When I checked my mailbox on the adult dating site, there was a short message from a woman named Ann.
She was 30, living in Cambridge, MA, just across the Charles River from Boston, new to the adult site, and would be interested in chatting.
I acknowledging her email, indicated that it was nice to meet her, and asked her about herself; at least whatever information she was willing to share at this early time.
She wrote the next day. She was originally from Seattle, was single, worked in Cambridge, and would be interested in mature, adult discussions about sex.
I told her a little about myself and asked her to be a little more specific about her interests.
There followed a half dozen email exchanges through the adult site in which we each related some of our sexual experiences and interests.
I suggested that it would be easier to “talk” if we used our personal email instead of going through the adult site, and provided her with my email address.
She responded the next day with her email address, and we continued with our discussions about the joys of sex, toys, positions, and really anything that jumped to mind.
In one email, Ann just said, “Call me,” and provided her telephone number.
I called her that night, thanked her for her number, gave her a little scolding about giving out her number to a complete stranger, and did my best to “educate” her about how she needed to protect herself when dealing with others on-line.
We spoke by phone almost every night.
One thing that has always intrigued me is what happens along life’s way to cause a lady to realize that she likes sex. Not that she just likes sex, lots of women do, but what happened in her life to make her realize that she actually and genuinely really likes sex and wants to experience all that sexual relationships have to offer.
Ann had what I would call a “normal” sex life. In high school there were a couple of steady boyfriends with whom she explored some of the joys of sex, mostly bare tit, nipple play, hand jobs and fingers in her pussy.
On a class trip, she was preparing to go out, and was standing in front of a bathroom mirror, fixing her hair, and dressed only in panties. The bathroom door was open.
One of her male classmates mistakenly thought the bathroom was empty, walked through the door, scaring Ann, who turned around and faced the young man.
Her classmate just stared at her bare boobs for a few seconds, apologized, turned and left the bathroom.
In those few seconds Ann learned what intense pleasure she would feel when a man looked at her body. She had a specific memory of realizing at that moment that she wanted, and more than that, needed to experience that pleasure again.
In college she lost her virginity in her freshman year to a guy who really had little idea of what he was doing, learned how to give a decent blow job, and even experimented a couple of times with another woman, all of which just whetted her appetite for more sex.
In graduate school, Ann had another experience that cemented in her mind that she loved sex and that she wanted to explore, learn and experience everything that a sexually active life could offer her.
She lived near the campus with her boyfriend at the time. The sex was good, and the two regularly fucked three or four times a week, sometimes more, and sometimes more than once a day. She had no complaints. He satisfied her, and while she did not orgasm every time, she did cum many times. But these were just orgasms; nice, and satisfying, but not the powerful, mind blowing experiences that she had read about and dearly wanted to experience.
There was always this nagging sense that there was more sex to experience and enjoy.
Ann came home late one Saturday night, very horny and needing some male attention. Her boyfriend and two of his friends were sitting in the living room watching football. Judging by the number of empty beer cans, the three had been drinking for some time.
Upset that her boyfriend was in no shape to satisfy her sexual needs, and more interested in football and his buddies than her, she went to her room.
She was upset, needed a man’s touch, and decided to take a risk that she would not have ever considered even a few months before.
Ann undressed, put on a bath robe, walked confidently out into the living room, stood in front of the television and let the robe slip off her shoulders and onto the floor.
The three young men stared at her body, and Ann felt herself shake with pleasure. This time, however, the pleasure of being looked at naked, exposing her tits and pussy to three men, was almost overpowering. Instantly she felt her pussy become wet and was very much on the verge of having an orgasm.
The three guys just stared at her and said nothing. It was at that point in her young life that Ann realized the full power of being an attractive woman with a nice body and how much she could play with a man’s mind and cock without ever even touching him.
Now not knowing what to do, she boldly told the three to “jerk off” for her. At the time, it was all she could think of saying. One by one they dropped their pants, grasped their erections and started to stroke their cocks as Ann walked closer in front of them, pulling on her nipples.
She recalled that the sexual feelings she had at the time were overpowering; waves of pleasure swept through her body.
Ann’s boyfriend was the first to pop, spraying his cum onto the small coffee table, after which he slumped over, and either went to sleep or passed out, with his limp dick dribbling cum onto his pants.
Then things got a little out of hand.
Ann moved closer to the other two, and said, “Who wants to fuck me?”
The words, however, were spoken before she even realized that she had said them.
Right away, she had mixed feelings. Standing in front of two guys her own age, watching them look at her pussy, and her watching them stroke two sizable cocks, had emboldened her to want more.
On the other hand, she couldn’t believe she had said what she said, and wasn’t sure what would happen next.
Her expectation was, of course, that these two guys, whose names she didn’t even know, and who been stroking their cocks for several minutes, each would just cum, she’d enjoy watching them cum, the expressions of their faces, and the noises they would make, and then her risky bit of fun would be over, and she would take care of her own needs back in her room.
Paraphrasing something someone once said, “The best laid plans (no pun intended) can often go awry.”
Neither guy shot his load. Instead, both took off their pants, and before she could react, Ann was on her knees. Soon, one had his shaft in her slit and the other had his in her mouth. She was being fucked by both guys at the same time in front of her “out cold” boyfriend.
Yet, there was no sense of panic, no saying stop and no concern that her boyfriend was there. To her own amazement, Ann quickly and willingly became an active participant, pushing her love hole back against the guy doing her from behind, taking in his entire shaft, while devouring the other guy’s manhood in her wet mouth.
The guy with his cock in her mouth came quickly, bending back and grunting loudly, as he filled her mouth with streams of cum which Ann just let dribble out of her mouth and down her chin.
The guy fucking her doggie lasted a few more minutes, but shot his load all over her ass and back with a loud groan.
When they were done, the two just put on their pants and left, leaving Ann still on her elbows and knees, cum drooling off her chin in strands and streaming off her ass and down her legs onto the floor
Instead of it being a traumatic event, Ann, although a little dazed, thoroughly enjoyed the experience.
She reached back and shoved three fingers into her sopping wet pussy and brought herself to a huge orgasm, one of the best she had ever experienced. And, she didn’t stop. Slamming her fingers into her slit and against her clit she brought herself quickly to a second, just as intense, orgasm.
It took Ann a few minutes to recover, but she eventually got herself up, noted that her boyfriend was still “out” with his limp dick slumped over to one side, and walked to her room, cum on her lips and dripping from her chin and running down her ass and thighs.
There was a slight, but satisfying smile on her face.
She was pleased with herself, having satisfied two guys at the same time and having experienced something new. The thought was now permanently planted in her mind: what else is there to explore?
After graduate school she worked in the Seattle area and then took a job all the way across the country in Cambridge, MA.
Work took a lot of her time, even requiring evening and weekend time. Dating and meeting new friends were put on the back burner. Her sex life, with the exception of “Ted”, her vibrator, was non-existent.
Now she had been promoted and had more time for herself. A girlfriend in her office told her about the adult dating site. She observed the site for a while and then joined.
Rather than deal with all the messages that came to her from guys telling her how much the sender wanted to fuck her or what they would do to her, she ignored them, and sought out guys on the site who were local and seemed interesting and contacted them.
That is how we met.
Eventually, we exchanged photographs. Ann’s wasn’t a flattering photo. It was a head and shoulders picture which was used on her security badge at work.
I never learned what Ann did for work, or her last name, for that matter. All I knew was she was Ann from Seattle, and that whatever she did for work required a security clearance and badge.
She was about 5 foot 4 inches tall, much more attractive than her security badge photo, and had an athlete’s, fit body with perfect sized boobs. She had long black hair with large curls down over her shoulders and back. If I had to compare her to someone familiar, she was a much thinner Monaca Lewinski of Bill Clinton fame.
She suggested that we meet.
Having told her how she should protect herself when dealing with on-line strangers, I suggested that we meet on a Saturday morning, at an outdoor coffee shop at Faneuil Hall Market Place, a very public place.
She was already at the coffee shop and seated, when I arrived. I introduced myself, sat down and we had coffee and made small talk.
The small talk led to more discussion about each of us, and morning coffee turned into an afternoon lunch.
After lunch, we walked through the city, across the Boston Common and Public Gardens, crossing over to the Esplanade and the Charles River and the walkway along the Charles River to the Massachusetts Avenue Bridge which connects Boston and Cambridge. Along the way we sat on the river bank grass and continued our discussion.
She was a very intelligent and attractive woman. We seemed to get along well and the conversation flowed naturally, always absent any awkward moments.
At the Bridge, Ann had to say goodbye so she could get home and get ready for an evening event to which she was committed. I hailed a cab, paid the driver, saw her off, and walked home.
We spoke by phone during the week and met again the next Saturday, this time for lunch, followed by another walk along the Charles River.
We sat along the river bank and Ann told me the above two stories. She also asked some pointed and personal questions. How many women had I had sex with? Had I ever been involved in a threesome or more? What was my favorite position? Had I ever done anal?
I also asked her questions, which she answered without hesitation.
Each question was asked without any awkwardness or embarrassment by either of us and answers were followed by more discussion on that particular subject.
Other than what she had related about her boyfriend and his two friends, Ann had never participated in any planned threesome, but she was interested. She liked being on top, on her side, or doggie. She was interested in anal sex. At least on the right day, in the right mood, and with the right guy, she would consider it. Sex outdoors was of particular interest as well as playing with cum or at least having a guy cum on her body where she could rub her fingers in it.
For the time being, she was looking for a friend with benefits; someone with whom she could explore her interests in sex, try things she had only read or heard about, and at the very least satisfy her sexual needs when release was needed.
It started to rain. We ran under a tree whose branches spread out all the way to the ground. Underneath the branches we were protected, dry and alone.
I took the chance and kissed her. She didn’t back away. In fact, within minutes we were locked in a hot embrace, tongues battling. Her body pressed against me and I could feel her breasts push into my chest. My manhood grew and I hoped that she could feel my cock pressing against her.
When the rain had stopped, we walked to the main road and I hailed another cab for Ann to take home. I told her how much I had enjoyed our talk and our kissing, and we made plans for another lunch.
I was beginning to really like this lady. Being “friends with benefits” was certainly something I was interested in, but with this particular lady, I was hoping that it might lead to something more serious.
A week later, after more telephone calls and lunch at a restaurant in Cambridge, Ann wanted to show me something; a place she had been to once and wanted me to see.
We took a cab to Brookline, got out on a corner street, walked by a few stores, and then down a driveway to a small, below ground store in the back; a sex shop Ann had found that had a funny, but appropriate name: “The Back Door”.
We walked around the store, the only visitors on this Saturday afternoon. We spent an hour or so in the store, with a few other couples and some singles eventually coming and going during the hour. Ann ended up buying some scented oils; I bought a small vibrator, partly out of guilt from being in the store for so long and having not made a purchase, and partly as a clue to Ann that I was very willing to be her friend and enjoy her benefits.
Outside, we lingered on the sidewalk, not saying much, and experienced our first real awkward moments of silence.
“Want to go to my place?” she asked.
We walked to a main street, hailed a cab and went to her apartment in Cambridge.
Ann had a first floor apartment in a triple-decker. There was an open living room-dining room area, large bedroom, and a large kitchen and bathroom, and all with beautiful wood floors.
We sat on her living room couch and looked over the vibrator, putting the batteries in, turning it on, and feeling the buzzing tip.
“Want to try it,” I joked.
“I’ll bet you’d like that,” she joked back, putting the vibrator back in its box and walking into the kitchen.
“I certainly would,” I said to myself.
“I’ve got lots of food. Want to stay for dinner?”
It was still early, around 3:30 in the afternoon.
I said, “Yeah. I’ll stay for dinner. Can you cook?”
I walked into the kitchen and put my hand on the small of her back. She turned into me and we kissed. And then we kissed more. And then we got to the living room couch and made out like two teenagers in heat.
At some point during one of our passionate kisses, Ann took my hand and placed it on her breast. I squeezed her breast through her sweater and she let out a little moan.
I took her hand and placed in on my hard cock, now stretching down my pants. She squeezed my shaft and ran her fingers over it.
Ann got up and went over to the windows and drew the shades. When she came back, she straddled me on the couch, gave me another tongue lashing kiss and said, “We’re going to have sex now, aren’t we?”
“I’d like that,” I said.
“On the couch or in the bedroom?” she asked.
“It’s up to you,” I said. “It’s your place.”
“I like the couch. We’ll see where it goes from there?” she suggested, her voice shaking a little with anticipation and excitement.
As Ann removed her sweater, exposing her bra and breasts, she reminded me that for her it had been some time since she had had any sex and asked me to go slow.
When she reached behind her back and undid her bra, two large tits fell out. They were a little big for her frame, but not overly large, and they stood straight out. Her nipples were red and beautiful, about the size of a half dollar and already hard. With her hand, she held one of her breasts up to my lips so I could lick and suck on her nipple.
“Do you like that?” she asked.
