Ask Eva Amore Vol. 01

Author's Note: I thought I'd try a different sort of story, using fictitious letters, and a fictitious sex advice columnist. The letters are obviously much longer than would ever be used in a column of this nature, but I felt the added length was needed to tell the stories. All characters involved are over the age of eighteen.

Ms. Eva Amore has been offering her many readers and fans the naughtiest most scintillating sex advice in her syndicated "Ask Eva Amore" column for over a decade. Formerly a professor of human sexuality at a prestigious university, Ms. Amore uses her extensive knowledge and experience regarding sex to craft poignant, yet humorous responses to her audiences' inquiries. All questions, comments, and stories may be directed to askevamore69@sexpress.com.

Dear Eva Adore,

My fiance "Melanie" is bisexual, and before meeting me, she was convinced that she would end up with a woman. She'd been fucked over by a lot of men in her past, and had basically lost faith in the gender before meeting me.

We have a great, very active sex life, and until recently Melanie had never mentioned missing the company of a woman in bed. However, she'd been hanging out with her friend "Kimmy" who's bisexual, and involved in the kink community, and hearing of Kimmy's escapades made her simultaneously aroused and jealous.

In particular Melanie missed being with multiple partners, so she proposed the idea of having a threesome. She'd had multiple threesomes before we'd begun dating, but I was a three-way virgin. And while I'd of course fantasized about it, when actually presented with the idea it sounded more scary than arousing. However, it also struck me as something I shouldn't pass up, so I agreed to one if the circumstances were right.

Melanie took this as an open invitation, and no more than a month after discussing the idea of having a threesome, asked me if I was still serious about it. She explained that there was a woman in her yoga class named "Brandy" she'd been flirting with, and would be interested in joining us. Unbeknownst to me, Melanie had even shown Brandy pictures of me, including one of me standing in the shower with a full-on erection.

Before I could get too angry about this invasion of my privacy, Melanie informed me that her friend thought I had "a great body, and a really nice dick". She then asked if I'd like to see a picture of Brandy, and pulled up a picture on her phone that made me instantly hard. On the screen was a photo of a thick, pale brunette, wearing nothing but stockings, performing fellatio on a large, black dildo. The picture was taken in a full length mirror, and showed Brandy on all fours servicing the dido in a doggystyle position. "That could be your dick," Melanie said coyly.

Two days later Brandy came over to our house, not so coincidentally gifting us a bottle of brandy. The chemistry between the three of us was palpable right off the bat, and after a few drinks we made our way to the bedroom.

Brandy had been dressed fairly conservatively, so when she disrobed I was surprised to see her in an extremely sexy, open mesh bodysuit get-up that left nothing to the imagination. Melanie never wore fancy lingerie like that, but she looked pretty hot herself topless in nothing but a skimpy, white thong.

I was a little dumbstruck, and not really sure where to begin, so Melanie took charge by playfully pushing me onto the bed, and ordering me to take my shirt off. The girls then took their place on either side of me, and Melanie kissed me while Brandy ran her hands over my chest, even sucking my nipple a little bit.

Then Melanie started fidgeting with the zipper of my jeans, and taking the hint, Brandy helped slide off both my jeans and briefs. "Wow, you're a lucky woman," she remarked to Melanie upon seeing my large endowment.

Melanie continued kissing me, while also starting to stroke my penis. We were still learning each other's boundaries, and Brandy asked if it was okay if she played with my balls, and Melanie made it very clear she could do anything she liked to me.

So not only did Brandy squeeze and tickle my balls, but she gave them little butterfly kisses, and sucked them sweetly. Getting aroused by the sights and sounds of another woman orally pleasuring me, Melanie soon joined.

Teasing me for as long as I could handle, the ladies french kissed each other right in front of my penis, occasionally showering it with little kisses and licks, letting their tongues swirl around the head with the delicacy of a figure skater twirling on virgin ice. Then Brandy finally took the entire length of my penis in her mouth, while Melanie sucked my balls.

They continued to perform oral sex on me for what felt like an eternity, while I nearly passed out from ecstasy. Believe me dear readers, a double blowjob feels even better than it looks, and nothing can make a man feel more powerful.

The rest of the night was a dream. Both girls sucked me generously whenever I so much as put my penis anywhere near their mouths, as well as bringing each other to orgasm with their oral skills. I even got to taste Brandy, licking her out from behind with her big ass in my face, while she was going down on my fiance. I did this until her juices were dripping all over my mouth, and then finally mounted her from behind.

Melanie is a petite girl, so the opportunity to be with a thick, curvy girl like Brandy was a dream come true. Watching her ass ripple as I pounded it brought me too much pleasure so I had to pull out after less than a minute of making love to her to keep from cumming.

It wasn't until a little later in the night, after having made love to both girls, that I came inside of Brandy while Melanie was riding my face. The girls then sixty-nined, bringing each other to a final orgasm while I watched.

Due to the late hour and alcohol in our systems, we invited Brandy to spend the night. I slept between both lovely ladies in our California king bed, and had no trouble falling asleep.

Then at some point in the night I woke up, with my erect penis pressed firmly against Brandy's large, bare ass. Heat was radiating off it, seemingly sending me an invitation. I started running my free hand over her ass, and down her crack, taking a second to tickle her pussy. Then in her semi-catatonic state, Brandy reached behind and started fondling my penis, playfully but lovingly. I returned the favor by rubbing her clit, feeling her wetness drip down my fingers.

I pressed my penis against her pussy, hoping she'd let me inside her, but she wanted to lubricate me first. Quietly sliding under the sheets, she wrapped her lips around my penis, and treated me to maybe a minute of passionate, gentle sucking.

Then with both of us nice and wet, I slid inside her. In the moment my mind was overcome with arousal and sleepiness, so I failed to consider that this wasn't within the parameters Melanie and I had set before engaging in a threesome. We'd both made it very clear that we wanted each other to be involved every step of the way.

After a few pumps, when it did dawn on me exactly what I was doing, I started moaning a little, hoping it might wake Melanie up. But Brandy put her hand over my mouth, and Melanie sleeps like a log anyway, so she didn't wake up.

The whole encounter didn't last long, five minutes tops, before we simultaneously orgasmed, her body convulsing on my cock, as I came inside her uncontrollably. She then slipped away to the bathroom, while I fell right back asleep, and that was that. Neither of us mentioned it the next morning, and Brandy left bright and early.

Melanie and I are usually very honest with each other, but I still haven't mentioned this encounter. I genuinely have no idea how she'd react, and am not sure it's worth the risk of telling her. She can be the jealous type. Any advice would be greatly appreciated. Is it best to just keep this little secret, or should I open up? If I do tell my fiance what happened, how do you suggest I go about it?

- To Tell or Not to Tell

Dear To Tell or Not to Tell,

Okay, so first you should know that many guys that write me have real problems. Things like not being able to get laid, being insecure about their penis, or not being able to satisfy their woman.

So let's start by putting this in perspective. You have a bisexual fiance that thinks you should be having more threesomes, you have a big dick, you recently had two women playing with your big dick, and you got a hot piece of new ass after presumably thinking you'd only be getting some from the same woman for the rest of your life.

Now the bad news. Relationships, including open relationships, are built on trust. It sounds like the two of you set boundaries before your threesome, which is a great first step, but it sounds like these boundaries may have been unclear. If your fiance thinks you knowingly violated these boundaries, that doesn't bode well for her trusting you in the future, let alone letting any more hot yoga babes go down on you.

Not once did you mention how your fiance felt about the threesome. It sounds like she got off a few times, so that's great, but overall did she enjoy the experience? Did it make her at all jealous? Did it make her miss having a woman as a sexual partner? Are threesomes something she'd like to continue exploring? Before doing anything else you should get the answers to these questions, if you haven't done so already.

Check the vibe from there. If she's expressing a lot of regrets about the threesome, figure out why, and drop the topic for the time being. If she enjoyed it as much as you seemingly did, ask what she enjoyed most. If she doesn't bring it up, mention how much you enjoyed watching her with another woman, especially when they sixty-nined with you as a spectator. Then tell her how much it turned you on to see the way she looked at you, and held you as your dick was being caressed by another woman's lips. Chances are if she enjoyed the threesome, she enjoyed seeing you getting pleasured by another woman.

After it's been established that you both enjoyed the experience, tell her what happened while she was asleep. There's no need to lie, but there's also no need to be detailed. Tell her that while you were half-asleep, Brandy started pleasuring you. Tell your finance you were hoping she'd wake up organically, but you came before this could happen. She may not take this well, but then again, maybe it will turn her on. Either way, use the discussion to clarify or re-calibrate your sexual parameters. If she's upset, perhaps you offer her the chance to spend a night with Brandy, or another woman to make it even. Give her the option of letting you watch or not.

However, the thing that concerns me most about your letter isn't your lack of being forthright; I'm more concerned that in your description of the threesome, you hardly mention feeling aroused by anything your fiance did. I understand that it's exciting to get a new piece of ass, but don't let it affect your desire to get married. Your fiance and you can have a life of fulfilling sexual experiences so long as you're honest with each other, and communicate clearly.

- Eva Amore

Dear Eva Amore,

I'm originally from a small town, and wasn't exposed to much debauchery until attending college. Now in my second year, I'm enjoying the freedom of living off-campus, and the amount of house partying that entails. Recently I attended a pool party thrown by some friends that live just a few blocks away. Mind you, I grew up in a small, landlocked town, so the sight of bikini babes has been a rare occurrence in my life.

Naturally, I was awed and aroused by all the fit, tanned ladies flaunting their perfect bodies in cheeky bikinis that covered very little, but I was mostly able to keep my arousal in check. That is until a girl named "Grace" showed up.

A tall, slender Asian girl with long black hair, and smooth brown skin, I was instantly awe-struck by Grace's presence. She showed up in a bright red bikini top, and a transparent sarong that barely hid a scandalously small, matching bottoms. But it wasn't until she took the sarong off that I realized she was wearing a full on g-string.

There were other girls at the party wearing small bottoms, and cheeky bikinis, but nothing nearly as revealing or naughty as Grace's red g-string. Much to my surprise, none of the other girls in attendance gave her any dirty looks, not even the ones that were there with their boyfriends. In fact, numerous girls asked her where she got her bikini, and complimented her for having a tremendous body, and the confidence to show it off.

I, for one, could not keep my eyes off her. I found my eyes repeatedly drifting to her derriere, and I kept trying to position myself so that I'd be behind her. There were definitely a few other perverts I noticed really checking her out, and I even saw one guy that thought he was being discreet, secretly snap a few pictures of her bare ass.

However, most of the guys acted like it was nothing out of the ordinary for a drop dead gorgeous, Asian vixen to be prancing around a party with a tiny piece of floss down her ass crack. Some guys seemed to ignore her entirely, and others casually approached her and struck up conversation, as though everything were entirely normal.

For her part, Grace exhibited no shyness about being more or less naked. She'd freely dance to songs she liked, letting her ass shake wild and free, and would occasionally apply tanning oil, smearing it over her bare ass in plain view of everyone. During a few of these episodes I struggled to hide my arousal under my swim trunks.

The whole time I was at the party, I was dying to talk to her, to just bask in her presence really, but couldn't work up the courage. Even the beer didn't help. Then finally our paths crossed at a beer-stocked cooler. As I approached the cooler, she slipped right in front of me, and bent over to fish a cold one from the bottom. Her ass was just inches from my crotch, and I could see the lips of her pussy, which her g-string failed to completely cover.

Then turning around, more or less catching me with an erection, staring at her ass, she said, "Shit, I can't find anything but Keystone Light. Do you know where they're hiding the good beer?"

I demurely told her that I wasn't sure, quickly grabbed a Keystone, and bustled on out of there.

This was a few weeks ago, and I've been kicking myself ever since for not having the courage to even talk to her, when she had the courage to flaunt her beautiful ass in front of a hundred horny college kids. I'm not sure if an opportunity like this will come knocking again, but if it does, what's the best way to approach someone in a revealing bikini without coming across as a total pervert?

- Fear I Missed Out

Dear Fear I Missed Out,

Yikes, where to begin here. First off, you are a pervert. Embrace it, there's nothing wrong with that. Second, you refer to this situation as an opportunity, as if a woman wearing a thong is an invitation for you to fuck her. I'm guessing you haven't gotten laid much, if ever, so maybe it's time you reconsider the way you think about women.

A woman might choose to wear a skimpy bikini in public for a variety of reasons. Maybe she works out, has a killer body, and wants to show it off. Maybe she has total confidence in herself, and doesn't give a fuck what anyone else thinks of her bikini. Maybe it turns her on, and she doesn't need the attention of horndog guys to get sexual affirmation. Maybe she wants to work on her tan. You get the point.

But yes, there is a certain kind of woman that wears micro bikinis in public places because she enjoys teasing others, knowing she's driving men, and maybe even a few women wild. How do I know this? Because I'm this kind of woman.

I rarely wear anything other than thong bikinis to a beach or pool, and I love the attention, good or bad, this attracts. What I don't like though are the sneaky perverts. Don't be that guy that's secretly trying to take pictures on your phone, or touching yourself under your towel. You're not fooling anyone. On more than one occasion, I've approached men that were trying to secretly take pictures of me in my thongs, and on more than one occasion the men I've approached have taken off running. Don't be that guy.

I've also had plenty of encounters where men have approached me. Sometimes it's to offer a compliment and move on, others it's to ask where they can get a bikini like mine for their wife, and yes, sometimes I've been clumsily, or creepily hit on.

If I like the vibe I'm getting, I'll allow men that approach me to take pictures. Once after a particularly steamy shoot, I rewarded my newfound photographer with a nice blowjob, but that's not something you should expect, obviously.

Look, this isn't rocket science. If you see a woman you're interested in, it can't hurt to approach her. In this particular instance, there's nothing wrong with addressing the elephant in the room; if she wore a g-string to a pool party, she's probably cognizant of the fact that people are focusing on that. You could say something as simple as, "You look nice in that bikini."

That's not creepy, and it lets her know that you're interested. But if nothing else, at least this experience has given you some material for the spank bank. I'm thinking you'll probably need it.

- Eva Amore

Dear Eva Amore-

For the past three months I have been in a wonderful relationship. My partner "Jenna" is highly educated, funny, easy-going, fun to be with, and beautiful. Our sex life is mostly good, but it's lacking in one area that is crucial to me.

My last partner "Brittany" was not great. She was controlling, shared no common interests with me, and would shut down for weeks at a time when in a bad mood. However, she was a curvaceous, sensual blonde, that satisfied me sexually in a way no other woman has.

Namely, she explored parts of me that I never even knew I wanted explored. I'll never forget the first time it happened. For my birthday she offered to satisfy any sexual fantasy I had, and my request was for her to pretend she was a masseuse at a rub and tug joint. She got really into it, even having me wait outside while she got into costume.

When she was ready, and I knocked on the door, she answered in a tiny kimono that covered less than half of her voluptuous ass. She even had the chopsticks in her hair, the whole nine yards (Cultural appropriation, yada, yada).

She then had me pour sake for the two of us (the man's always supposed to pour with sake), and "negotiated" the kind of massage I'd be having while we drank. We settled on something she branded the "complete package", which in her words meant she'd been massaging my "entire package".

She began by leading me to our shower, bringing the bottle of sake with her. She scrubbed down my entire body, casually stroking my cock now and then, but doing it in an absent-minded way to make it seem like she was simply cleaning me, not trying to jack me off.

Then near the end of the shower, she grabbed the bottle of sake. She stood behind me with her large breasts resting on my back, cupped my balls from behind, and brought the sake to my lips. "Drink," she said. "It will loosen you up."

She poured the sake down my throat, then stroked my cock a little. "Very good, now have one more swig. I want you nice and loose."

Having heard her use the term twice, I asked her what she meant by "loose" and she said, "I meant for this," and she pressed her two fingers against my prostate, before moving them slowly up to my anus. "I want to massage you in this way," she said, sliding her middle finger inside of me.

I had never had this done to me before, nor had I tried it on myself out of curiosity. In my surprise I sort of jumped, but Brittany just laughed. "Relax, I just want to pleasure you," she said.