"You can sleep with her if you want to, you know," she said.
"What?" I asked my girlfriend Isabella; not sure I heard her right.
"Emily, your ex-girlfriend. You can have sex with her when you go home to visit your mom if you want."
"Uh, wouldn't that upset you?" I was a bit shocked honestly. Isabella and I had been exclusively dating for over 8 months. The sex between us was hot and passionate… in fact this conversation occurred after our second fuck in an hour that night.
"I know you still have feelings for her. I want you to do what you want. I don't want to limit your happiness." I felt a trap being set.
"So, hypothetically if Emily decides to ignore the fact she has a boyfriend and we sleep together, will you then break up with me?"
"No" she said, with no further elaboration
"You don't care?" I actually was almost upset, believe it or not.
"I care. I care about you more than I care about sexual exclusiveness. I have no desire to have another dick in me as long as we're together. Not many men could compete with this thing," she said, lifting my still partially engorged cock. "But men are different than women. You want to spread your seed. Also, your ex girlfriend is not a huge threat to me emotionally. You are not with her for a reason, and it's not because of sex."
I pondered my response. My girlfriend was basically giving me selective permission to cheat on her. Assuming I told her. I still wanted to understand her feelings.
"I'm not saying I want to. But I still want to understand what you're saying. If I have sex with another woman, as long as I tell you, it's OK?"
She paused. "To me Emily is safer than other women. There's a chance I would be upset or disappointed. I have never been exactly in this situation. But, I don't think you having sex with another woman could change how I feel about you."
"Fair enough. I love you" I said, ending the conversation with her, but not the internal one.
"Te Quiero, tambien, guapo" she replied.
A month later I'm meeting Emily for coffee. She looks great. When we were together she was a tad overweight, a bit shy and not the sharpest dresser. She's lost at least 15 pounds, but her breasts still overflow a D-Cup. Instead of being hidden they're half on display in a halter top. She's highlighted her hair and wearing a small amount of tasteful make-up.
"It's good to see you in person," I say. "You look great".
"So do you! You're much buffer than you were 6 months ago. And I like that your hair is a little longer. Also your shirt. And your posture. Why couldn't you be like this when we were together?"
"I was wondering the same thing. You're not as neurotic. Let's face it, you're hotter, and you show it."
"Well, I guess being with some guys besides you gave me some perspective."
We reflect on the past and present as we always do. She's not happy with her boyfriend. She wasn't happy with the last one when she cheated on him with this guy. She's still not easy to please. I'm reminded why she's my friend and not my girlfriend.
I talk about Isabella and our relationship. I hesitate to bring up the sex conversation. Emily knows me too well. She gets a vague version out of me. One that doesn't name her, though does imply that ex-girlfriends are safer.
"Wow." She says. She thinks for a bit. I can read her mind. At first she's thinking Isabella is stupid and doesn't really care about me. Then she wonders if Isabella is right.
"So do you want to?" She finally asks. I wonder if there's a double meaning. There couldn't be… right?
"Uhhh… I guess if the opportunity came up… I mean I love sex, and if it wouldn't hurt her. But it would seem wrong to go after it."
She giggles. "So a woman would have to basically throw herself at you."
"I guess" I say. We change subjects.
My phone rings early the next morning. It's Emily. She broke up with Bryce. It's not the first time, but in the past they've resolved things by the morning. This time he didn't stay the night and they couldn't make up in the morning. "Come over" she says.
She's wearing a white silk robe. Its short, though covers her torso well. She's obviously shaved her legs recently. I know she waxes her pussy. She started doing that after me, when she realized most guys prefer it. Perspective is wonderful.
A few minutes of small talk. Something is up.
"Remember the conversation we had yesterday?" She asks. I nod. I don't have to ask which one.
"Yeah… well…" she says, and drops to her knees and unzips my pants. She yanks down my boxers freeing my hard on and grasps my shaft. She puts the head in her mouth and starts sucking. She's beautiful when she gives head. She's avoiding eye contact.
I just watch her, hands at my sides. She never liked having her head touched when she gave oral. After a few minutes she stops. She rubs her jaw. "Wow, I'd forgotten how thick you are. Bryce is as long, but I didn't have to open my jaw as much for him."
She stands. I embrace her and kiss her, my hard on pressing against her robe. I grab her ass through the silk. It's still firm, perhaps even firmer. She always had a great ass. Too bad she couldn't stand to be fucked there. I feel no panty line.
Emily's ass is small, tight and muscular. Isabella has a "Latina booty" with nicely flaring hips. Both are wonderful yet different.
I pull back enough to untie her robe. She helps shed it. She's got a tiny red g-string on and a red push-up bra that barely contains her tits. They look enormous, especially with her flat stomach.
"A gift from Steve," she explains. "He loved skanky underwear like you. It freaked Bryce out. So I haven't worn this in a while. Hope it was worth it".
My kiss answers that issue. I'm overdressed, but we fix that quickly enough. Soon we're on her couch, me naked on my back, her grinding her pussy against my hard on through her panties, me squeezing her buttocks and kissing her neck.
She pushes the g-string aside and I'm inside her. I slip in easily, she's so fucking wet. Emily hates condoms. I know I'm clean. Emily got tested after she started fucking Bryce. She came back clean and hasn't been with anyone since. And she takes her birth control like clockwork.
I actually think about that as she starts riding me, grinding her clit against my pubic bone. It has been a long time since I've been in a pussy bareback. 45 days… during Isabella's last period we did it in the shower without a condom. But birth control fucks with her system too much to take. So it's always condoms except during the period sometimes.
Emily's coming, and she sets me off too. She's got the strongest pussy I've ever encountered. Emily is a strong woman to begin with, and was naturally born being able to grip a man's penis with her vagina at will. When she comes she involuntarily grips so tightly it's almost impossible not to come with her.
As our heart rates slow the reality sinks in. I kiss her forehead as she puts her head on my chest. My cock is still hard inside her, feeling the heat of our fuck, her pussy juices and my seed. She still has her underwear on.
She slides off me. Come runs down her leg and stains her g-string. She's a sexy mess. She doesn't seem to mind. She used to be far more squeamish. She looks at me, as if to see my reaction. I realize she wants me to set the tone, take the lead. Its odd seeing her almost submissive. "Guess this thong is shot. It served its purpose…" she says weakly.
"Let's shower together" I say.
Showering with her is far more intimate than the couch was. I get to reacquaint myself with Emily's sexy body. Her toned back and legs, her large breasts. The washing starts out functional, but soon I'm behind her, "washing" her tits with one hand, rubbing her waxed smooth pussy with the other, kissing her neck. I love looking at her bald slit. Nothing is hidden. Isabella trims a standard "racing stripe", so I don't get hair in my mouth when I go down on her. But I've always loved a fully bare pussy. It's just so blatantly sexual.