wedding went off without a hitch. Since our father had died, I walked Ariel down the aisle. Of course, this meant that Tom's Best Man had to come in from the side along with him. This solved the entry processional problem. We had thought of different ways to solve the exit recessional problem, but in the end, we decided that it was the least odd for the Best Man and I to process out together. Still a little odd. I just looked out at our family and her friends and ignored the dude at my side.
Ariel's wedding is where I met Sasha. She walked up and introduced herself at the reception.
"Hi, I'm Sasha. You handled the whole 'Man of Honor' thing quite smashingly."
Sasha isn't British. She just says things like "smashingly." "Thank you," I said. "I didn't do much."
"Of course you did. The bride was calm and happy."
I asked: "Are you a friend of Ariel? I thought I knew all of her friends."
"Well, your reputation is still intact. I'm a friend of Tom. From college. I used to beat him all the time in poker." This was quite the statement, since I knew Tom was quite good.
"Okay, card shark," I said, and she smiled at that, "What are the odds of four-of-a-kind in hold 'em?"
"No idea. Play the man, not the cards." Then she winked and egged me on: "Maybe that's why I know you have trouble with cards. You're thinking too much." It was my turn to smile.
We chatted about this and that, and we were really hitting it off. I couldn't get over how sexy she was: she had black hair and piercing gray eyes, and she was wearing a striking black dress that showed off her curves. I couldn't drink in enough of her beauty, her sparkling wit, and when she stood closer to me, a lovely, woodsy scent. I placed it later: sage.
Sasha's phone beeped. "That's my alarm. I have to go or I'll miss my flight."
"Where do you live?" I asked.
"Chicago." What luck!
"I live in Chicago, too – erm, Winnetka," I blurted.
"That's good. I was worried I wouldn't see you again. Let's meet soon."
"I'd love to!" I said, just a little too eagerly.
"What's your number?" she asked, phone in hand. She typed it in. Her phone beeped again. "I have to get going!" and with that, she nearly ran out the door.
My sister swung by a moment latter. "Who is that hottie?"
"One of Tom's college friends, Sasha." It was dawning on me that I didn't have her number, or a last name.
"I'd totally bang her," my sister said. My sister is totally straight. "He who hesitates, masturbates." Hanging out with her brother all the time had completely wrecked the poor girl's innocence. I left the wedding feeling somewhat dejected, a sad sack on my flight home.
However, I shouldn't have worried. Sasha called about ten days later and asked me to see a movie with her. It was a little arty for my taste, but I wouldn't have said no for any reason. I enjoyed the movie more than I thought I would.
We had coffee after.
"So you met Tom in college?"
"Yes, playing darts."
"Get out!" I said. "That's how I met Tom. I was visiting Ariel in grad school, and she had to work on a paper one night, so I went to MacGuffin's and met Tom. Then I introduced him to Ariel."
"That man was a giant on the college bar darts circuit." We laughed. He was good.
"Did you and he date?"
Sasha arched an eyebrow. "That's presumptuous, isn't it?" She laughed. "No. I just wanted to take his money in poker. He paid for a summer nice vacation one year." I could tell she wasn't exaggerating. "You and your sister are pretty close."
"Yep. Always have been."
"I heard at the wedding that Ariel used to help you pick up girls."
"Not exactly. Sort of."
"Sort of... I wonder. What secrets of our sisterhood did she give away? Did she ever dish sexy details after one of her dates?" I bumbled a bit. She laughed.
"You seem awfully curious," I said defensively.
"Mostly just nosy, but I'm also envious. I'm an only child, and it was very lonely growing up." She almost shuddered.
We talked for another two hours, late into the night. We discussed our shared love of philosophy, and our shared loathing of small dogs. We agreed upon a new slogan for Yorkie marketing: "Why not try a cat instead?"
That date led to another (shopping for a toy for her nephew), and then a third. We spent a Saturday at a fall festival, eating hot dogs and caramel apples, followed by a real dinner. And then we ended up at her apartment, on her sofa. We were kissing, but every time I made a move, she stopped me. After her third deflection, I decided the whole event was going nowhere.
"What's up?" I said. "You don't seem like the inhibited type, Sasha. I'm confused."
She seemed anxious. "Alright, honesty time," she said tentatively. "I like you, Avery. But I can't. I was, umm, sexually abused growing up."
"Oh my God. That's terrible."
"Who – "
"My stepfather. He's dead now."
"Yeah, so I can't do certain things without total panic setting in."
"What things – "
"Oral, vaginal, and anal. The thought of being penetrated is terrifying to me."
This washed over me. This woman – whom I really liked – could not have sex. I asked, "Have you been to a therapist?" and immediately thought worse of myself for asking it.
"Yep. Doesn't matter. Or, rather, it helped a great deal, in that I'm not a total basket case. But I'm never going to be able to do those things."
"Never? Not even if you love and – "
"Nope," she said. "Believe me: never. I'm sorry."
Wow. We sat in silence for a few minutes. Sasha was avoiding eye contact. I held her hand and tried to think of something comforting to say. I couldn't think of anything. I finally broke the silence by asking her, "Where does this leave us, if you can't have sex?"
"I didn't say I can't have sex. I just can't do those things." She was a bit defiant.
"What does that leave?"
"Well, I feel good about giving hand jobs, and I'm happy to receive oral sex, and..."
"That's a limited repertoire."
"And you have an anus, Avery."
"What's that supposed to mean?" The ridiculousness of my question rang in my ears for the seconds she paused before answering.
"I can stick my fingers up there, or toys."
"Toys?" I asked her, incredulous.
"I have a strap-on," she responded very matter-of-factly. I must have just gaped at her. "Now's the portion of the third date where guys go home."
Had I not been in such shock, I might have realized she was making a descriptive statement, not an imperative one. This is a path she's travelled before. While new and shocking to me, I was not the first guy on whom she'd seen the same scenario play out. Had I more presence of mind, I might have had more empathy for the abused girl who grew up to be a woman having trouble making an adult relationship work. But I'm a dolt.
"Ok. I guess I need to think. I'll call you."
"Sure," she said without conviction.
And like that, our third date was over, and I was standing outside.
What could I do? I wandered around in shock for a bit, but I'm used to talking to my sister about my girl troubles.
"Hey, bro. If you're calling me at 9:20, I'm guessing the third date didn't go well. I thought you really liked this girl."
"I do. She was sexually abused as a child."
My sister's voice went cold. "Oh my God. What happened?"
"Nothing. We were making out; I made a move; she stopped me and told me."
"So why is your date over?"
"Because she can't have sex, so she kicked me out."
"Wait, why did she kick you out? Were you a jerk?" my sister asked.
I was indignant. "No, she said, 'This is when most guys leave.' "
"You idiot! She was asking you to stay! Wait -- she put the kibosh on sex. I assume she just wanted you to stay and talk."
Rather sheepishly, I admitted, "No, she offered me a hand job, and they are obviously never good..."
"Obviously," agreed my sister.
Now for the first time, I felt awkward admitting something to my sister: "... and she offered to do me, um, anally. With a strap-on."
"Um, that's new," said Ariel.
"Exactly! I would never do that!"
Silence. "Never? If you really like this girl, maybe you should be more open-minded. I think I would try getting it up the butt," she said. I can't believe my sister talks this way!
"Totally different. You're a woman."
Silence. "What's the difference." I knew that icy tone well, but I stuck to my point.
"For women, it's just change of venue, so to speak. But for a man, it would be, well, unmanly."
"A 'change of venue'? God, you're an idiot. It's not like there's a rule that says your butt can't be an erotic zone. And if you think 'unmanly' is a negative, what do you really think of women?"
"Look, you know I respect women. I just don't want to be one in bed."
"Avery! My own brother! Sexist! Sexist!" And she hung up on me.
After another ten minutes, I realized my sister was at least right about one thing: Sasha had wanted me to stay. I picked up flowers and drove back to her house. 10:30. But the lights were on, so I knocked. Sasha looked upset when she answered the door.
"Look, I'm sorry," I said lamely. "I thought you were kicking me out."
Sasha smiled. "And yet you bring flowers, signifying guilt."
"These say, 'I wish I were a more clearheaded guy.' "
She said, "I don't need someone who stays out of guilt, or pity. I need someone who wants to be here."
"Right now, Sasha, I want to be here and end our date on a nice note. I like talking to you. Where it leads, I don't know."
"At least you're being honest."
"You were with me," I said.
"And you seem to know how to use the subjunctive. Alright, come in." There was no sex and no talk of sex that night.
* * *
After that night, our dating turned more serious. We spent lots of daytime together. She had an effortless sense of fun, seeming to find the joy or humor no matter what the situation. She was funny. And I appreciated her resolve to live life without illusions: Sasha said what she saw, whether she liked it or not.
There was some sexual play, which consisted of me going down on her, her jacking me off, or mutual masturbation. Once while she was giving me a hand job her other hand was reaching for my anus, but before she could finger me, I told her I wasn't comfortable with it. She stopped.
I couldn't say that I was fully satisfied with our sex life, but I wasn't dissatisfied either. Even though the conclusion wasn't the best, the foreplay was fantastic. There was an erotic crackle to it that I'd had with no one else. Perhaps it was that I was falling for her. Perhaps part of it was that Sasha initiated. Once, out of nowhere, she sidled up to me and started kissing me deeply. She was the more aggressive kisser, and it wasn't long before she had moved on to kissing my neck and ears, and soon after that she was after my nipples. She was an aggressive nipple-licker and pincher, and it felt great.
Then three months in, Sasha did something no girl had ever done to me. She had taken off my shirt and gone crazy on my neck and nipples, and then pulled off my underwear to rub my dick. She took off her pants, leaving her shirt and underwear on, not an uncommon arrangement for us for a finale of masturbation. All of a sudden, she pulled my legs apart and positioned herself between them. Before I could ask what she was doing, she pushed her satin-panty-covered vagina onto my perineum. She thrust her hips back and forth, rubbing me, below the penis, with her crotch. The satin provided just the right friction, and with all her moisture, it felt like a velvety tongue licking me. "Wow, Sasha, that feels awesome!"
"Yeah? It feels good when I fuck you like this?" She picked up the tempo a bit. "Yeah, I love fucking you, Avery. You're so fucking sexy, baby." To my surprise, I was close to coming. I said so, and she shouted, "Come for me!" And she started pounding me with gusto. I came onto my own chest with a grunt. As the fantastic physical sensations quieted down, the reality of what just happened hit me: my girlfriend undressed me, kissed my neck and licked my nipples, spread my legs, and thrust her crotch onto mine repeatedly, until I came. The money shot was still hot on my chest. Even though it didn't meet the technical definition, there was no other way to describe it: my girlfriend had just fucked me. And it was fucking hot.
Gone were the days of mutual masturbation. Now sex for us was her wearing those delightful satin panties and me spreading my legs. Two weeks later, she asked me to get on top. At first, it was the strangest thing I'd ever done to throw my leg over and straddle her, but she had her hands free to play with my nipples, and her up-thrusts set my taint on fire. Sasha just leered at me as she fucked me, and I realized how sexy it made me feel. Normally, guys don't feel sexy during sex; we're aroused, but we don't get to feel sexy. Now I knew what it felt like to be the object of desire, and I was hooked.
We talked about it, once. We had been sitting on the couch, and she had pulled my pants down and fucked me, holding my legs over her shoulders. Afterwards, I asked her why she liked having sex this way – as the thruster, not the recipient.
Sasha thought for a moment. "It makes me feel powerful. And strong. To spread your legs and to know I'm in control. Given my history, I need that feeling. And, your moaning is a total ego trip."
"I don't moan! I grunt."
"The hell you do. You moan." She smiled. "I love it." And with that, she clambered between my legs again, lifted them up to my chest, and fucked me again on that couch. I obliged with a lot of moaning. But I didn't have to exaggerate much.
* * *
Of course, since we had continued dating, my sister wanted to know what was going on in the bedroom. I almost thought about not telling her, and in the end I said, "We found something to do that we both enjoy." That was perhaps the awkwardest sentence I have ever uttered in my life. My sister said, "So there's no actual sex yet, umm, you know, how she asked you before?"
When I realized my sister was talking about strap-on sex as "actual sex," I replied no. My sister pressed on: "Have you thought about that anymore? Cause I bet it's pretty important to her." I was stunned. Was my sister pushing me to have strap-on sex? No: "Avery, it might blow up in your face. If you're not interested, maybe you should break it off soon."
My sister was probably right. I should probably break it off with Sasha.
* * *
I really liked Sasha. Was I really so against strap-on sex that I would not continue to see her? I could pretend that the humping was just foreplay and that I was still the man, the fucker. But if Sasha penetrated me, well, there was no denying she was the fucker, and I would obviously have to be the fuck-ee. I had no idea how relationships worked from that side. Did Sasha want me to dress up in women's clothes? Would she want to really degrading me? I watched pegging porn and read message boards. All the "you're my bitch now" stuff wasn't helping. I realized my biggest question was: If she pegged me, would she treat me any differently?
One night, I decided to strike up a conversation. After sex. So I decided to do something I hadn't done before: initiate. Sasha was watching TV from the couch, and I went upstairs to change. I pulled off my jeans and my underwear and pulled on my thin pair of pajama pants. I went back downstairs. With my heart in my throat, I croaked, "Hi, sexy," and straddled her. It was a passive way to initiate sex, which felt odd. The whole thing caught her by surprise, but she was into it. She kissed me, pulled off my shirt, and ground into my crotch. I stopped feeling odd. We came right there.
I had to do this in one swoop, like tearing off a Band-Aid. "I've been thinking about penetration..."
"I'm still not comfortable with it, but I've been thinking about it."
"What makes you uncomfortable about it?" she asked.
"It's hard to explain," I said as I searched for the words. "I worry... that you'd think less of me, you know? A man's supposed to be the strong one in a relationship, but if you use a strap-on on me, that makes me weaker than you. Would you still respect me?"
She started laughing.
"Hey, fuck you, it's not funny," I said.
"You're worried how I could respect you in the morning? You sound like a lady from the '50s"
My frustration faded away, and I had to smile, too.
"Would you want me to dress up?"
"Like in lingerie? No, I'm not into that." She smiled. "Although you have such a nice ass, you'd look good in anything, even panties."
* * *
Sasha and I had both studied philosophy in college. I asked her one day, out of idle curiosity, what had drawn her to it.
"I read a bunch of self-help books in high school, but they only ever made me feel worse about myself. You know, I could never will myself to be as positive as the books said I was supposed to be. Then one day I picked up Nietzsche. I don't really have any family, not anyone close, I mean. The 'life is emptiness and suffering' rap made my own life seem not quite so awful... What about you?"
"Me?" I asked. "You know I was mostly interested in political philosophy. But I think I liked philosophy because of its detachment. It's a way to step back from the day-to-day and just think."
Sasha just nodded.
"Plus, my mom's really overbearing," I said.
She laughed. "Now you sound like a psych major, you cheeky bastard."
* * *
Sasha got a whole lot more direct in the bedroom. She had always talked sort of dirty during sex, but now it was explicit. "Oh, Avery," she rubbed against me, with my legs spread wide, "oh, I want to fuck your ass. Fuck it so hard." And I was getting drawn in. It turned me on to hear her talk, with such lust, about penetrating me.