Virgin Gigolo

"Tell me about Mary," Melissa said when I sat down in the chair. She'd called and asked me to come by so we could talk about some upcoming gigs.

"Mary called?" She nodded. "What did you tell her? Or, perhaps I should ask, did she say what she wanted?"

"She said she'd talked to you about wanting Savanna or me to join her for a threesome. Is that what she said?"

The question seemed strange. I thought it was exactly what she'd said, but something in the way that Melissa asked it made me wonder. "Yeah, pretty much. She asked about Melissa after I told her about the Black-Tie affair and how Savanna kissed the bare-breasted woman and shared a mouthful of my cum. She said she'd always talked about a threesome with her husband, but they never had."

"She specifically asked to have a threesome with you?" she semi-repeated. Again, I had to wonder thinking back on Mary's exact wording. What was I missing?

"Yeah, she said she and her husband had discussed having threesomes before and she'd always wondered what it would be like to do a woman and asked if maybe Savanna would consider joining us. I told her you like women too, and asked if it had to be Savanna, and then I gave her your number."

"Did she specifically say she wanted a threesome? Or did you assume that when she said she'd always wanted to try it with a woman?"

Like the dunce that I was, it suddenly clicked. Melisa had just asked me three times about whether Mary had asked for a

threesome

as if that were wrong. Everything that Mary had said ran through my head, specifically when she'd asked about whether Savanna or Melissa would consider playing, she'd stuttered just slightly before saying "join us" and I realized that she'd been afraid to say "join ME." Perhaps she'd been more specific with Melissa, or perhaps Melissa was more in tune with her customers, but she recognized that Mary wasn't so much interested in a threesome with me as a twosome with a woman. "Ah...." I said, letting Melissa know I suddenly understood.

"We had a good conversation. She is so sweet; she was afraid she'd hurt your feelings to admit she

just

wanted a woman to herself. She did say she'd always wanted to share her husband with someone else, but she said she had no desire to pay two of us."

"I told her none of us work for free, but I'd do her for free if we did that as I know she doesn't have a lot of money and she's already been spending a lot of money on me." Melissa laughed.

"What?"

"I don't run into many

virgins

, especially ones in their 60s, but I never charge a virgin for the first time either. I told her we could get together and if she ever wanted a repeat, we could discuss payment the next time." I just nodded. "She's really nervous about it."

"Really?" I was surprised, with Mary's sister having been a "kept woman" for years, and Melissa being an escort, asking someone for sex would almost seem

normal

for her. "She's nervous? She sure didn't have any problem teaching me a thing or two."

"Yeah, but she'd been having sex with men for what, almost 50 years?"

I ran the calculations in my head. "Yeah. Probably forty-five?"

"So, is she a forty-five-year inexperienced virgin with women or a forty-five-year experienced lover with men?"

"Hmm. Yeah, I guess. So, you're going to see her?"

"I am. She was really nervous, and I suggested we meet for dinner on Wednesday night, get to know each other a bit, and then we could go back to her house."

"Wow, a date?"

"Yeah, that's how escorting usually works; you meet, spend the evening together, and then usually go to a home or hotel."

"Oh yeah, I hadn't thought of it that way."

~

"Brent," Melissa started when I answered the phone perhaps a month later, "I've got a fortieth birthday party. Need a man and a woman, you interested?"

"What's the gig?"

"Strippers, phony police, pretending to arrest the birthday girl. She's currently single and her friends want her to get fucked. Typical get naked, let them fondle and play with you, and you'll need to seduce the birthday girl and make her a happy camper. I've got Tiffany lined up as your policewoman partner. One fuck for you of the birthday girl included, if anyone else wants to do you or Tiffany, it's extra. If the birthday girl doesn't want to fuck, you do Tiffany while everyone watches."

"Who's Tiffany? I haven't met her yet."

"Oh, yeah. Cute gal, 22, a couple of years older than you. Goes to the same Uni you are. We should probably do like with Savanna, get you together and let you run through the spiel together. Are you in?"

Twenty-two.

When she said that it dawned on me that my earning money for college had been going on for over a year and a half as I would be twenty in about a month. When she said that Tiffany was a coed, my mind immediately started running through all the cute gals I'd seen at the U who I'd seen and had a "Wow, I'd love to fuck

that

" thought about. I had to shake my head at myself; I'd been fucking MILF's seemingly forever, but when it came to gals my own age, gals I might be interested in, I still had zero self-confidence. After years of being a dweeb, a library nerd, and being tongue-tied around women my age, it was hard to break my internal thoughts of being unworthy -- no matter how many pussies were regularly riding my cock. But there were hundreds of cute gals on campus, I just couldn't help but wonder if I'd ever crossed paths with her before.

"Brent?" she broke my reverie.

"Yeah, I'm in."

"Oh perfect! We need to get you over to Marty's for your police outfits, what's Wednesday look like for you?"

~

"Right on time," Marty said when she opened the door, "Tiffany just got here. Come on in," she said as she turned to lead me down the hall to the fitting room. I stepped in and my eyes got big as I froze.

"Robin?" Her face looked shocked; her mouth fell open.

"Danny?"

Marty looked back and forth at the two of us. "I take it you two know each other but haven't met as Tiffany and Brent?" I glanced at her and nodded. She shrugged her shoulders, scrunched her face in an 'oh well' gesture, and said, "Well, get to know each other, I'll be right back," and stepped out.

I was in shock.

Robin, my life-long fantasy dream girl, the unattainable cheerleader who was so totally out of my league; the daughter of the woman who was having me fuck her in the ass once a month or so, was now Tiffany? A stripper? An escort? She'd been married, and except when I'd seen her at the lingerie party, I hadn't seen her since her wedding more than two years before. "You're Tiffany."

She nodded. "That's my working name. You're Brent?" I nodded.

"I never expected to see someone I grew up with."

"Yeah."

Marty came back right at that moment with two blue "police" uniforms. "Here, try these on." Mine looked like what I expected, but the deep vee of the one for... "Tiffany" (I had to correct my thoughts from "Robin" lest I make a mistake sometime in the future and call her by her real name) was much too sexy for a non-sexual police uniform.

I'd long since gotten used to being naked around unknown women, but Robin wasn't an unknown. Something about getting undressed in front of my dream girl made this different. Regardless, I turned my back towards her and pulled my shirt and pants off. "Underwear too," Marty said, "You'll want to go commando. Too hard to pull underwear off while everything else is velcroed in place." Knowing that Robin's eyes

had

to be on my backside, I bashfully stepped out of my underwear and slipped the pants on. If it had just been Marty, like the last time, I would have just stripped off and been naked without a problem.

"OK," Marty said, reaching down and taking a measurement on the leg, "we'll need to lengthen that a bit. Try the shirt." The shirt was just a bit tight across my shoulders, so she told me to take that off also, and she'd widen it just a bit. I began to take the uniform back off when I heard her say to Robin, "The pants fit good. Take the shirt off, I need to narrow it a bit." Glancing over my shoulder, Marty was playing with the vee on Robin's shirt, the lace of her white bra visible. "Have you got a cup-less or a half-cup bra? You need it in black, that white one will show." I saw Robin shake her head no. "Ok, so... 32B? Or C? I've got one back here that should work, if not we'll have to get you a new one." Take that one off when I come back, and we'll try the shirt without a bra so I can see how it fits."

Stepping completely out of the uniform, I reached over and put my regular pants back on before turning around. Marty took Robin's shirt, collected my pants and shirt, and said she'd be back in a few minutes. Looking over at Robin, she was now standing there in her uniform pants and a white lacy bra.

"This was a bit awkward, wasn't it?" Robin asked, making no effort to put her shirt back on.

"Just a bit." I felt like I had to say something so asked, "Are you still married?"

She shook her head no. "No. I haven't seen you since the wedding, have I?"

"Just once," I said, "although I don't think you recognized me that time."

"When was that?" She asked, a touch of curiosity in her voice.

"Melissa's lingerie party. At Helens. All I was wearing was a mask."

"Oh My God. That was you?" I saw her eyes drop to my crotch. I was glad I'd put my pants back on.

I nodded. "That was me." I paused letting her remember. "You had a black eye. Is that why you're not married?"

"Some," her head nodded, and I could see her evaluating how much she wanted to say. "That was the final straw."

"Sorry." She shrugged her shoulders.

"Shit happens." I nodded. "What about you? Married?"

"Oh hell no." I laughed. "Believe it or not, I've never even had a girlfriend."

"

What

? I remember Helen saying you were the best lay that she'd had in years."

"I didn't say I wasn't fucking, I said I've never had a girlfriend."

"Ok, here you go," Marty said coming back into the room just then, carrying two bras. "Take that bra off and try this one. It's just a quarter cup but your breasts are so firm I'm sure it will work." Robin took the bra and hesitated. I sensed a bit of reluctance and realized it was because of me. "Oh, come on, girl," Marty said, also picking up on the slight reluctance, "You're going to fuck with this guy and you're acting bashful?"

Whether she realized it or not, I was also feeling a bit bashful. I'd had sex with hands full of MILF's by this point. I'd also had sex with Melissa and Savanna, both of whom were young and quite sexy, but it had

only

been sex, and I'd had no other interaction with them. Robin, on the other hand, I had known for easily ten, probably fifteen years and had filled many a Kleenex with a load, dreaming of doing exactly what we were going to do tomorrow -- something that I never really expected would happen,

with her

.

I looked away. I was pretending that

this was nothing

, getting undressed and dressed with a beautiful woman that I'd long had a crush on present, having a beautiful woman getting dressed and undressed in front of me, but the growing cock in my pants said it was something else.

"That was fast," I instead commented to Marty about her quick return.

"Just the bras," she answered, "I've got the alterations being made, they'll be done shortly. Ok, that's not it, is it?" She said to Robin, and turning I found Marty with a hand on Robin's tit, feeling the fit. "This is too loose. You're a little small for a C cup. Here, try this one, I think it will be better." The bra she had tried on didn't quite cover Robin's areolas, her nipples perked above the material, but supported to the outside quite well, pushing in and making her look quite busty. Marty reached up behind Robin and unhooked the bra, and Robin shrugged it off, momentarily standing topless. She didn't look over at me, but I knew she knew that I was watching. "No, this one is a front clasp," Marty corrected Robin as she started to align it wrong, "arms first." I watched as she pulled it in place, snapping the hook on the first try, although it did

nothing

to cover her breasts. It lifted and supported, leaving her nipples and areolas

almost

completely bare. "Oh, that's perfect. Quite hot. OK, I'll be right back with the shirt." With that she turned and walked out again, leaving me with a near erection in my pants and my fantasy girl virtually topless.

"This is... um..." I started to say, but not knowing how to finish.

"A bit embarrassing?" Robin finally added again.

"Yeah. I've known you like... forever."

"Me too. I've fucked a lot of strangers, funny how someone you know can make you..." she didn't finish.

"Yeah," I nodded, wondering as I did whether her nipples were hard from arousal or whether they were normally erect. It certainly wasn't cold in the room, although it wasn't blast furnace hot either.

"Ok, here you go, try these on," Marty said, bustling into the room again. She tossed me the uniform pants and shirt, walking up and handing the shirt to Robin.

"That was fast," I said, having expected it was going to take quite some time to modify the pants and shirt.

"It's quick and easy when you've got everything set up already and somebody who knows what they're doing. Put them on and leave them on." I pulled the shirt on, then dropped my pants and slipped into the uniform pants. Turning back, I found that Robin had already finished pulling the Velcro-closed shirt in place. Whereas before I could see she had her white bra on, now the bra was hidden, with just the two protruding buttons of her nipples visible through the shirt breast.

"Good," Marty said, turning back and looking at me, and then turned back as Robin finished tucking in the shirt. She again reached for the vee of the shirt, shifting it back and forth a bit. "Yeah, much better. You want your boobs to show a bit as you move." She turned back to a box that she'd brought in originally and set on the table. Reaching in she pulled out belts, badges, and shoes. "It's the accessories that sell it," she said, handing me shoes and doing the same for Robin. "I had your shoe sizes from last time. You'll need to wear these, they look like real uniform shoes, but just like the clothes they use Velcro so you can easily get them off."

Both of us sat to put the shoes on, and when I stood back up, she handed me a belt that looked just like an accessory belt that policemen wore. "You can carry your condoms in that little pouch," she said, indicating the small, heavy leather, pouch on the side. "Ok, so sleeves," she said, reaching up and gripping the bottom of my sleeve. "Grip it tight and pull slightly sideways, not just down." She pulled, just as she'd said, and the sleeve ripped away surprisingly easily. "Button front," she said, "grab it top and pull down and out, or the bottom and pull up and out. If you grab the middle and pull away from the body, it will fight a little bit. It

will

come free, but up or down works better. Either way, once it's free, it will pull out of the pants pretty easily too." With that, she reached in, grabbed a handful of my shirt right by my belt, and pulled up. "I like up, if you pull down you almost have to reverse the pull to get the bottom to clear the belt easily." Just as she said, the shirt pulled up and out. I shrugged it free.

"Belts. Velcro partition on the sides. Grab the front and pull forward or pull backward, but give it a firm jerk. It holds really well if you pull firmly, but a quick jerk almost always breaks it in two. If one side comes free but not the other, just jerk the other side too." She reached in, grabbed the belt buckle, and jerked -- the entire front of the belt coming free and pulling out. "You always need to pull the belt first; it will fight the pants coming free otherwise. Pants are the same as the shirt, Velcro down the legs both inside and out, but usually if you grip the sides, jerk down, the outside will pull free and then the entire pant can just be dropped." With a quick jerk on each side of my pants, the Velcro ripped free. Grabbing the back of the pants she just pulled, and everything slipped between my legs -- leaving me naked except for my shoes. "Usually you'll want to shed the shoes first, it looks kinda funny with the heavy shoes and nothing else. The Velcro pulls free really easy if you catch a heel with one toe and just lift. If not, you'll have to lift your foot and use your hand to help." She looked at me standing there naked, and Robin, fully clothed. "Hers works the same. Want to try? Any questions?" I shook my head no.

"Looks pretty straightforward," Robin answered.

~

"Heya, Robin..." I said as the elevator door opened into the parking garage.

"Call me Tiffany or you'll make the mistake when you don't mean to."

"Yeah. Sorry. Hey, Tiffany... would um...would you like to go get a coffee or a drink somewhere before we go see Melissa? Maybe get caught up a little more?"

She stopped and turned to face me, her eyes searching my face. "Are you asking me out?"

"I uhm... I wasn't particularly thinking of it

that

way," I clarified, "I was just thinking... we need to catch up." She nodded.

"Ok. I'll call Melissa and tell her we'll be there in...what, hour and a half? Coffee?" I nodded. "Ok, I know a place. Follow me."

~

"What happened?" I asked when we'd found a somewhat secluded table. Being late afternoon, the Starbucks wasn't quite as crowded as it would have been in the morning.

"My marriage?" She asked, confirming what I was prying about.

"Yeah, you seemed so happy at the wedding."

"I thought I was. But it turned out

he

wasn't the man I thought he was. I'd seen some... traits... when we were dating, but always thought that was because we were single, and we'd change when we were married. But I thought I loved him, thought if we both gave of ourselves to the other..." She paused for quite some time before continuing. "It's just that he never gave anything." I sat and nodded, didn't even need to do anything except to throw out a few confirming questions as she talked. "I knew he used to never make the bed when we were dating, but I'd make it for him, and he'd always thank me. After we got married, making the bed was suddenly "my job." When I washed clothes, I'd put his in too, but after we married, it was "my job." I figured to complete my school and have a degree; he wanted me to stay at home to make dinner and give him blow jobs and have sex with him at night." She took a sip of her drink.

"I thought it was an OK arrangement at first, but it just kept getting worse. Giving him a blowjob in the evenings became him bragging about how good I was at blowjobs to his friends, even while I was there. There was one evening when he'd had more than a couple of drinks, and his three buddies were there, and he called me in and told me to show his friends how good of a cock sucker I was. I refused, and he grabbed my arm, and in a really ugly voice said, 'Bitch, when I tell my wife to give me a blow job, I don't want backtalk.' He forced me down onto my knees and opened his pants, pulled it out, and made me blow him."

"Oh my God, Robin..."

"I was pissed, I'd never been so angry with him. He was holding my head down on his cock, and telling his friends about how good I am, and he said, 'What do you think guys, you want to have a go with her when I'm done?' I was practically numb from what was happening, but when he said that, I bit him."

"His cock?" I asked, cringing at the thought of teeth penetrating my most sensitive organ.

"Drew blood."

"Oh my god, what happened?"

"Obviously, he flipped out, pushed me back, and then he hit me. Face, chest, boobs, hit me in the gut and then punched me in the face. That's what gave me the black eye. 'You fucking bitch!' he said, 'You'll pay for that. If I tell you to suck a cock, you

will

suck my dick or regret it. You're my wife now, and you do what I say.' He turned to his friends and said, 'Larry, you first. Pull out your dick, my wife says she wants to suck it.' Larry tried to say it was OK, he didn't need that, but he insisted. I ended up sucking all three of them off, and then they left."