My first client was not going to be easy, that was for sure. But I was up for the challenge. My twin sister, Julie, and I, started our firm with the promise of delivering wonderful first time sexual experiences to women (and men). I wasn't going to let Shelley's anxiety ruin her introduction into lesbian sex. Our "My First Time" agency had been my dream for quite a while.
Over the years, our sexual adventures led us into some interesting experiences. The ones I liked the most were when we got to introduce someone to sex the way they wanted it. We fucked a number of virgins. It was so fulfilling to watch someone grow into a new area of their sexuality, that we decided to turn it into a business.
Julie is a tennis instructor, and doesn't have a ton of time on her hands, so she took the business development side. I had been laid off from my job and had plenty of time, and plenty of energy. So I took the client fulfillment side of things. I became an escort.
Julie and I decided that we'd do this escort business our way. We only take referrals, meaning - no website, and no public location. Julie has a special email account where we communicate with potential clients. We vet them well and have them answer our proprietary set of five questions to learn how best to serve their needs.
Shelley came to us from a friend of a friend. She'd been married for twenty years, had just become an empty-nester, and gotten divorced. She told Julie that, deep down, she'd always wanted to try having sex with a woman. But her anxiety about it, and a bad marriage, kept her from fulfilling the dream - until now.
I was to meet Shelley at a small restaurant in a town away from where she lived. I knew the owner, and he always kept a very private booth available for me and my "friends". If all went well, we'd move to our house - one we kept only for business.
I arrived a bit early and ordered a glass of Pinot Noir to sip on. I'll admit, I was a bit nervous. This was the first time I was going to have sex with someone who was paying me, and quite well.
"Donna?"
The voice drew me out of my thoughts.
"You must be Shelley," I said, extending a hand to the woman who approached the table.
The woman standing in front of me was drop-dead gorgeous. Her long blonde hair fell most of the way down her back and over her shoulders. She was tall, with large firm breasts, a flat stomach, long legs and slender arms. I was not expecting a forty year old woman to be this beautiful. I wondered in that moment why she was anxious about sex at all! She looked very put together in a knee-length sleeveless white dress (with a bit of cleavage) and heels. More business woman than mom.
"May I sit?" Shelley asked.
"Of course!" I said quickly. "Pardon my rudeness."
Shelley sat down. She held her back straight, as if manners and posture were important. I made a note of that. Of course, it only served to show off her incredible boobs. I tried not to stare, but I detected nipples protruding from her bra. Good sign. I also realized that my mid-thigh red dress was both shorter and more revealing than hers. I noted that for the future.
"Wine?" I asked.
"Please!" Shelley said. "A chardonnay please," she said to the server who had magically appeared. Okay, so I'd arranged it that way, but Shelley didn't know that. It's amazing what you can learn from searching people's social media.
The server reached to the side and brought out an expensive chardonnay and a glass. She had her drink in seconds.
"Oh my!" Shelley said.
"Only the best for my clients!" I said with a smile.
Shelley took a big sip. Clearly she was nervous.
"I've never done anything like this before," Shelley said after taking a second gulp.
"It's okay, Shelley," I said. "To be honest, neither have I."
"Say what?" Shelley said, her eyebrows raised a bit.
"I'm actually a bit nervous myself," I admitted. "You're my very first client."
"Oh my!" Shelley said. "You know, that actually makes me feel better."
I could see her shoulders relax. My confession had had its intended effect.
"Can I just say that you are incredibly beautiful?" I said, honestly.
Shelley blushed.
"No one's called me that in a long time," she said.
I reached my hand across the table and put it on hers. "Shelley. You are one of the most gorgeous women I've ever seen. Most women would love to be intimate with you, me included."
"Wow!" she said. "I, well, I just didn't know."
Clearly she'd been repressed for quite some time. I loathed the man who did this to her.
We exchanged small talk. I learned about her history and her family. Some of it I already knew from Julies' vetting process, but it was good to hear it from Shelley's lips. Those lips, by the way. I wanted to kiss them so badly. Not yet.
"So, this is really your first time too?" Shelley asked after getting a second glass of wine.
"It is," I said. "My sister Julie and I just started this business. You came highly recommended from Ellie Jameson, who's a friend of yours, yes?"
"Ellie's a dear," Shelley said. "She told me to trust you totally. That'd you help me overcome my fears."
"My sister and I have known Ellie for a long time," I said. "What she says is true. I'm only here to help you fulfill your desires."
"Speaking of which," Shelley said. "How do we get started?"
I chuckled. "Well, we've already started. We're getting to know each other. It's a prelude to the rest of the evening."
"Well, you certainly have a way of making your, um, clients, feel welcome and relaxed. I didn't think I would feel this way."
"What way?" I asked.
"I'm a little embarrassed," Shelley said, looking down. "But I'm finding myself attracted to you, physically!"
"That's great!" I said, genuinely complimented. "And with that, I think it's time we went back to my place - if you want to."
"I do," Shelley said. "I'd like to be somewhere more private anyway."
We stood and made our way out. The bill would be taken care of later. I'd sent a text to my driver, who was waiting outside in a black limo.
"Hope this is okay," I said, as the driver opened the passenger door.
"I feel pampered," Shelley said, getting in. That was the idea.
I sat next to her, and we took off. The tinted windows of the limo, plus the darkness outside, made it nearly impossible for someone to know where we were going. This was for our safety and the discretion of our clients.
Everything about Shelley was elegant. As she walked up to my house, I noticed a smoothness in her stride. Her ass was splendid, held pretty tightly by her evening dress. I was still amazed this woman could look so good - for being nearly ten years my senior!
Our house is in an out of the way neighborhood that is pretty exclusive. The driveway, and the house, are hidden by trees and large shrubs. By day, it's pretty spectacular, by night very cozy and romantic.
Opening the door, I was pleased that Julie had prepared the space just as we'd agreed. The soft glow of candles filled the front hall and living room, their slightly tropical scent adding a romantic touch.
"This is very nice," Shelley said after I'd closed the door.
Shelley seemed used to the finer things in life. Thus, she could afford our fee. Providing an elegant environment for this elegant woman's first lesbian experience was my pleasure.
"Let's go in," I said, leading Shelley into the living room. Julie had lit a fire, which added its glow to the room. The fire crackled softly.
"Let's have another glass of wine," I suggested. Julie had put a chardonnay to cool on the table, along with two wine glasses.
"Trying to get me drunk?" Shelley asked, smiling and sitting, her knees held together very demurely.
I laughed as I poured our glasses. "No, just to get you relaxed."
Shelley took the glass from my hand, our fingers meeting for the first time. She held the glass just slightly longer than was needed.
"So, how does this work?" Shelley asked after taking a sip. She set her glass down on the coffee table and set her hands on her lap.
"Shelley," I said, putting a hand on hers. "I need you to know that you are in charge. I may be more experienced, but you get to say what you want to do and what you want me to do. This is all about you."
"But I hope you get to enjoy it too," Shelley said, not moving her hand.
"Oh, I will," I replied, smiling. "I'm already very attracted to you."
"Oh!" Shelley said. "So, you've done it, with women, lots?"
I nodded. "I have. Women making love to other women is very special and much different than sex with a guy."
"I'm glad of that," Shelley said. "My ex-husband was more interested in satisfying himself than me."
"Sounds like a
jerk
," I said, emphasizing the jerk part. "Is he why you decided to try lesbian sex?"
"In part," Shelley answered, glancing down. "But I've thought about it for a long time. Several of my friends are bi, some even while still married to men. After conversations about it, I started imagining myself making love to a woman." She looked up at me. "I've even fantasized about it when was alone and..."
"And you've masturbated thinking about being with another woman?" I said.
Shelley nodded. "I just didn't have the courage to act on it until my divorce was final and I was rid of him. By then I decided I needed some, well, professional guidance."
"What do you think about when you fantasize?" I asked.
"Oh!" Shelley said, blushing. "Well, um, I guess I think about a woman's body. You know, the curves and softness and, uh, her breasts," she said, glancing at my chest.
"Sounds delightful," I said. "What else?"
"Well, I picture her - this is sort of embarrassing!" she said.
"It's just you and me here Shelley," I said, squeezing her hand. "I want you to be totally open with me."
"Okay," Shelley responded, visibly relaxing and closing her eyes. "I picture a woman kissing my neck, her hands roaming all over me." She shifted slightly in her seat. "Um, then she starts to undress me - very slowly and sensuously."
This was getting me turned on, and it wasn't even my fantasy!
"Is it all right if we explore that fantasy, here?" I asked gently.
Shelley opened her eyes. Had I broken the spell?
Then she nodded. "I'd like to try that, if you do."
"Why don't you sit back and relax a little bit," I said, touching her arm and encouraging here to lay back on the couch cushions (which are purposefully large and comfy). "Let's also kick off our shoes."
Shelley removed her heels and laid back, still a little stiff, and closed her eyes again. I noticed that her tits were showing through a little more, and her legs were not tightly held together. More good signs.
