———————
"I don't like this idea, Amy. We always said our first times would be with each other. Why do you want to change that?"
"All of my girlfriends had bad experiences their first time. At best, it was awkward and unsatisfying. For Beth, it was actually painful. I want my first time to be amazing, but neither of us knows what we're doing. If you had some experience you could teach me. Would you please do this? Please? For me, Billy?"
"It just seems weird. I want to be with you, not your mom. How did you even think of this crazy idea?"
"I thought our first time together would be better if you could lead me, but that meant you had to know what to do. I thought of how you could get some experience and two ideas came to mind. You could sleep with one of my friends, but they'd talk or try to steal you from me. Plus, they don't really know that much anyway. I also thought of hiring someone, but aside from being illegal, we don't have the money."
"Wait a minute! You considered hiring a prostitute?"
"Only for a minute. They certainly have experience, but like I said, there're problems with that idea."
"Yeah, quite a few, including that I would never agree to that. I'm not even sure I can do it with your mom."
"Well, I thought of her when I was at my wit's end. She's actually perfect. She has experience, she definitely won't tell anyone, I trust her not to steal you, and it's not illegal."
"But it's really weird."
"I've thought a lot about this and it's the best solution. She loves me and will make sure you know what to do. She understands the situation and . . ."
"Hold on! You've already talked to her about this?"
"Yeah, I had to make sure she was willing before I mentioned it to you. Plus, I wanted her opinion on the whole situation."
"What'd she say? How'd she react?"
"She was shocked at first . . ."
"I can imagine."
"But she understood my concerns and wants my first time to be great. She said hers wasn't and wants mine to be better. She finally agreed. Now it's up to you. Will you do this for me, Billy? For us? I love you so much."
"I love you, too, which is the only reason I'm considering this. It's a lot to take in, but I want our first time to be special."
"Please?"
"Okay, I'll do it. How will this work?"
———————
That's how I found myself at the Williams's home at 7:00pm, about to have my first sexual experience at eighteen years old. Amy had told her mom that I agreed to this odd plan and a time was set for a Friday evening when Amy would spend the weekend at her friend Beth's home and my parents were out of town for the weekend. I was incredibly nervous and still apprehensive about the whole arrangement when I rang the doorbell.
"Hi, Billy, come on in."
"Hi, Mrs. Williams."
"It hasn't been ‘Mrs.' Williams since I divorced my cheating husband a year ago. And, please, call me Lori. I think that's more appropriate given why you're here, don't you?"
"I guess so."
"Would you like a soda or a glass of water?"
"Yes, please, some water would be great."
"Have a seat on the sofa and I'll be right back."
Lori returned from the kitchen with two glasses of water and sat close to me on the sofa. She looked beautiful in a tight pair of jeans and a plain white blouse with buttons down the front. As she tucked her bare feet under her, she tried to calm my obvious nerves.
"I know how anxious I am about this evening. I'm sure you must be a little uncomfortable also."
"I am. I thought my first time would be with Amy. I'm worried that I'll do something wrong and that I'll disappoint you. You have so much more experience, I'm surprised you're nervous."
"The pressure's all on me precisely because I have more experience. You've probably anticipated this moment your whole life. You've heard stories from your friends and maybe watched some porn. I want to meet your expectations and I want to teach you well enough that you make my daughter's first time a positive experience. That'd be enough pressure even if it hadn't been over a year since I last had sex."
"You haven't had sex in more than a year? I'm sorry. I shouldn't have said that."
"It's okay. Sex is better when there's open communication between partners. That's my first lesson for you, I guess. Never be afraid to ask questions. I expect you'll have many this evening. Also, it's important to tell your partner how you feel and what you want. We'll practice all of this later.
"As to my break from sex, I wasn't feeling very sexy or even attractive after Amy's father cheated on me. I know it's a cliché, but it still hurts when your husband finds his twenty-year-old secretary more attractive than you. Christ, she was born the same year we were married! I know my forty-three-year-old body isn't what it was when we were young and dating, but a life together and our wedding vows should've counted for something. After his rejection, I didn't have the courage to put myself out there in the dating scene and face more rejection."
"I can't believe he or anyone else would reject you. You're a beautiful woman with a killer body! I'm sorry, that just slipped out. I've embarrassed you and made you blush."
"Don't apologize. That's the nicest compliment I've received in a long time."
Lori leaned in and gave me a brief, soft kiss on the lips. When she pulled back slightly, she stared at me with mesmerizing, pale blue eyes. The moment seemed to last forever as we both thought about what we would do next and whether the evening would proceed as originally planned. With unspoken agreement, we each leaned forward and began a longer, more passionate kiss.
As our mouths opened and our tongues first touched and began to play, I reached out to wrap my arms around her. In turn, she placed her arms around my neck and pressed her large tits against me. It was electrifying and I lost all hesitancy about the evening, wanting to continue kissing this woman and learn all that she had to teach.
After a minute, she broke the kiss and repositioned herself so that she straddled me, clearly taking charge. She held my face gently in her hands and renewed our kiss, probing my mouth more deeply with her tongue. I ran my fingers through her long blonde hair, and periodically stopped kissing her mouth to kiss her neck or nibble on her earlobes. These actions seemed to excite her and she cooed as she wiggled on my lap before resuming our kissing more aggressively.
"Why don't you take off my blouse?" she asked between kisses.
I pulled it from her jeans, slowly unbuttoned it, and slid it from her shoulders. Displayed only inches from my face were her magnificent tits. As beautiful a sight as that was, I wanted to see the treasures encased in the cups of her lacy white bra.
"Can I remove your bra?"
"I hoped you would take the initiative. That'll be important when you're with Amy."
I reached behind her and fumbled with the clasp. She smiled at my difficulty.
"You haven't done this many times, have you?"
"Never."
"Really? I assumed that you and Amy would've gone at least this far."
"No, we were always afraid that if we did more than just kiss or rub each other through our clothes, we'd get so worked up that we couldn't stop."
I finally succeeded with the clasp and removed her bra, revealing a perfect set of tits. I couldn't help but stare at the first naked tits I'd ever seen in real life. She smiled at my wonderment.
"Go on and play with them. This evening is all about you learning how to excite a woman. You certainly already know how to kiss, but there's so much more you can do to give her pleasure.
"Start by just lightly stroking my tits and areolas, the circles surrounding my nipples. Ah, that's nice. Now also massage my tits, gently but firmly. Oh, I like that. While you're massaging them, kiss them, but don't go immediately for the nipples. Build some anticipation. Kiss the tops and sides. Lift them up and kiss underneath them. Women love that and most men neglect that area."
I was doing as instructed and Lori seemed to be really enjoying herself when I stopped abruptly.
"I see you found my scars. The plastic surgeon did a great job with my breast implants and the scars are not very noticeable, but they are there and visible if you look closely. And you're certainly looking closely," she smiled. "Do they bother you?"
"No, I just find them interesting. It also explains why your tits are so much bigger than Amy's. She said she's a 32B. How big are you?"
"36D. I was naturally smaller like Amy, but her father wanted me to have larger tits and constantly commented on it. Three years ago he finally talked me into it. That should've been a clue that I wasn't enough for him. In any sense, I guess," she joked. It was good to see that she could at least laugh about it.
"Well, they look great, but I definitely like Amy's smaller tits also."
"You should make a point of telling her that. She thinks they're too small and is self-conscious about that. That's another lesson. Women are often not satisfied with their appearance, however they look. Complimenting them not only makes them feel good, but relaxes them, and being relaxed is critical for great sex."
With that I resumed my kneading and kissing of Lori's tits. When I thought the time was right I began to also lick and suck on her nipples, mixing in light strokes. She certainly seemed to enjoy that, moaning softly and thrusting her tits at my face.
"You can also bite my nipples and pinch and pull them, but not too hard, especially at first. While most women enjoy some nipple play, how hard varies, so it's best to start out gently and see how she responds. You can also scrape her nipples with your teeth, but nipple play in general is another area where communication is important."
I practiced all of these new techniques at length, with Lori offering words of encouragement throughout.
"Ooo, I love what you're doing. That feels incredible. Twist my nipples harder. Squeeze my tits. Flick my nipple with your tongue while you bite it. Oh, you're so good at this."
Lori's vocalizations increased in volume and frequency, and her squirming became more constant. Her nipples had hardened and become erect in my mouth as I sucked on them and continued my play. As her breathing increased, so, too, did her utterances.
"Just like that. Keep going. Don't stop. Yes. Yes. Yes. Yes!"
Suddenly she stiffened and cried out.
"Ohhhh. I'm cumming. Uh. Uh. Uh. Uh. Uh."
Her body shook in violent spasms and she threw her head back. I held onto her to keep her from falling off the sofa and her chest was flushed. Slowly her spasms became twitches and then she was still, leaning her face against my chest. We sat quietly like that for several minutes, with me not knowing what to say or do and not wanting to break the spell.
After several minutes, Lori leaned back and looked at me with those same mesmerizing eyes, only now they were moist with silent tears.
"What's the matter? Did I do something wrong?"
"No," she quickly assured me. "Absolutely not. I'm just so happy. A man hasn't given me an orgasm in several years, and I've never cum just through nipple play. It was a new and amazing experience. I didn't realize until just now how much I missed a man's touch. Thank you."
With that she kissed me passionately, but with a tenderness we had not shared previously. She stood up and reached for my hand.
"Let's go to the bedroom where we'll be more comfortable. I owe you an orgasm," she smiled, "and you have more lessons to learn, but you're a quick study and it looks like I'm really going to enjoy teaching you."
To be continued . . .
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