V for Virgin!

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Every girl should have their best guy friend take her virginity. At least, that's what I think. Yes, I'm that girl. That weird girl that always asks for the impossible and just happens to be secretly in love with her oblivious--rightfully so--best friend. Woe isn't my name though. It's Cassie. And with my impromptu agreement to be a surrogate mother due to financial instability, I'm in a bind. Losing my virginity to a baby is not my cherry-picking dream. I have maybe a month to get him to agree before the in vitro process starts. Of course, he and his boyfriend know absolutely none of this. [M/F/M]

Romance / Erotica
G.S. Glow
4.6 41 reviews
Age Rating:

Two boobs, a hole, and a wanted pole

A bigger dilemma of my life happened when my gay best friend unintentionally turned me on at some random pool party. Up until that point, I’d never had the urge to do a guy or a girl for that matter. At twenty, I could honestly admit that I’d never been attracted to anyone that wasn’t a movie star. I was a late bloomer to some, yet the idea of a relationship with a movie star would never happen. In that choice, I had safety from STD’s, unwanted babies, and heartbreak when I selected which screen hottie would cause my delightful vibrated orgasm.

The rabbit was an all-time favorite.

“So, Ethan, I was wondering...” I started as if it were a normal conversation with anyone of my friends.

If I wasn’t so comfortable around him I wouldn’t be able to ask this rather uncomfortable question. Especially since I had no way of knowing how it would change our relationship in the future. Unfortunately, I was that comfortable with him.

His pine-green eyes and charcoal eyelashes fluttered as he shifted his gaze away from his book to glance at me with a raised eyebrow. “Do you plan on finishing that question?”

I shifted, suddenly wary. My light blue cotton shorts slipped higher up my thighs, and I grabbed the back of my black tee, pulling the excess material behind me as an afterthought. The general effect was the material stretching across my breasts with the idea of that presenting me as a sex kitten in waiting.

That might have worked for a straight guy.

What the hell are you thinking, Cassie?

That was the thing though, I wasn’t thinking, not really. To keep up with that ideal I let the words spill out. “I want you to take my virginity.”

It hadn’t come out a gobbled mess. Each word had been clear. I was either going to yip with joy like a new puppy or... Oh shit!

Those seven words bounced off the walls of his apartment, taunting me, teasing me with my stupidity. Saying it in my mind was a different reality to saying it out loud, and Ethan’s silence made me wonder if I’d already ruined what we had.

What was I doing? How could I just say it like that?

I knew deep down our friendship was stronger than that, but my insecurities were ugly beasts. Blurting the words out had not been the best choice. I glance down at my chest and quickly released my shirt. My face flushed with humiliation. I’d even tried to make myself physically appealing to him. Two boobs and a hole between my legs kept insisting it wasn’t possible to be appealing to him.

What was I thinking?

Resisting the urge to bow my burning face into my hands, I let my mortification consume me as I watched him, waiting for him to point and laugh, to tell me to get out for being so ridiculous, but all he did was blink at his paperback copy of Neverwhere, a frown creasing the sides of his full, slightly chapped, peach-colored lips. The only sign that he’d heard me was the subtle movement of his half-day stubble shadowed jaw clenching and releasing.

His tongue swiped his bottom lip before he turned his head towards me. The book in his hand flexed in his tightening grip and new tears in the binding formed.

“Cassie,” he paused, his eyes lifting to the ceiling like he was searching for help on what to say. “You were there when I told you I was gay, weren’t you? I mean it was five years ago, but it did happen.”

It was settled. It was as simple as that for him; the end of the story. While I felt stupid for blurting out my secret desire to have sex with him, I knew this was a small hiccup to expect. That didn’t stop the speed of my heart. I placed a hand over my chest and felt the pounding beneath my breast.

“Of course I was there. I know you’re gay,” I managed, relieved he hadn’t laughed.

I knew this wasn’t going to be easy. I’d thought about this for a long time, long enough to include Ethan’s boyfriend—Seth—a part of the ‘devirginize Cassie’ mission. It had to be Ethan and if Seth came as a result then I was okay with it. Seth was like a rippling supermodel.

A piece of my curly brown hair fell onto my warming cheeks as I sighed and folded my arms across my chest. I turned my upper body towards him and leaned closer, settling inches away from his side and reiterated the truth I knew, “I know you like guys. I understand that, but I don’t trust anyone else to do it. You’re my best friend, Ethan. And let’s be honest, at the rate I’m going I won’t lose it until I’m like,” I paused, my eyes rolling upwards as I pretended to do some mental math, “eighty.”

He rolled his eyes and turned the rest of his body towards me, lifting his leg and settling his bum on his calf. “Don’t be overdramatic. You’re just picky.”

It was my turn to be exasperated. “It’s more than that and you know it!”

He chose not to comment on that, but he gave me a knowing look and bowed his head. “Why now? You’ve never cared before.”

Now that I had no plans of telling him. My two main reasons were for me and me alone, at least for now.

Sharing my reasons would be way too embarrassing. The first reason: his glistening abs and a pair of black swim trunks at a pool party. My tweaked nether regions had gone into a frenzy that night and ever since, so much that wet-dreaming became ritual for me. When I realized that I truly did want him, Rational Bug came and bit my ass. ‘Cassie Sandwich Fetish’ haunted my sleep and wake time and it didn’t take long for Seth to start appearing in my erotic dreams after that. Being hyper-sexually aware of Ethan meant the same for his significant other.

Ethan was always walking around shirtless and Seth was touchy – as in he was always touching me or Ethan. Seth’s enjoyment of physical contact was borderline molestation. Maybe that was too strong of a word, but the truth is it had never bothered me before because I’d never noticed it. Now that I did notice it hot showers were a thing of the past and when those ice-cold ones didn’t do the job... well, let’s just say that my bank account has dwindled. Sex toys, good ones at least, are not cheap and I’d burned out three within two months.

Seth, for a gay guy, really knew how to touch me too. He would run his fingers up my bare thighs when I had shorts on or bump me from behind with his hip. He would pat my ass and make comments about my small chest... he even took a finger and pulled the neckline of my shirt down to peek inside. I wasn’t a nympho, at least I didn’t think so, but my sex-drive remained in warp speed and now I had to do something about it.

And then there was the second reason, one that was still a little too surreal for me to even admit. That was not the way I was going to lose my virginity, but that was also the reason Ethan and Seth needed to know about the most because I was counting their support.

“Well? Why now?” Ethan repeated his question.

I wasn’t going to let the answer ‘because you and your boyfriend make me horny, Ethan’ slip out, but it settled on the tip of my tongue. It was the easiest answer, after all, plus it wasn’t a lie.

Biting my lip, I shrugged. “I don’t know. I guess I want to know what it feels like. I’m tired of waiting and masturbation can only do so much.”

A horrified expression crossed his face, but he shook his head quickly, his sandy blonde hair falling into his eyes. His book dropped to the floor with a thud and he rubbed the back of his neck. “Are you in love with me? Is that it?”

I slapped a hand to my chest and let my mouth drop, faking an outraged expression. I vehemently shook my head in denial. “Ethan, I’m twenty, not twelve. I just want you to stick your pole into my—”

He held a hand up; literally face-palming me, and the feel of his smooth hand brushing against my lips sent chills over my body. “Shit! Do not finish that sentence!”

I scoffed and shook his hand off reluctantly. My teeth sunk into my bottom lip when his hand, instead not touching me at all, fell to my knee. “Hey, I happen to be very sexy. Brett Carson told me that my lips are great for sucking—”

“I’ll kill you,” he said, his eyes darkening before his expression shifted from menacing to thoughtful. He raised an eyebrow and cleared his throat. “I didn’t know Brett liked you.”

I shrugged and scooted forward, forcing Ethan’s hand to slip up to my thigh. My breath caught in my throat as he allowed his hand to shift with the movement. “I didn’t either,” I said, hoping he didn’t hear the high pitch change in my voice. “And don’t change the subject! I know it’s me, once again, asking a lot of you, but I love you. I feel safe with you and I know you won’t hurt me or be a jerk after it’s done. Or worse, leave me.”

His expression changed again. It was his businessman one, his emotionally cold, yet slightly piqued with interest one. Making the person it was directed at thinks they might have a chance, but not to fuck with him.

Hope kindled inside of me because I knew at that moment he was taking me seriously.

“How can you be so sure?” he asked.

“That you won’t be a douche afterward, well I’ve known you since you were like twelve and you love me too much.”

Ethan scowled and shifted further down the couch, away from me. “I love you, but I’m not deflowering you. That should go to someone you’re in love with.”

I clucked my tongue against the rough of my mouth making a ‘tsking’ noise. “Why not? We can watch gay porn to get you hard. I don’t object to porn. Porn is my life!”

He flinched and patted my thigh. “I didn’t need to know that.”

“You know everything else about me,” I mumbled, trying to keep my pout at bay. “All I want you to do is—”

He nodded with a scoff. “Is stick my pole in your—”

I held my hand up. “Okay, you’re right that wasn’t the best word choice.”

“Ya think?”

I sighed, rolling my eyes and sweeping a hand through my hair for dramatic effect. “It’s not that big a deal, Ethan.”

“Oh, isn’t it? In that case, let Brett do it!” Ethan lifted his hand from my thigh and crudely cradled my jaw, using his pointer finger and thumb to squeeze my lips into a forced pout. “These lips were made for sucking cock.”

Surprised at his vulgar admission, my eyes widened. Ethan didn’t do vulgar or even gentle dirty for that matter, at least not with me. I waited for him to release me, but his darkening gaze remained on my lips and for a moment I could swear I saw him leaning into me.

It had to be my imagination. It had to be. So I jerked my face away and faked a gag. “His hands are like meat hooks and his face looks like a very ugly bulldog.”

His hand didn’t resurface on my thigh, but it did rest between our knees. “Well, it’s not a big deal, right?”

“Ethan!” I reached over and punched him as hard as I could, but he barely flinched.

“For argument’s sake, let’s say I consider this, what about Seth? Does he get a say in this? He is my boyfriend, after all.”

“Well technically, since you like guys and I’m a girl, it wouldn’t be cheating.”

He scoffed. “That is the most retarded thing I’ve ever heard! You do realize that Seth’s asinine fear of losing me is to you turning me straight, right?”

I frowned, stretching my legs and reaching behind me to scratch my back. “Is that even possible? Besides, he only has that fear because he’s your first real boyfriend.”

Ethan snorted and settled his elbows on his knees, his chin in his hands. “No, it’s not possible. He may be my first boyfriend, but not my first lover. I’ve told him that.”

I smiled. “You’re such a freakin’ ho.”

He grunted.

“So, if it’s not possible, then what’s the problem? It’s just sex!”

“If it was ‘just sex’ you wouldn’t be asking me.” I thought I’d lost him, but he turned his face and stared intently at me, his dark brows drawn together in serious contemplation.

“Are you sure you want it to be me?” Ethan asked.

My mouth dropped open. Was that it? Was this all it would take? I expected a lot more leg work on my part. To not seem too needy, I pretended to think about it before slowly nodding.

“You understand for me to take your virginity I have to be-um-well...” His face burned a lobster red as he stumbled over the words.

“Turned on?”

He inhaled sharply and then nodded.

“Yes. That’s why I was thinking that maybe we could ask Seth to join us, or you know, there’s always the porn I mentioned earlier. I’m adventurous but double penetration my first time might be a little much,” I said, feeling relieved to have finally gotten the idea of Seth joining us out.

Was I dirty for wanting them both? Was it wrong?

The idea of the three of us alone and together just felt right in every way every time I thought about it. I only hope Ethan didn’t think less of me for wanting that.

Ethan blinked and his lips parted. It was then I noticed the steady flush spreading across his cheeks and down to his neck. Maybe this idea was a little more intriguing to him too.

“How did I know you would say that? And you think I’m the freakin’ ho?” he asked playfully.

I pouted and folded my arms across my chest. “A virgin can’t be a ho.” Blowing on my nails with an ‘I-know-something-you-don't-know’ look, I nodded. “Seth tells me things, Mr. Sub. I could be your new dom too if you want. I think I could handle a whip pretty well and how hot would I look in slutty leather?”

“Oh lord,” Ethan mumbled. “Why do I put up with you?”

The corner of my mouth lifted in a smile. “Because you love me and I’m your snuggle bunny.”

I bit my lip to contain my excitement. I could see it in his eyes. He’d given in. My brain grew legs and leaped with joy as he scrubbed his hands through his hair.

“Oh man,” he mumbled. “I can’t wait to hear what Seth has to say about this.”

“He’ll want to know why he can’t pop my cherry.”

Ethan groaned, his shoulders sagging, his face now hidden in his palms, “That’s exactly what he’ll say.”

I patted his muscular shoulder, letting my fingers linger longer over his warm skin. “We probably won’t even have to talk him into it.”

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