I Take the Plunge!

I sat on the lowest step of the stairs leading up to my apartment, glumly contemplating a row of shoes. Should I wear my black heels or my other black heels to my first threesome?

The first pair of shoes were sling backs, with a lower heel, and spangles sticking to the velvet fabric. The other pair were my workday black heels: round toes, straps, a sort of wing tip cut out design decorating the sides. The whole threesome thing had been Jefferson’s idea, of course. The first pair were party shoes. We were due at Jefferson’s place at 8:00; it was just before 6:00 now. The second pair, with their round toes, seemed to announce my innocence of these matters. They said: I’ve never had a threesome! Look – I’m wearing Mary Janes! I put on the second pair.

Come to think of it, I needed chocolate too, my all-purpose panacea. Of late I’d been sticking to the high quality, 60% plus cacao dark chocolate, the kind that’s supposed to confer health benefits, or at least make the eater feel less guilty about eating chocolate. But not tonight. Tonight I was going straight to the source: Cadbury’s Dairy Milk. I bought two bars, and immediately opened one.

Like I said, it was all Jefferson’s fault. I’d been sitting at my desk on Friday, wondering why I hadn’t heard from Jeremy, when I got an email from Jefferson.

Since you don’t think blowjobs “count” as sex, shall I arrange for you to blow a
boy of my choosing?

I’d been booked for Jefferson’s birthday sextravaganza, and our appointment was for the coming Sunday, but I had thought it would be just the two of us, plus his arsenal of whips and lubricants. Oh, God.

I equivocated. The idea of a threesome frightened me, but then what’s the point of living dangerously if you’re not a little bit frightened? And then I thought, It would blog well. (The siren cry of a blog writer's ego) I thought of my readers (all 12 or so), who would surely appreciate this. And then I thought: Wait, I don’t want my readers to think I’m a slut!

But you are a slut, I reminded myself. And while I fretted it occurred to me that if I did this without being totally enthusiastic, then I was a slut in the bad sense, whereas if I entered into the blowing of strangers with great spirit, I was just living dangerously. Could I get into the right frame of mind?

At last I responded:

I trust you, but I don’t know where your friends’ dicks have been. Like I said, I don’t want to dampen the air of sexual abandon, but I’m not ready to blow a guy with an unknown sexual history. I hope you understand.

Besides, what if he’s ugly?

Unless it was The Boy in the Bathtub (that’s a good title for a book). In which case, yes.

Who is The Boy in the Bathtub? Well may you ask. This is he. I’ve never met him. But a) he’s cute and b) he’s the only one of Jefferson’s friends I have ever seen a photo of. That is, I could confirm that he was cute. The others I only know by reputation. And their reputations are intimidating. Also, I liked Jefferson’s description of the boy.

Anyway, it was time to leave, and I went off to meet Jeremy.

The next day, I met up with Daniel. When we were lying in my bed, I told him about Jefferson’s proposition. “I would do it,” Daniel offered casually. “If you were nervous of doing it with a stranger.”

“Well,” I said, “I don’t know if I’m going to do it or what.” I hadn’t heard back from Jefferson at this point, and generally he’s a pretty speedy emailer (one of the many, many things I appreciate about him). I wondered if he might have been annoyed at the way I was edging away from the whole scenario. Perhaps he’d found someone else willing to take him up on this. Very likely.

But the more I thought about it, the more I came to like the idea of bringing Daniel into the picture. After all, I trusted him, and I knew exactly where his dick had been. And I already knew he was cute. That night, as I still had not heard from Jefferson, I emailed him again, saying that if he was still game, I would do it if I could bring Daniel.

Jefferson called me the following afternoon, in the midst of my nervous IM to Daniel, asking if he’d be willing to join me chez Jefferson. “So you want me to cancel The Boy in the bathtub?” Jefferson asked.

“Oooh.” I sat down on my bed. “You got The Boy in the Bathtub?”

“Lily, this is what I do,” Jefferson said modestly. “I make these things happen.”

The Boy in the Bathtub! “Well…you see… I just…Now I feel bad about the boy in the bathtub!” Had I lost my chance with him forever? Damn my scruples!

“We’ll do that another time,” Jefferson promised. “So, Daniel.”

“Yeah, it’s just, I trust him, and…”

“Bring Daniel.”

“That’s OK?”

“I think it’s kinky,” said Jefferson, “You bringing Daniel.”

“You do?” Was it kinky? How could it be kinky for me to want to feel safe at My First Threesome?

Kinky or not, Daniel and Jefferson and I had agreed, and now it was time for me to prime myself for the kinkiest thing I had ever done, even though it wasn’t the kinkiest thing either of them had done. Not by far. Gloomily, I ate my chocolate.

***

Daniel and I clasped hands as we walked down the hall to Jefferson’s apartment. Daniel, a veteran of one or two threesomes, was perfectly calm. I was not. Also, I suspected that Jefferson would make a move on Daniel, and I wasn’t sure how to bring this up. Would this freak Daniel out? He didn’t have that much experience with guys… maybe he’d be better off in blissful ignorance, until Jefferson attacked.

Jefferson opened the door, and I was pleased to note that he was wearing shorts. Usually he just wears pajama bottoms, which I suppose is his version of Hugh Hefner’s smoking jacket, though not quite as tactile or as sophisticated, I must say. “Happy birthday!” I handed Jefferson his present, and kissed him, and introduced Daniel. They shook hands and eyed one another.

We all seated ourselves on the sofa, with me between the two of them. Oh, God.

“You’re wearing jeans,” Jefferson noted. “Is this the first time I’ve ever seen you in jeans?” He lifted my legs and put them in his lap.

“Maybe,” I said. I don’t wear them often.

“And you’re wearing stockings with jeans...” Jefferson stroked my black nylon toes. “Do you always do that?”

“Oh, the stockings,” I said. “No, they’re part of the outfit.” I paused, to raise suitable interest. “They’re thigh-highs. I figured it was your birthday, I wanted to go all out.”

“Really!”

“Yeah, and I’m wearing a thong too. In honor of the occasion. And a matching bra,” I added proudly. I don’t own many matching undergarments.

“Well, let’s see!” Jefferson sounded positively enthusiastic.

I wriggled out of my jeans, and promptly sat back down on the sofa.

Jefferson tsked. “Come on. Go stand over there,” he pointed, “So we can get a look.”

Gah! Grumbling, I put my heels back on (to give the illusion of slightly longer and leaner legs) and traipsed over to the light, so that Jefferson and Daniel could get the full effect.

“Ah.”

This was embarrassing. I was wearing a thong, after all. I covered my face with my hands and closed my eyes. I wasn’t just on display to Jefferson; it was a full on audience. Jesus!

“We’re not looking at you face,” Jefferson said in his sassiest Southern bitch voice. I rolled my eyes at him and grimaced, but as my eyes were still closed he may not have noticed this.

“Turn around,” Jefferson commanded.

Note to self, I thought, as I obeyed: Lose 15 pounds. My ass doesn’t bother me much, but that’s probably ’cause I don’t often get to see it. Whenever I do, I am reminded that a little exercise couldn’t hurt. And this thong was really small. It really couldn’t flatter my slightly dimpled ass, certainly not when combined with my too-big thighs. At least I had the thigh highs and heels.

“That’s a very small amount of fabric,” Jefferson commented.

When I judged there’d been enough show and tell, I traipsed back to the sofa. “What about the bra?” Daniel piped in.

Oh, what the hell. I took off my top.

“Oh!”

“It’s nice, isn’t it?” I glanced down at the matching pink bra with brown trim. At least my breasts were respectable. I settled back on the couch, while Jefferson disappeared into the kitchen for more alcohol. Daniel settled an arm around me.

Jefferson showed us the birthday cards from his kids, and then somehow we got to talking about comic books; about Gotham City and Metropolis and how Spiderman was actually set in New York City. I looked at Jefferson and thought, He really knows what he’s doing. It was like he knew just what to say to animate and relax Daniel.

“Can we see you with your shirt off?” Jefferson asked Daniel. Daniel obliged.

Then I cajoled Daniel into telling Jefferson the story of his gay and threesome experiences. Which got Jefferson onto teasing me about my lack of experience thereof.

“I don’t know,” I said, “I just don’t think I’d want to go down on a woman.”

“Are you saying you don’t think you’d like the taste?” asked Jefferson.

“...Yes.” Was this anti-feminist?

“So you think your own taste is bad?” he said, making a not illogical leap.

“Yes.”

“What do you think you taste like?”

“I don’t know!…”

Meanwhile Daniel had slid his fingers inside my underwear. Jefferson leaned closer. “I like this,” he said, reaching out to touch the pink fabric. “What do you call that?”

“I think that’s ruching.” (It was a kind of gathered fold).

“Very nice.” My bra came off, and he bent to suck my right nipple. Daniel sucked my left. I giggled.

After a moment or two Jefferson announced, “Lily, would you mind leaving me alone with Daniel for a minute?”

“What, really?”

“Yes, really.”

I glanced at Daniel; he nodded. “OK.” I stood up.

“Go into the bedroom,” Jefferson added.

This was the beginning of Act II, right? The action. “OK, OK.” I padded down the hall in my stockings and thong.

In Jefferson’s bedroom, as usual, I studied the bookshelves. At last they both came in. “Lily,” said Jefferson, “I want to make out with Daniel for a while. Is that OK with you?”

Now, even though I had suspected Jefferson would be all over Daniel, for some reason that hadn’t been on my mind when I traipsed down the hall. Aha! I glanced at Daniel. “Is that OK with you?”

Daniel indicated that it was, indeed, quite OK.

“Let me get my specs,” I said. I had taken off my glasses and put them on one of Jefferson’s nightstands. I wanted to see this properly.

I settled into the armchair next to the bed. Daniel got onto the bed and Jefferson slid on top of him. They kissed.

I leaned forward to see Daniel’s face. His eyes were closed, and his mouth strained towards Jefferson’s when Jefferson teased him by pulling away. Jefferson ran a hand over Daniel’s groin. I moved forward a bit more. I was literally on the edge of my seat.

Jefferson helped Daniel out of his pants and soon had his mouth wrapped around Daniel’s cock. Oooh. Then they switched, and I watched Daniel bury his face between Jefferson’s legs.

“Now come here,” Jefferson said to me. They lay next to one another, looking smug. I grinned and bent my head over Daniel’s cock, then Jefferson’s; just briefly, but the situation seemed to require that kind of acknowledgement.

“Daniel, you suck my cock, and Lily, you sit on my face,” Jefferson directed. This time, I watched close up as once again Daniel obediently bent over Jefferson’s cock and began working him over. After a particularly long suck, he boasted, “I don’t have much of a gag reflex.” I settled on top of Jefferson’s face and as he licked me I watched Daniel’s head bob up and down. Finally I motioned to Daniel so I could get him in my mouth, a sort of three-way suck off. The sensation was overwhelming. Not like Oh my God this is the hottest thing ever, but overwhelming in the sense of a real sensory overload: cock in my mouth and tongue and boy smell everywhere, it was like my skin and senses were being bombarded. But otherwise I must say I felt pretty comfortable, all things considered.

Here’s what I really wanted, and I don’t know why I just didn’t demand it. I wanted to be on all fours, with Jefferson fucking me from behind while I sucked Daniel off. Or possibly riding Jefferson (which I’ve never done. Once I asked, ‘Can I ride you?’ purely as a courtesy and he said, ‘No,’! Who says No?! I guess it was the dominant thing...) while he sucked my nipples and I sucked Daniel. Anyway, I’ve been fantasizing about the former position ever since I read a short story in which it happens. But I didn’t say it; maybe I was waiting for Jefferson to tell me to do it. Which was dumb.

“Lily, I want to see you fuck Daniel,” said Jefferson at last. I smiled, because I always like to fuck Daniel. Daniel settled back on the pillows and I climbed over him, and licked and sucked him for a bit. He was nervous; after all, we usually don’t have sex in front of an audience. I smiled and stroked him and was so glad I didn’t have to be the one worrying about my erection. Jefferson sat in the chair, which began to take on a new significance for me: that armchair was dirty: a voyeur’s chair!

After a minute or so Daniel was ready, and I slid on top of him. “Daniel,” I said, “Daniel.” I rocked back and forth, and I wasn’t at all embarrassed. “Jesus, Daniel,” I went on, as my legs started to shake. “Look at me. I get on top of you and already I’m practically coming.” We kissed, and I let my hair fall around my face to cover him. I felt very protective of him now.

I came pretty quickly. Daniel didn’t at all, but after a nice effort, he tugged off the condom and collapsed.

“That was really sweet and sexy and hot,” Jefferson said. I smiled at them both, because “sweet” is not usually a word to describe having sex in front of someone, but at the same time I felt very tenderly towards Daniel, who is, of course, Sweetheart Daniel.

Then Jefferson came and flopped on top of me; I started to giggle. I was sandwiched between two naked men, and, again, this was a sensation that was totally unfamiliar; my skin was covered from all sides. Jefferson laughed, and then Daniel did, too.

Then Jefferson tugged me to the edge of the bed and assumed the position I’m beginning to think of as the Jefferson Special, tugging my legs up around his neck and fucking me while he stands. As he fucked me I heard “Oh!”s and groans coming out of my mouth. I watched Jefferson’s face, and I was dimly aware of Daniel, sitting quietly in the chair.

“Your turn,” Jefferson rasped, and moved aside so that Daniel could assume the same position, with the exact same girl: me.

Oh, this I liked. It wasn’t the physical sensation so much as the knowledge that I was being fucked in turn by each of them. I liked it; I liked being this fuck object that two men could casually share.

Then Jefferson took over again and as he fucked me I caught a glimpse of my legs, sticking straight up around Jefferson’s body. My legs didn’t look half bad from this angle, I realized. My thighs looked more proportionate, anyway.

Suddenly Jefferson slapped my ass, hard. “No!” I cried, because it hurt. He didn’t hit me again, but kept on pumping his cock into me with a steady rhythm.

At last he pulled out with a sigh. I think Jefferson’s only come once with me. I really feel like I’ve failed if I can’t coax an orgasm out of a man; I love seeing that release of tension, that blissful collapse of sinew and muscle. I’d really like to make Jefferson come more often.

It was late now, after midnight. “I’d better go,” said Daniel. He had to go all the way back home, and get up early. Jefferson offered to have him stay, but Daniel declined.

I followed Daniel to the door. “Are you OK?” I asked. I had expected to be the scared one, but now I was worrying about him.

“Yeah,” Daniel smiled. He looked so cute and good. “I’m glad I could do that for you.”

“I wouldn’t have done it without you.” He looked embarrassed but pleased. Didn’t he know how much I trusted him?

When Daniel left Jefferson asked if I was hungry. “I can’t believe I’ve never cooked for you,” he said.

“I am hungry, but if I eat now, I’m going to be tired.”

“That’s OK.” Jefferson started retrieving food from the fridge.

“I mean, I’m going to fall asleep,” I clarified.

“That’s OK,” Jefferson repeated. “We can fuck in the morning.”

***

In the morning I went to work as part of Jefferson’s campaign for 44 blow jobs. I sucked him for so long, my lips were numb. Really! But no dice: “You’re in it for the long haul,” Jefferson informed me.

Oh, God. (Wo)manfully I went back to my task, back and forth over his dick, sucking and licking. I gagged on his dick, and swallowed saliva, and licked and sucked some more.

At long last Jefferson jerked and groaned. Had he come? He hadn't ejaculated.

“You came?” I hadn’t known that Jefferson could come like this.

“Oh, I came,” he assured me. “It’s not that common for me, this way, but I came.”

I was sort of afraid he had faked it because he was getting bored with my cock sucking. Truth be told, my mouth was exhausted. I smiled at him: "You're my favorite pervert," I cooed.

Finally we clambered into our clothes and headed for the restaurant I had tried to go to with Jeremy. To my great delight, we were seated right away. Jefferson and I grinned at one another over our coffees and biscuits and sugar cured bacon (Oh God, it’s so delicious, like bacon ice cream; I don’t even like bacon and I swoon over this stuff….). He could name all the songs that came on, which I appreciated.

When we left I said, hesitantly, “You know, I don’t fight you about everything you ask me to do on principle.” I meant all the hedging about the threesome, my adaptation of the invite and my telling him “No!” when he’d hit me last night. “I’m not saying no as a tease.”

“I know,” Jefferson said.

“It’s not that I object to fucking your friends,” I went on, “It’s just that this is new for me and I have to negotiate my comfort level.” I meant: I had to maintain some autonomy, or at least the illusion of autonomy with Jefferson, even if what I really wanted was to be told what to do; that is, not have any autonomy. “I don’t mean to jerk you around and hedge so much, but I want to go slow.”

“I know.” Jefferson said again, and smiled at me. I smiled back. And we walked together to the train station in the cold, talking about nothing.