Male: Jim –Early 50’s but has the looks and physical traits of a person in his late 30’s; taller than average male, college educated, career appropriated for a college graduate (not hurting for money, owns home, fairly new car, no real debt), very athletic, good health, and fairly friendly person who gets along well with others, few close friends, divorced, no real relationship with ex-wife (can’t stand her) with adult children and several grandchildren, retirement is secured; several short term relationships since divorce, can’t find the right person for his required conditions based upon his taste/needs develop as a result of his marriage, divorce, his realization of what he truly needs to make him happy (true happiness has always eluded him). Occupation – Private Consultant
Female: Ann - mid 30’s, fairly good looking, good figure, tall (5’10”), slightly homely but no introvert, a conservative female in all areas of life; parents deceased, has only one sibling with whom she is not close, several friends but no best friend, currently no boyfriend, has had several short relationships with men (not a virgin) but never married – just can’t find the right person even though she was engaged for a short period of time in her mid twenties, financial well adjusted, home, car etc, not involved with sports, but physical able to play sports if she so chooses. Occupation – mid level executive for a small food company
How they first meet
Jim was on vacation at a resort. He had won a charity raffle, the prize being a week vacation at a topical island resort. He had won the raffle just under a year ago. The time for using the tickets was coming to an end and since he had forgotten about them (he had received a letter just prior to the expiration date reminding that him that the vacation had to be used by the end of the year) he had to go on the trip by himself.
Several tours had been included with the vacation package. The first tour occurred on the day after Jim had checked in to the resort. It was a tour to a secluded lake high in the hills north of the resort. There were enough people going on this tour to fill a medium size school bus. As luck would have it, Jim had to share his bus seat with a somewhat attractive woman named Ann. Jim introduced himself to Ann. She in turned introduced herself and her group of friends (all around the same age) who were seated behind and across the aisle from her and Jim’s seat. This was a friendly group who gladly included Jim in their conversations. Since Ann was without a partner (she was talked into coming on this vacation by her friends who had felt that this type of trip was what she needed at this period in her life) for this vacation, the group encouraged Jim to join their group for this tour to the lake.
The tour guide was a local person who was very knowledgeable about lake and the surrounding areas history. His knowledge made for an interesting trip to and from the lake. The lake formed below a waterfall approximately 20 feet above the surface of the lake. All of the tour group members had been encouraged to bring bath suits so that they could climb up to the top of the waterfall, jump down to the lake and spent some time swimming in the water. The tour included a picnic lunch of food and drinks.
As everyone removed their outer clothing, Jim was rather pleasantly surprised to see that Ann conservative one piece bathing suit revealed Ann’s nice physical shape. Jim being into sports was in very good shape himself. Jim made sure that he was next to Ann during the swimming activities.
Ann was flattered by Jim interest and starting feeling good about herself realizing that this attractive man was paying some much attention to her. It gave her a much needed boost about her physical appearance.
When it came time to eat the picnic lunch provided by the tour, Ann got a meal for herself and one for Jim which she brought over to him. They had a good time talking while eating their lunch. Ann began to feel a real attraction for this man, something that she had not really experienced before to such a degree. On the ride back to the resort, Ann discovering that Jim had no specific plans for the next day, she asked him to come with her group into the town to see the sites. Jim agreed to go alone.
The tour of the town consisted of going to all of the different types of shops where tourist usually spend their money. Again the conversation between the two flowed easily both enjoying each other’s company. As it grew later, the group decided to visit a tavern for dinner. The town had three such establishments, two of the family type of environment and one with a little more adult gentleman’s club type of establishment. One of the male members of the group suggested the adult tavern but his wife and the other wives objected to that. Jim was watching Ann very closely during this discussion and he saw something that further sparked his interest in Ann, he could see that she wanted to go to the adult tavern but didn’t feel comfortable in saying so.
Jim spent the rests of the week with Ann and her group. They discovered that, as fate would have it, they lived roughly within 70 miles of each other in different suburbs of the same city. Just prior to the time that Ann group was leaving the resort (a day before Jim was to leave), she got up the courage to visit Jim in his room. As they sat in the living room sharing a drink (wine for her and coke for Jim who does not drink) she related what a good time she had in his company and hope that they might get together some time in the future. She gave him her phone number. Jim was mildly surprised at her forwardness but accepted the number and stated that he would enjoy getting together some time in the future.
The next day, Jim stayed around the resort resting and thinking about his time with Ann. He kept coming back to Ann’s reaction to the discussion about the adult tavern.
Their First date
One Friday evening, approximately 3 months after returning home from her resort vacation, Ann whose life had returned it normal routine of work and occasionally dating, was home in for the evening. The phone rang and a slightly familiar voice asked how she was doing. As she realized who it was, there was a stirring in loins, it was Jim! He asked her if she remember him and their agreement to get together sometime after returning home. She stated that she did and that she would love to get together and go out. So Jim agreed to drive to her city and to meet her at a restaurant in her part of the town tomorrow night at 7:00 pm.
Ann hung the phone up. She reached down and pulled her long dress up to her waist and placed her hand on the crouch of her panties. They were soaked! Never in her life had she had an orgasm without extensive attention being paid to the various parts of her body. There was a lust in her soul that she never knew could exist and this scared and excited her. Ann spent the rest of the evening going over in her mind the events from the phone call from Jim.
How was she going to deal with these new feelings, return to her old guard self or embrace this new experience? If she did, where would this lead to, how was she to ensure that things were carry out to it conclusion and what did that conclusion entail, or was she to play it safe and continue in her old life?
She came to the realization that she liked these new feelings and wanted to explore them. The question was how to attract Jim while being careful not to scare Jim off by being too forward and eager. She needed a conservative yet appealing start for tomorrow dinner. A newer not so conservative look was needed and that must start with an outfit appropriate for what she had in mind, to marry Jim.
Ann was always a conservative dresser, in public and private (even when alone). Nothing in her wardrobe was specie enough for this first date with Jim. She wanted to ensure that he want to come back for another date. Ann went shopping and bought a new skirt that darling came up to an inch above her knees and a blouse that was just slightly tighter than normal. She thought that this daring outfit would do the trick.
Jim made the long drive to Ann town. He wanted to make it to the restaurant at least 15 minutes prior to the time that they had agreed to meet. Jim disliked being late for anything. He entered the restaurant and requested a table for two, informing the attendant that his party would be meeting him in approximately 10 minutes. He was informed by the attendant that his party was already here waiting for him. This surprised and pleased him.
Jim and Ann had a very enjoyable first date; the conversation was good in that they discovered similar likes and dislikes, and various mutual interests. The evening ended outside of the restaurant. Ann invited Jim to dinner and a movie on their next date which was to be in two weeks. Jim agreed to meet Ann at her house. They parted with a hug and a kiss on the cheek.
Late that evening as Ann lie in bed reminiscing the evening, she discovered that she had been rubbing her clitoris, this surprised and pleased her.
The relationship progresses
Jim arrived on time to pick Ann up at her house. She invited him for a minute while she finished preparing herself for the evening. Jim liked how Ann had decorated her home. When Ann step into the living room both Jim and Ann were pleased with how she looked, similarly to how Ann dressed for their first date but with lighter clothes since the weather was hot.
During the movie, they sat close to each other and at various times even holding hands. At one point, Ann placed their combined hands in her lap generating consider heat in her groin. In the theater, Ann noticed a couple kissing and rather intimately touching each other. Ann was envious of them but was too reserved to initiate anything like that with Jim.
After dinner, Jim took Ann home. At the door, Jim embraced Ann and gave her a gentle good night kiss, which they both enjoyed. Ann was tempted to invite Jim in but again was too reserved to do so. Ann suggested another date next weekend and volunteered to drive to Jim’s home. Jim gladly accepted her offer but suggested because of the long drive that Ann bring an over night bag so that she could drive home the next morning and not have to risk driving that long distance at night. Despite her reservation about spending the night at Jim’s house, Ann felt that his concern for her safety outweigh any concern that he might take advantage of the situation. Jim could sense her reluctance but this was not an issue with him because he had never taken advantage of a woman. His feelings were if a woman doesn’t freely offer herself to him, he doesn’t want it.
When Ann arrived at Jim’s home the following Friday night, she was pleased with his neighborhood and his house. She felt at home and safe in his house.
Jim fixed dinner for them, a good meal that they both enjoyed. When Ann complimented him on his cooking, he stated that he really did not like cooking but always gave it his best effort when he did so for he only did it for special people.
Jim showed Ann around the house. The house was well decorated. She did notice some isolated hooks in the family room and in the guest bed room. She assumed that he had some unfinished modeling in those rooms.
After dinner, Jim had several video that he wanted to share with Ann. They were mainly old movies vintage 1940’s and 1950’s movies (such as “High Noon” and “Sergeant York”, etc) that he had collected over the years. Ann enjoyed the movies and felt that they gave her insight to Jim’s likes and dislikes.
After the movies, Jim showed Ann to the guest bedroom and stated he would wake her in the morning and fix her breakfast. Jim gave Ann a passion kiss and wished good night. He then proceeds to his room and went to bed.
Approximately an hour later Jim was awaken by a presence in his room. He looked up and saw a sexually aroused Ann climbing into his bed. Jim asked her if she really was sure she wanted this and was not overcome by the evening situation. Ann stated yes she wanted this. Jim then firmly stated, “You must ask me have sex with you”. Ann was a little taken back but responded, “Jim, make love to me”.
Their first sexual encounter
Jim pulled back the bed covers and pull Ann into his arms. He tenderly kissed her on the lips for a good two minutes. Jim then moved down to Ann breast spending time on each one sucking, kissing, squeezing, and gently biting them. Moans of appreciation escape from Ann lips. Jim then placed his hand between Ann legs. He found some very soft and extremely wet lips and a nice size clitoris. As he touched Ann clitoris, she moved her hips up in response. Jim then placed two fingers inside of Ann, moving them around in response to sighs and hip movements.
At this point, Ann placed her hand on Jim penis and guided it down to her pussy. Taking the hint, Jim entered Ann and began pumping himself into her pussy; bring her to the edge of an orgasm then slowing his motions until she settled down. Jim kept this up for a long time. When he felt that Ann couldn’t possible take any more sensual pleasure, Jim increased his pumping speed until Ann exploded into a very strong orgasm. Jim quickly emptied all of his semen into Ann womb which caused Ann to pass out.
Jim then held Ann in his arms for several minutes until she recovered her senses. Ann then kissed Jim tenderly on his cheek and nestled her face into his chest.
After several minutes Ann got up to go to the bathroom with the intention of reliving herself of the sperm in her pussy and to pee. After taking care of that, she returned to Jim bed and his arms to fall asleep.
Ann was in a deep peaceful sleep, like that she rarely experiences. She began to slow awaken because her pussy was felling wet and warm. She awoke to find Jim face in her pussy. After her initial surprise, Ann relaxed and for the first time in her life, she completely let go of any control over her body and completely surrender to Jim’s oral manipulation of her sexual organs, breast, pussy, her butt, and her anal cavity for Jim was foundling and liking all of them.
After bring Ann to a tremendous orgasm, Jim enter Ann and exploded inside of her. After gaining her senses, Ann started to get up to relive herself, but Jim stopped her. He told her to stay there and to let his some of his sperm run out of her and let the rest to stay in her pussy. Ann first thought was that was unclean and started to protest. Jim pointed out that they had just given themselves to each other and the liquids in and leaking from her vagina was a symbol of that. The longer they remained in her the longer the experience actually last. Ann had never looked at it that way, she relaxed and stayed in Jim’s arms falling into a gentle and peaceful sleep wanting feeling this afterglow of their sexual sharing every time she felt more liquid seep out of her.
Ann awoke around 10:00 am in the morning finding herself alone in the bed. Reaching down to her vagina Ann felt the dry mixture of her fluids and Jims sperm mixed in her hair and on her legs. A smile formed on her face remembering that this meant that their love making was still continuing. Ann got up to go the restroom. She looked for something to put on but her clothes were not in the room. Looking around the room, she could not find anything to put on. She heard some cooking noises coming from the kitchen. She called out to Jim but received no answer. Having no alternatives, Ann got up and went to relive herself wearing no clothes. Afterwards, she reluctantly went into the kitchen where she saw Jim wearing a robe, fixing breakfast.
Upon seeing Ann, Jim invited her to sit at the kitchen table so he could serve her breakfast. Ann asked Jim where her clothes were. He stated that he put them away. She then asked him if he had another robe. Jim replied that the robe he was wearing was the only one in the house, but she could earn it use by doing “the required task”. Ann asked what “the required task” is. Jim’s reply was “to drink her morning milk”. Ann asked “where is the milk”. Jim replied by walking directly up to Ann and opening his robe which allowed his rock hard penis spring out in front of Ann lips.
Ann was taken back and thought about her choices, to stay nude or to suck Jim off and get the robe. Ann felt self conscious about sitting there nude and decided she wanted the robe. She then open up and reluctantly took Jim in to the depth of mouth. As she suck on Jim, Ann became intensely aroused by the thought of what she was doing, sitting nude in a house that she had never been in before, sucking a penis. Ann was overwhelmed lust and within a minute she had “drank her milk”!
Jim removed the robe and handed it to Ann who then placed in on the back of her chair. Upon seeing that, Jim stated it was his turn to drink his milk. Jim slowly moved Ann’s chair back, got on his knees and lick Ann vagina lips opening her total up for his viewing pleasure. He then moved to her clitoris licking and sucking on it until Ann exploded in an orgasm that flooded Jim face with her “milk”. Ann knelt down so that her face was level with Jim and licked his face clean.
They did have the breakfast that Jim fixed. At that point Ann stated that she had to return home (it was not true but she was overwhelm with the events last night and this morning and needed to go home and reflect on these events). Jim gave Ann her clothes and watch as she dressed not offering or insisting on Ann cleaning herself up because he wanted her to leave with all of the odors of their loving making on her body. He wanted her to smell them and to think of him.
As Ann drove, she frequently pulled her blouse away from her neck and sniffed the odors on her body. The drive was pleasant and uneventful.
Ann as entered her home, she kept her promise and called Jim so that he knew she was safely home. She removed all of her clothes and put on a robe which she remained in until early Monday morning when she took a bath and prepare to go to work. She could not get enough of the odors on her body.
Jim leads Ann into a new sexual awareness
Jim and Ann talk several times during the next couple of weeks. They agreed that Jim would make the drive to Ann town for their next date. Jim would arrive at Ann home early Friday evening and they would go out for dinner.
Jim arrived at Ann’s house half an hour early, traffic had been light. Ann answer the door wearing a robe, she had not finishing dressing. She brought Jim into her living room, stating she needed a little more time to get ready. 15 minutes later, Ann entered the living room wearing a nice looking combination of a loose hanging skirt that came down to just above Ann’s knees and blouse. She looked very nice and rather relaxed, ready for a good evening. Jim remained seated and asked Ann to come over to him. When she did, Jim lifted her skirt and looked at her panties. They were full panties. Jim very quietly informed Ann that when she was with him that he would like it if she could wear either the briefest thong panties or no panties at all. Ann felt that familiar heat rising between her legs, since she had no thong panties, she step back from Jim, removed her panties and slowly presented them to Jim nose. Jim took in a deep breath. Ann then threw the panties on the couch and walked to the front door. Ann had never felt so bold in her life.
Jim took Ann to a musical play that they both enjoyed. As they left the theater for the outdoor parking lot, the wind starting gusting, pushing Ann’s skirt up toward her waist, which she quickly grabs the skirt pulling it down. Jim, of course, was watching this with great pleasure. Jim open the car door for Ann and as she was entering the car, the wind again whipped up blowing her skirt up to her waist exposing her for all to see. Jim closed the door and when around to the driver side and got in. Ann looked at him with her face red from blushing, saying that she hoped that no one saw her. Jim then responded by pulling her skirt up to her waist, stroking her clitoris and stated “I saw at least two men with big smiles on their faces looking in your direction”. Ann sighed and sat back against the car seat with a slight smile on her face as Jim droved out of the parking lot.
Jim not feeling ready to have the evening end asked Ann if you want to go and get a drink (even though Jim does not partake himself). Ann having similar feelings, stated that would be a good idea and directed Jim to a bar on the oppose side of town from her home. The place was frequent by a younger crowd of people. The bar was crowed with a good mixture of diverse female and males. The music was good and everyone seemed to be in a good mood. The only place that they could find a seat was at the bar.
After a couple of drinks, Jim excused himself so he could go to the men’s room. Ann stated that she would be fine by herself. Upon returning, Jim notice that Ann had turned on her stool to look at the large crowd of people who were happily dancing. Jim was pleasantly surprised to see Ann sitting with her dress high up her mid thigh with her legs spread apart facing the dancers. Remembering that he had removed her panties, Jim was aware that anyone looking in her direction was being treated a clear view between Ann’s legs. As Jim sat next to Ann, who was still facing the dance floor, Jim said “if you want to give everyone a better view, you should have a clean shaven vagina”. Ann smiled and turning back to the bar saying that she would consider doing that. Shortly thereafter, they left for Ann house and some great loving. All evening during sex, Ann kept thinking about the men looking at her naked waist. She felt a new release of some hidden inhibitions which increased the pleasure of her love making with Jim.
The flowering of Ann
For the next three weeks while Jim was out of town, Ann had plenty of evening and weekends to think about her relationship with Jim and the changes in her that had occurred during this relationship. She was going over in her mind her new sexual awareness and her boldness in opening showing herself to strangers in the parking lot and especially at the bar where it was her doing it as opposed to the wind blowing up her skirt. Was she being too bold or sluttish? Did she really like those feelings or was it just the excitement of the moment?
On the second weekend without Jim, Ann accepted a date from a former boyfriend, Bill, that she still had a good relationship with. Bill took Ann to a very popular play that was currently in town. They both were into plays, so Ann did not feel that going with Bill would present any problem with Jim. She intended to tell him about going out with Bill. They had not at this point in time established an exclusive relationship between them. Besides, Ann had never been physical with Bill beyond some light kissing and touching.
Ann was always very thoughtful in the clothes she wore and her apparel for the play would not be an exception to her care in her appearance. Ann had pick a silk cream color dress that was cut modestly low in front and the bottom came just above her knees. The dress was form fitting and really accented Ann nice figure. Over the dress, Ann would ware a coat.
As Ann was taking a bath in getting ready for the evening out to the play, one of her hands starting stroking the lips between her legs while the other found her clitoris. Ann remembered Jim’s statement “if you want to give everyone a better view, you should have a clean shaven vagina”. Ann had never completely shaven between her legs. Yes, she trimmed the hair down there so that it looked neat and well kept but never totally nude. Ann got up from the tube and got her razor and some cream. Returning to the tube, Ann proceeded to cream everything from her anus to the top of her pubic hair. This was an extremely sensual experience. Using the razor, did a very nice job of sharing. She liked how it felt when she ran her fingers over her lips and how beautiful her sex looked.
Ann finished her bath and got dressed for the evening. About 10 minutes later, Bill arrived to pick Ann up for their evening out. Ann went to the front door wearing a light robe over her dress and invited Bill telling him that she had to get her purse. Ann went into her bed room. As she removed the robe, she looked at herself in a mirror, feeling wonderful and sexy as she reached under her dress and removed her panties. Putting on her coat for the evening she went out and joined Bill stating that she was ready to go.
After being seated in the theater, Ann rose and removed her coat, letting Bill for the first time see her evening dress. Bill remarked to Ann, how lovely she looked in that form fitting dress. Bill realized that Ann had never worn a sexy dress before in his presence. Bill was quite pleased, thinking that Ann had dress that way for him.
As the play performance preceded, Bill notice Ann’s dress riding up her legs. He also noticed that Ann frequently crossed and uncrossed her legs, which caused the dress to ride further up her legs. Uncharacteristically, Ann made no attempt to pull the dress down. During the intermission, as Bill passed Ann to go to the restroom, he got the shock of his life as he looked down straight into Ann clean shaven vagina. Needless to say, Bill made great haste in returning to his seat treating himself to another look up Ann’s dress.
On the drive home from the theater, Bill became advantageous and placed his hand on Ann exposed thigh. Not receiving an objection from Ann, Bill continued to rub Ann leg during the entire trip to her house. Bill was thinking that this was going to be his luck night with Ann. When they arrived at Ann’s door, Bill held Ann directly in front of him giving her a deep kiss. Ann openly responded to the kiss. They continued kissing for an entire minute. Getting real bold, Bill slipped his hand down to the hem of Ann’s dress, raising it enough for him to stroke Ann’s vagina. He then slips in finger into Ann. At that point, Ann removed Bill’s hand; bring it up to his mouth and sticking it in. Ann asked Bill if he like the taste. Upon receiving an affirmative response, Ann then said thank you for a very nice date. Confused, Bill asked if he could come in and continue the date. Ann responded, “That as much as I can give you, for I belong to Jim”. Ann then walked into her house closing the door leaving a confused Bill wanting more.
Ann never felt so alive in her life. She liked this feeling of power, sexiness and even though she in her heart of heart knowing that she belong to Jim that she could be so bold and open with her sexiness to whom she feel like doing these things with. Ann slept really well that night even though she longed for Jim’s return so she could share this evening’s event with him. Ann thinking seen how excited Jim got when she had exposed herself to the men at bar a few weeks ago; she was sure he would like what she had done.
A week later, Ann answered the phone and upon hearing Jim’s voice, her vagina open and fluid began flowing down her legs. Jim was calling out of state during a hold over while waiting for his transfer flight home. Ann asked Jim if it would be possible for him to change his flight so that he could land the airport in Ann’s home town. If he could, Ann would pick him up and they could spend the evening together and in the morning she would drive him home. Jim thought that was a good idea and he would immediately check on making the change in his flight. About 10 minutes later, Jim called back with the news that he was able to get the last seat on the flight to Ann’s town. He would arrive in 2 hours.
Two hours later, Ann greeted Jim in the baggage pickup area. Ann wore a dress that had buttons in the front from the bottom of the dress all the way to the top which end slightly below the top of Ann’s breast. The top button was undone as well as all of the buttons from mid thigh to the bottom of the dress. As they hugged, Jim could feel Ann unbridled breast against his chest and his right hand past smoothly over Ann poster uninterrupted by any form of panties.
As Jim held open the drivers door of Ann’s car as she sat in the driver’s seat, Jim was treated to the beauty sight of Ann’s open and wet vagina. As Jim and Ann had not spoken during Jim trip, they had a lot of catching up to do. Jim couldn’t really go into his trip, due to the nature of his employment, but Ann was anxious to tell Jim about her date with Bill. She wanted to know if it would excite him, for she felt that Jim would understand, agree with and except this type of behavior from her. Ann wanted the right setting so she waited until they were in bed together.
As they were lying naked in each other arms, Ann told Jim that she wanted to tell him about the events of last Friday night. But she would do so only if Jim would go down on her. Jim agreed. Ann began from the beginning, Bill calling and asking her out. She explained how even though she was “now with him” that going out excited her because of the new world of sexual awareness that Jim had opened up for her. She now feels free to do/explore this new world of feeling and senses. So as Ann went into the events of her date with Bill, Jim really began to please Ann orally as he became more excited about the changes in Ann. Jim was so excited that at the point of date where Ann let Bill taste her on his finger and then stated that she belonged to Jim, Jim raised himself up from eating out Ann, pointed his penis at Ann stomach and came like he never did before. Seeing that, Ann had a tremendous orgasm herself. Their mutual coming so exhausted them that Jim clasped upon top and Ann. Due to Jim fatigue from the trip and the late hour of the night, Jim then fell off into a deep sleep. Ann laid there feeling a sense of freedom she never knew existed. She was Jim’s yet she could do what she wanted because belong to Jim was a choice not a requirement and she knew that Jim wanted and would ask for certain things and behavior from her but he would never force anything upon her. She had to freedom to give those things to Jim. Ann then fell off to sleep herself, neither of them awaking until the next morning.