“Are you awake,” I asked.
“What time is it?” was her sleepy response.
“A little past 9:30,” I told her.
If we hurried we could make the hotel breakfast which ended at 10:00 a.m.
“Can’t we just have room service send up some coffee?” she said, offering more of a suggestion than posing a question. I rolled over, found the phone and called room service.
Back under the covers, I asked how she was feeling.
“Not bad, considering. My ass doesn’t hurt as much as I imagined it would, and my pussy is just a little sore. It’s my nipples that hurt.”
“I’m sorry,” I said.
“No, don’t be sorry,” she said, “It’s a good hurt”.
She also had rug burns on her knees, as did I.
I told her how much I had enjoyed our first evening together, and that launched a discussion of the prior evening’s events.
“Where’s my list?” she asked.
Even without seeing the list, we both knew that we had made a big dent in Gail’s “weekend wish list”.
We talked for a while, and of course, being a guy and reliving our sexual activities the night before, I was soon aroused.
“Mmmmm,” she said. “I see you’re getting interested again in the weekend’s topic. Can’t you control that thing?” she joked. “It poked me in the back all night.”
Gail took hold of my shaft, massaging it as it grew in length and girth.
She had surprised me. Her favorite thing from the night before was not the anal sex we had worked so long at accomplishing. Nor was it that mind blowing orgasm she had during the anal sex. No, her favorite thing from the previous evening was being teased.
Maybe it was the novelty of our weekend. Or maybe Gail was already hot and horny when we arrived at the hotel room. Whatever the reason, she said that she loved being teased and was interested in exploring that subject again as the weekend progressed.
“It’s a new day,” she said as she held onto my cock. “What have you got planned?”
“Coffee,” I said, just as there was a knock on the door.
I put my robe on and answered the door. Gail buried herself under the bed covers.
A waiter rolled a cart into the room with the coffee and a newspaper. If he noticed Gail’s black thong on the floor, her bra hanging on the desk chair, her vibrator on the coffee table or the two big feathers on the bureau, he didn’t let on.
I signed for the coffee, found my pants and some money and gave the guy a good tip.
Gail emerged from the covers and put on her robe. After fixing her hair, she joined me for breakfast.
We sipped coffee, ate a sticky bun or two, and read sections of the newspaper.
The hotel lunch started at 11:30 a.m. I told Gail that I was going to shave and suggested that she look over her list and pick some activities for the afternoon. When we had dressed, we could look over the hotel facilities and then have lunch.
I went to the bathroom to shave.
I took off my robe, splashed hot water on my face, and spread lather over my morning beard.
Gail walked in, sans robe, her tits bobbing side to side and up and down.
“I have some ideas,” she said, as my manhood grew once more.
“Want to talk about them now or over lunch?” she asked, acting coy and bashful.
She leaned against the sink and reached down and held my semi-erect member in her hand. Slowly stroking my cock, she teased me a little.
“Watch it,” she said. “I wouldn’t want you to cut yourself.”
Now wanting to play, Gail squatted down, took my cock in both hands, and proceeded to slide my now fully erect member into her warm mouth.
“If you don’t stop,” I said, “we are going to miss lunch.”
She stopped sucking and licking long enough to say, “So, we miss lunch.”
“We need to get out of the room for at least a few minutes so the room can be cleaned and the beds made, and you may want to pick up and hide a few things,” I reminded her.
“Alright,” she said, releasing my erection from her lips.
“When do I get to play?” she said, pouting as she left the bathroom.
We explored the hotel lobby, the indoor pool, the gift shop, the bar, and the pub in which I had grabbed a quick dinner the night before. Poking our heads out the hotel’s front door, we quickly confirmed that the heat and humidity still hung over the City.
We at lunch in the hotel dining room, taking care to be seated far enough away from others so we could talk.
It was a buffet lunch, and when we had gone through the food line and sat down, Gail was eager to talk.
“Can we take some pictures this afternoon? Will you teach me how to tease a guy? What do you want to do?”
Taking pictures of Gail and having her pay attention to my cock for the afternoon seemed like a good plan to me.
Teasing became the topic at lunch; I did most of the talking. Gail absorbed anything and everything I said. If she had a pencil and paper with her, I’m sure she would have taken notes.
From my experience, before Gail got to practice teasing on a guy, she had to understand a few things.
Teasing is the art of making your partner feel as wonderful as possible for as long as possible. To be able to do that, without letting your partner cum, takes both knowledge and talent.
The most important thing Gail would have to learn is to be able to recognize when her partner was ready to cum. The idea, I told her, was to bring her partner right up to the point of orgasm, but not let him go over the edge, and to do that as many times as possible without letting him cum.
The guy may beg and plead, but she must not give in. In the end, the longer she can tease her partner, the greater will be his reward.
It is a task easier said than done.
Some women innately know how to tease; others need to learn. For those who must learn it literally takes practice and more practice.
When we got back to the room, I asked Gail to assemble all of the toys and put them on the coffee table, while I got the camera ready.
There were two cameras. The digital camera I said I would bring and a digital video camera that I had grabbed at the last minute.
Gail was eager to test her teasing abilities; to play with the toys we had brought; to see how long she could keep me from cumming; and maybe even to see if she could make me beg for release.
The toys were on the coffee table; I spread my robe over the sofa chair and sat down; and, Gail got on her knees on the floor between my legs.
She sat back and looked at my cock. “That is very impressive,” she said. “Exciting, impressive and a little scary.”
Sitting in front of a lady who is admiring my manhood and preparing to make love to it, I got that wonderful feeling of chills throughout my body; part pleasure and part excited anticipation.
My shaft stood erect, straight and swollen, waiting for her touch.
Gail wrapped her long, manicured fingers around the shaft. She played with it for a minute, licking at the enlarged head, kissing it, and lightly stroking my shaft. Then she took the head into her warm mouth.
I settled back, closed my eyes and let her work her magic.
I had promised to show her some teasing tricks, ideas, and techniques that she could use.
Her mouth worked on the shaft and head bringing me spasms of pleasure. If I didn’t stop her wonderful sucking, I’d soon shoot my gooey sperm and there wouldn’t be any lessons.
Although I had never had them used on me before, I directed Gail to start with the big feathers.
Holding one in each hand she ran them lightly over my balls, up and down the shaft, and across the head. It tickled, in a sensuous, erotic way, and made my cock twitch.
Tickling my cock with feathers was not going to make me cum, but it was an intense pleasurable feeling. My cock pulsated and jerked with each soft stroke of the feathers, causing pre-cum to dribble out and run down the side of my hard shaft.
Adding to the pleasure was watching Gail lightly stroke my cock with the two feathers and the look on her face. Clearly, she was one of those ladies who enjoyed teasing, and the pleasure she was getting from tickling my shaft and balls only gave me more pleasure.
I handed her the silk-like scarf. The scarf had multiple uses: it was a blindfold; a restraint; something to wrap around the shaft while giving a hand job; and it was also a useful toy for teasing a lady.
For now, I had Gail drag the scarf over the head of my cock, which she did very again and again. The silk-like material is just rough enough that the sensation of the material sliding over the head of my cock was both pleasurable and almost unbearable. It’s not likely to make a guy cum. Nonetheless, it feels wonderful, and is an effective visual and sensual teasing tool.
I showed Gail how to wrap the scarf around the base of my cock. If she held onto just a corner of the scarf and slowly pulled that corner straight up, the silky material would slide in circles around and up the shaft as it uncoiled. Do that a few times and see if the guy doesn’t love it and ask for more.
The black glove was similar to that worn by a woman to a social affair. Stroking the shaft and head of a cock with a gloved hand provides a different texture and feel, and pleasures similar to the scarf.
It may be that the hair brush is a much more useful tool for teasing a lady; certainly the hair brush handle had proved useful the night before. Nonetheless, running the soft bristles over the shaft of my cock and balls felt very good.
The hair brush should not to be used on the head of the guy’s cock, which is way too sensitive for the bristles on a hair brush, even though the bristles may be soft. The same goes for use of the bristles on a lady’s clit.
I showed her two other techniques, both of which should be part of a lady’s teasing arsenal. Each, however, must be used sparingly.
I had her take the shaft of my cock in one hand and pull down on it, stretching the skin on the head of my cock. In this way, what is a very sensitive area anyway, the swollen head of my cock, becomes even more sensitive.
Gail could then just suck on the head, but only the head.
Or, with her fingers and some lubrication, she could run the tips of her fingers and fingernails around and over the head.
Or, forming a “ring” with her index finger and thumb around my shaft just under the head, and with a little lubrication, she could move the “ring” up and down, stroking just the head.
Concentrating like this, just on the sensitive skin on the head of his cock will make a guy cum very quickly; very quickly.
But quick is not the goal in teasing. Use this technique sparingly.
In order for a lady to be good at teasing, she must be able to tell when a guy is close to going over the edge. Observe his breathing, body movements, and facial expressions, and listen to the sounds and noises he makes. With practice, a lady will know when to stop or slow down, and not let her partner cum.
Gail, much to my pleasure, wanted to experiment with each toy several times before moving on to a slow, pleasurable hand job.
I would tell her when I was close to the edge, and she would slow down or stop. Then she would begin again until I gave her the sign that I was again close.
We repeated this routine several times until it became increasingly difficult to tell her how close I was.
Her hands and my cock were covered in pre-cum. And, the pre-cum that was oozing out was even mixed with a little cum.
I was close; in wonderful agony and ecstasy; and was ready to explode.
With both hands, Gail lightly, slowly, sensuously kept stroking my cock and running her fingers over its swollen, sensitive head. Her eyes alternately focused on my eyes and on the little slit at the tip of my cock, watching to see if she had gone too far.
“Do you want to cum?” she asked.
“Does it feel good?”
I told her that I was ready and would not last much longer.
“Say please,” she said.
“Please. Please. I need to cum.”
She lowered her mouth over the head of my cock and began to slowly suck on it, staring into my eyes.
It took only a few seconds of her warm mouth on my cock before I erupted.
I had warned her; I told her that I was going to cum. But she kept the head of my cock in her mouth. She wanted to swallow.
I shot streams of hot cum into her mouth, much of which she could not swallow.
Cum flowed out of the corners of her mouth and over my cock, while she fought not to choke.
She looked up at me, still milking my cock of its prize, and smiled as cum ran off her chin in long threads onto her breasts.
She was excited, having enjoyed the whole experience.
I was drained.
Gail didn’t need any more lessons from me.