Virgin Gigolo Ch. 09

Robin pulled back and swung a leg up and over his, straddling him and guiding his cock inside her. She was moving slowly, just like she'd started the first time, but it didn't last for long. "What do you say, shall we try a different position?" she asked. "This is called cowgirl, and if I turn around, it's called reverse cowgirl. Do you want to try that?" I saw his head nod, and moments later Robin had swung herself around and guided him into her pussy. Reaching for his good arm she pulled it around her hip and guided his hand in place. "I like this position because you can stroke my clit," she told him. I could see his fingers fumbling without doing much good, but she told him just the opposite.

"That was nice," she said a while later, after turning around once again. "Here, keep playing with my clit," she said, guiding his hand between her legs once more. "That always feels so good." Raising his hand to her mouth she sucked his finger before guiding his hand back between her legs. "Wet and slippery is always good," she told him.

She began a rundown on different positions, telling him how, if he could stand, she'd get on her hands and knees on the bed and let him take her from behind. She told him how if he could sit up, she'd sit on his lap with his cock inside her. She told him how nice it would be to lie on her side and let him take her from behind. She told him how fun it would be if he could stand to do it on the kitchen table, all while gradually fucking him harder and faster. His head rolled back and forth until, with a groan, he again came inside Robin.

I was used to two-hour time slots, Tiffany wasn't. I didn't even think about it, that she'd been taking care of Ricky virtually the whole time that we'd been there, until suddenly the phone buzzed. Looking down I saw "On our way back -- coast clear?" Robin had heard the phone ding, and looked at me. I motioned to the phone and nodded in confirmation.

"Ricky," she said, "I'm sorry to go but our time is up, and your parents are on their way home. Maybe we can do this again sometime? Would you like that?" His answer was unintelligible to me, but I knew it was positive.

I motioned to the envelope of money in the hallway, and Robin just looked at it. She looked at me and smiled, and then just walked by it. When we got in the car, I texted that Ricky was happy and in bed, and that we'd wait outside until they got home."

"You didn't use a condom," I said as we were sitting there waiting.

'Yeah, I know." She didn't offer any explanation for a few moments. "He was a virgin and he'll never experience sex again. I just thought it was better to give him the real thing."

"And you did it for free."

"Would you have done any different?" I looked over at her as we pulled away from the curb and shook my head no, but I couldn't get the whole evening out of my mind. She had given a young man, who had never experienced sex, and never would again, a precious gift. She'd taken care of him in a way that a lover would, with no questions asked.

Three weeks later Melissa called and asked Robin if she'd given Rick her real name. When she asked why, Melissa said she'd gotten a call from Sandy. Rick had died, but over the last three weeks he'd dictated a list of names that he wanted to invite to his funeral celebration of life. Included on that list was Robin and Brent, and although Sandy didn't know who "Robin" was, she remembered me as being Brent.

It truly was a celebration of life, including pre-written dictated Thank You notes from Ricky to many people that had been special to him. Teachers, friends, doctors and nurses, relatives, his sister, and Robin. For everyone else, there were specific things that were mentioned, but for Robin -- it was just her name. I saw Sandy glance at us with tears in her eyes when her name was read, and she mouthed a "Thank You."

"Robin," I said as we were in the car afterward. There had been some food available, but we didn't know anyone else so hadn't stuck around for more than a couple of minutes.

"Yeah?"

"You're a special woman. I'm not sure why this seems to be the time, but what you did for that man, that boy... I can't... I don't... I mean, I do..." I stumbled, unable to say the words.

"Danny, stop it!" she interrupted, "Just say whatever you're trying to say."

Suddenly it was easy. "I don't care that you've been married before. I don't care that you were the hot chick in school that I thought wouldn't give me the time of day. I don't care that you have the same job as I do and don't come home until the early morning hours several nights a week. I want you to be my wife. I want you to marry me." She said nothing for a few moments.

"Are you asking or telling?"

"Does it matter?"

"Absolutely. My husband, Dennis, told me we were getting married. If you're telling me, the answer is no. But if you're asking me to marry you, ... well, I'll have to think about it."

"Hmm." I said, "well, I guess I'm telling you that I want to marry you, but I'm asking you to marry me."

"OK, I'll think about it."

It wasn't a yes, and it wasn't a no. Even though we hadn't talked about getting married, I knew it was something I wanted.

~

"Somethings bothering you," Robin said when we were cuddled in bed. Robin had spent the night before with a client, so I hadn't seen her until earlier today when she came home.

I sighed, bothered -- but yet not. "I sucked a cock yesterday."

"Oh? Lindsey and Paul?" I was surprised Robin remembered their names, but Robin didn't seem at all surprised that I confessed I'd sucked Paul's dick.

"Yeah."

"Want to tell me? I always figured they wanted you to do that."

"We did it once, and she had Paul suck me hard so I could fuck her again. I did, and after I came a second time, she wanted Paul to do her too. She had climbed into his lap facing out while riding him, and she told me to lick her clit at the same time. So I did." I pictured in my mind what had happened. "She was bouncing on him pretty good; I was trying to follow her clit with my tongue when she just rose up a bit more. His cock popped free of her pussy as she slid down behind it -- and it went in my mouth. I'm pretty sure she did it on purpose; as soon as he went in my mouth her hand went onto the back of my head to hold me there."

"Probably. She's been trying to talk you into sucking him forever, hasn't she?" I nodded. "Did he cum in your mouth?"

I nodded again. "I'm not into men, but I can understand how you like sucking cock."

"Why is that?"

"I, uh... I have to admit, it wasn't as bad as I thought it would be. I could tell it felt good to him, too. His cockhead... it was just the right size, and I swear, running my tongue around it, I could feel how he was enjoying it. And it kept growing and getting bigger and then... it erupted I don't know how else to explain it; his cock swelled up and then exploded into my mouth."

"Did you swallow?"

"No. Lindsey was saying, "Don't you swallow! Don't you swallow! Give that to me!" Oh my God, it almost gagged me, but I kept it in my mouth, and when he quit spurting, I closed my mouth and moved up to Lindsey. She wanted me to kiss her, but I didn't, I just pushed his cum out of my mouth and into hers."

Robin nodded, saying nothing for a moment. "Would you do it again?"

"Not if I can help it."

~

It was almost a month later. We were lying in bed after making love, about to go to sleep, when Robin said "Why?" I wasn't sure what she was referring to until I asked. "Why do you want to marry me?" she clarified.

I thought about it for a bit before answering, telling her how she'd always been my dream girl, how when she'd been the head cheerleader and getting her picture taken with Adam I'd been so jealous, wishing it was me. I told her how hearing her mother telling mine that she'd walked in on the two of them fucking, that I'd so wished it were me. I told her how, even when she seemingly dissed me at her wedding, that I had wished that it was me. When she'd gotten married, I'd had no self-confidence. I'd never been able to tell her I was interested, to ask her on a date, to see if maybe I was mistaken, and she might have responded to me in a positive manner. Now, I had newly earned self-confidence, I was no longer a virgin, and although we both had unusual professions, I knew I didn't want to be without her again.

"And," I added a few moments later, "because I love you. I've loved you since we were kids." She didn't say anything, absolutely no verbal response before I fell asleep, just her hand slowly stroking my arm.

~

"I don't understand," she said the following morning, when we were still lying in bed.

"What?"

"I've been married, and it didn't work out. To say nothing about me being a whore, for God's sake. Sure, we call it escorting, but I've got an appointment this evening where I'm going to be paid to put on an evening dress with no panties. We're going to a meeting where he's going to show me off as his sexy girlfriend, and then we're going to his hotel room where he'll fuck me. I'll sleep in his bed, pretend he's the world's greatest lover, and then I'll fuck him again tomorrow morning. And then I'll come back here in the morning with more money than I'd make in a week in the business world."

"What's the difference between that and me being in Mary's bed, or numerous other women's beds, having sex with them for money? I'm just as much of a whore as you are."

She didn't answer immediately. "Gigolo," she said.

"What?"

"Gigolo. A male prostitute is a gigolo." She giggled.

"I don't care what it's called," I answered, rolling to her, my hand coming up to caress her arm, "I only have sex with my customers. I make love with you." She didn't say anything, and after a couple of minutes of nothing I rolled over and padded into the toilet to take a pee.

Coming back, I opened the drawer to get clothes out when she called me. "Danny?"

"Yeah?"

"OK."

"OK? OK what?"

"OK, I'll marry you."

That was the start. There were a lot of things to iron out. As the old saying goes, once bitten, twice shy -- and she had been bitten. Eventually we included a lawyer and a prenuptial agreement that defined what each of us was bringing, including substantial economic assets, and how if this didn't work out, anything that was brought into the marriage also went out of the marriage with the original owners. We discussed future income, expenses, investments, and at the suggestion of the lawyer (who we had to confess to what exactly it was that we both did for income), a clause that took marital infidelity out of any reason for a divorce.

Unlike when she married Dennis, we almost didn't tell anyone about it. We finally called my parents, and Robin's, and told them we were planning on getting married before a judge as we didn't want a big to-do about it, but they were having nothing to do with that. I had no idea before, but found out my mom had always hoped that maybe Robin and I would get together and had always been disappointed that in our youthful days we really hadn't seemed to mesh at all. I wondered, when she confessed this, if she had any idea that her son and future daughter-in-law were both professional sex workers. Somehow, I doubted that.

I think it was really my mother that was pushing for a wedding where 'she' could invite guests. Robin's mother outwardly went along with those wishes, even though she'd had that party when Robin was married the first time, and eventually they agreed that we would all compromise with just a smaller ceremony. Mom got her wish to invite her closer family and we all got to invite a few friends. And of course, the "small" gathering kept gathering steam, and people, until we cut them off and told them we weren't going to have a "big party." They didn't like that, but agreed.

Robin and I were already living together; for us, this wedding would just legally and publicly be saying we were committed to each other, so we didn't see it as a big thing. Robin and I both had a couple of friends that we invited, and together we invited Savannah and Melissa since we worked with them. The only close friend that my mother invited was Mary Wilson. I hadn't really realized until I saw her name on the list that my mother considered Mary Wilson to be that good of a friend, but questioned immediately when her name went on the list. When I asked, my mother said that with her own mother being thousands of miles away, Mary had been her substitute "mom," her confidante, and friend, for years. I couldn't help but wonder what my mother would have thought if she knew that her confidante and friend had been paying her son for sex for quite some time or that she had seduced her son and taken his virginity. I strongly doubted that she knew that Melissa had introduced Mary to lesbian sex and she was seeing Melissa almost as much as me, although I'm sure that would have had less impact than knowing I regularly graced her bed. Although I knew that Mary had never said anything to mom about me, I wondered if they really were that good of friends, had she possibly ever confided with my mother that she was regularly having a gigolo visit?

And, of course, there was also my mother's good friend, Martha, who was also my wife-to-be's mother, Martha. Although she never slipped and let out to anyone else that she was my customer, that I was her Lothario, several times I saw a lusty look in her eye that almost always resulted in receiving an appointment request from her the next day -- and sometimes even the same day. We didn't get together with either of our parents all that often -- but it soon became obvious (at least to me) that whenever we spent any time at all with Robin's family, with Martha, I almost immediately got a call for an appointment with her. There was no doubt in my mind that Martha liked to be fucked by her daughter's fiancé. I knew she liked sex, but I'm sure that the illicit aspect of being fucked by her daughter's boyfriend had a lot to do with it as she quite often would ask if I'd yet fucked her daughter that day, or perhaps if I'd go home that evening and fuck her daughter.

The actual ceremony was anticlimactic, and just like that -- we were Mr. and Mrs. We had a honeymoon in the Caribbean before returning. I asked Robin, while we were on our honeymoon, if she'd noticed her mother had been making almost regular appointments with me after we'd seen her, and she hadn't. When I asked her what she thought about that she was pretty pragmatic about it -- "does she pay her bill?" I assured her I collected up front, and she just shrugged her shoulders.

I told Robin how her mother, ever since we'd been engaged, commonly asked about whether I'd been with her that morning, or whether I would that night. "She really seems to get off on knowing that you and I are lovers."

"Hmm." She didn't say anything for a moment. "I never knew my mother had so many kinks. I guess we all do, don't we?"

"Does it bother you? Should I cut her off?"

She didn't answer immediately, and then shrugged her shoulders and replied with a pragmatic, "It's work, right? As long as she pays her bill."

Martha tried several times to contact me when we got back, but I put her off. I made excuses several times, and didn't see her for almost two months after the wedding. She was practically insatiable when I did. Unlike other times, she wasn't so much interested in me doing her ass as just fucking. I started with her from behind, on her hands and knees doggy -- but she guided me to her pussy instead of her ass. I was on the verge of coming the first time when she pushed me away and rolled over to finish with me missionary, face to face. A while later, after I'd recovered, she climbed on and I did her cowgirl. Still not sated she climbed off, leaving my condom covered cock behind, and straddled my face. I sucked and tongued her to her third orgasm after which she finally rolled off and onto the bed beside me.

"Oh my God. I can't believe I just made love with my daughter's husband."

"You didn't," I answered instantly. "You just had sex with your paid sex toy. The only woman that I make love to is your daughter."

~

{Ed. Note: The following may seem familiar as it intertwines with CWB 6 -- Bachelorette Party. Tiffany and Brent have previously been briefly introduced to Stacy, Ellen, Josette and Carrie in CWB 6 -- Bachelorette Party: https://literotica.com/s/cwb-6-bachelorette-party}. You may wish to revisit that story as this tells that encounter from Robin and Danny's perspective.

~

"Hey Brent," Mellissa started when I answered the phone, perhaps 6 months later. "Do you remember Ellen?"

"Your friend that we saw where I almost ran into my mother and she saved my ass?" She laughed.

'Yeah, that's the one. How would you like to pay her back for helping you out?"

"What have you got in mind?"

"Her brother is getting married. She and a couple of girlfriends are having a bachelorette party in Palm Springs. She wanted to know if maybe you and Tiff could perform your phony arrest routine, and maybe the standing 69, for the girls? She said she heard so much about it at Kathy's party she always felt left out that she didn't get to see it. I told her I thought you'd agree to do it for cheap since she helped save your ass." She laughed.

We wouldn't have normally taken a gig like that, traveling several hours, but I checked with Robin, told her what happened before, and we said we would.

"Which one of you is Stacy?" I asked as we pushed the door open even wider and forced our way in. Ellen, dressed in just bra and panties, I recognized when she opened the door. Even if I hadn't recognized her, a wink at us confirmed she was expecting us.

"Police!" Robin ordered. "Stay where you are!"

"We've got a warrant for Stacy," I spoke with authority, holding the phony paper up for all to see. "Which of you is Stacy?" Ellen pointed her out, although the look of surprise on Stacy's face, and not on the others, gave her away.

"Hands behind your back," Robin ordered as I grabbed one arm and she grabbed the other.

"Am I under arrest?" Stacy gasped, the shock in her voice saying she really couldn't believe this was happening.

"Frisk her," Robin said, "make sure she doesn't have anything concealed."

I ran my hands over her body, from head to toes. Sliding up her legs one at a time, under her dress, finding her ass bare with just a thong panty; letting the fingers of one hand slide across her crotch from one side and then my other hand doing the same when I slid up her other leg. Standing, I moved behind her, sliding my hands around to her breasts, stopping when I felt her nipples protruding through her dress. "I think she's smuggling bullets," I said to Robin and the room, keeping a stern look on my face.

"Better do a strip search!" Robin replied. Sliding my hands to her shoulders, I slipped the dress straps to the side and down her arms, folding the dress off her chest to expose her breasts. Pulling the Velcro catch on my own shirt, I slipped it off and dropped it to the floor before reaching around her with two hands to again fondle her now naked tits.

"I'm not finding anything unnatural," I said to the room, rolling Stacy's nipples between my fingers. "Whatever it is, she's got it well hidden. I'm thinking we may have to do a complete strip search and body cavity inspection." Unclasping one of the handcuffs, I slipped the dress from her arms and down, reclosing the handcuff before pushing the dress completely down to puddle at her feet -- leaving Stacy clad only in her panty.

"Take that off!" I heard Robin say, only to glance up and see her attention directed at a thin woman with practically no tits at all -- but obviously erect nipples protruding through a body conforming dress.