Jennifer and Harry Pt. 01bybrowngrad©
Jennifer is fairly typical of most Midwest, middle class, middle aged women. Born and raised in a small northwest Indiana town, she enjoyed a stable upbringing and attended the local University to obtain a degree in English literature. She married her high school sweetheart, had two wonderful children with him, and enjoyed their lovely home.
Sexually, she had a rampant imagination but low on courage. When she turned 40, she realized that she wanted more out of life with regards to her sexuality and passions. Her husband, Tom, was a good man who provided well for his family. Between the two of them, they enjoyed a comfortable life. He was the first man she ever did anything sexually with and that remained so until her trip to London meet a man she had fallen for over the internet.
On the Monday before she was scheduled to leave for London, she arranged a cyber-date with her prospective lover. As she waited for him to come online, she reflected on the guilt and selfishness she felt at arranging to leave the country to meet this man. She found herself thinking about her sexual history, and recalled the first time she and Tom were sexual together.
She flashed back to their senior year in high school when they were madly in love with each other. Jennifer wanted to have sex in the worse way. Most of her girlfriends were sexually active but she felt very conflicted about losing her virginity before marriage. Tom was one of the guys in high school that all the girls admired. He was an A student and one of the top players on the Tennis team. When she and her girlfriends went to his tennis matches, they all giggled and squirmed when he came out in his tennis shorts. He was 6'2", 185 pounds of solid, supple young man. It made her angry that her girlfriends were lusting after her boyfriend, but she refused to give in to peer pressure. One of her girlfriends was frankly a bitch, and threatened to fuck him if Jennifer did not give him a blow job on their next date. Of course, that ended their friendship.
Tom loved and respected Jennifer. Despite his yearnings, he did not want to compromise her values. Although dates with her typically ended with passionate kissing, there was no other sexual activity other than the usual masturbatory fantasy about her once he returned to the isolation of his shower at home.
She recalled them going off to college and keeping in daily contact. She remained at home to take advantage of the excellent education her local university offered, while he traveled to the larger State University some 150 miles away. During their freshman year, they finally began exploring their sexuality together. She recalled secretly traveling to see him over homecoming weekend. Her parents thought she was caught up in homecoming activities, but really, she was many miles away hoping to lose her virginity to the man she loved.
She recalled the excitement as she drove to see him. "Tonight is the night that I become a woman," she thought to herself as she arrived at his dorm. He was a resident counselor which carried the perk of a single room. She recalled the feeling she had at seeing him after being apart for about six weeks. He needed a haircut, but otherwise was remained tall, handsome and athletic looking as ever. She recalled the flush feeling in her face and the embarrassment she felt at compulsively glancing at his crotch. He made the college tennis team as a freshman, and just returned from practice when she arrived. His athletic shorts did not hide much of what she would later discover was an 9 inch god send.
She recalled the awkwardness of not know how to proceed with what she knew she wanted. By default, Jennifer fell into the familiar pattern of kissing him and hugging him. Tom felt free to finally explore her body, reaching down to massage her firm bottom. As he did so, she jumped and gasped softly at the feel of his cock pressing against her firm body. Her mind was flooded with fear and excitement. She waited to take Tom's lead. As he moved away from her embrace, he was proud to show off his now fully erect cock through his tennis shorts. He asked if it was alright for them to take off their clothes and with that, they stood naked and wanting. She recalled the feeling of innocent excitement as she noticed that Tom could not take his eyes off of her breasts and erect nipples. She became very sexually excited by the thought that she was desirable to him. She could feel an unfamiliar transformation taking place in how she viewed herself. For the first time in her life, she no longer felt like a dumb virgin high school girl. She basked in the feeling of being a woman in heat. Jennifer cautiously reached out to rub his chest. She held her breath as her hand moved down to tease his navel while planting gentle kisses on his neck. Reaching further down, she touch his penis for the first time.
It was the first cock she ever touched in her life. She was amazed at how smooth and powerful his shaft felt. She could not believe that the head of his cock was as swollen as it had become. She stood in front of him gently stroking his cock, discovering and exploring his penis. She never imagined that the feel of a man's penis in her hand could be so pleasurable to her. Bravely, she asked him to lay on the bed and silently, she examined his body.
She began by straddling his thighs while facing him. She was well aware of her exposing her vagina to him as she positioned herself over his legs. She could feel her vaginal lips parting while she stroked his rock hard erection. She was gentle at first, but when he reached up to fondle her breast, she squeezed his cock tighter and stroked it with a firm grip. She wondered if he had cum already since his cock was glistening with a sticky slimy fluid. She recalled reading an article in a magazine about pre-ejaculate, and figured that the fluid was a sign of his excitement. She recalled being surprised by her boldness and by the sudden urge to possess his penis. She also recalled the feeling of inadequacy as she compared her little inward vagina to his massive ripe cock. She wanted to stroke him until he exploded and she recalled wanting to feel that explosion as if it was hers.
As she continued to be lost in thought, she relived the memory of moving further up his body placing his cock between her legs so as to make it seem like it was her cock and she was jerking herself off. She leaned back a little and with a fury unlike she ever imagined, she stroked "her cock" with all she could muster. With that, she recalled Tom throwing his head back in total surrender. She recalled feeling his body tensing up.
While sitting at her computer waiting for her on-line lover, she shuttered at the excitement she felt when she witnessed his huge load of semen coming out. It flew up in the air and startled her. Almost at the same time, they both exclaimed, "holy shit"! She recalled the embarrassment that they both felt. On his part, he seemed sheepish and apologetic about the semen that was now deposited all over his chest and stomach. On her part, she was afraid that he thought she was some sort of sex freak who secretly wanted to be a man. With a disappointed snickered, she recalled how they got dressed, went to the school snack bar for a burger and fries, and never spoke about the afternoon encounter.
That recollection shook her back to reality. She had been so lost in thought that she failed to notice that her British cyber lover had been trying to instant message her. During their internet chat session, she spoke of the excitement she was feeling by the thought of secretly going to meet him. He asked many questions about her sexuality, her preferences, and her relationship with her husband. With the memory of her first sexual interaction with Tom fresh in her mind, and through the chat session with Harry, she discovered what was lacking in their sex life. She recalled feeling horribly frustrated that they did not have intercourse on his homecoming weekend. She also recalled the now familiar feeling that the sexual encounter was all about his orgasm. "Well...," she typed, "he seems content to have me stroke his cock and to fuck me, but he does not really bring me to orgasm." She went further, " I'm ashamed to say, but our sex life is rather boring and routine. I masturbate every morning after he leaves for work and enjoy the sexy feeling that comes with wearing thong underwear and tight fitting pants to the grocery store or to the mall. I can literally feel the men undressing me as they stare at my ass."
Harry was obviously very experienced in sexual matters. He spoke of the things he enjoyed sexually, things that she could only imagine. During one particularly steamy chat session he articulated all the things he wanted to do to her. He taunted her with the possibility of being with a man who enjoyed bringing a woman to the heights of sexual pleasure. He then made a request of her. He asked that she call him during one of her morning masturbation sessions and manipulate herself to orgasm over the phone. He was very specific in his request. He only wanted her to identify herself and then play with herself until she had an orgasm. She thought she could do that and arranged a time for the phone call.
She began the morning of her phone call by taking a nice long soak in the hot tub. She felt most sensuous in the morning. Tom was off to work, the kids were gone for school, and she finally had private time to so as she pleased. She often masturbated shortly after everyone was off to school. On warm days, she cleaned the house in the nude.
The privacy fence around her hot tub allowed for her to enjoy a naked 30 minutes of fantasy and pleasure. She enjoyed the feeling of the steamy water on her skin. Closing her eyes, her mind drifted to thoughts of her cyber-lover. The picture he emailed her depicted a ruggedly handsome man. His large, muscular body stood in sharp contrast to the sensitivity of his words on her computer screen. He tended bar for one of the trendier nightclubs in London and had a passion for rugby and opera. Her mind drifted to the fantasy of her being his wife. She fantasized about waiting anxiously for him to return from the championship match he told her about a few nights ago. "Oh my," she thought to herself, "I can see him walking through the door, dirty, sore, battered and bruised from a hard match. I have nothing but my robe on when he walks through the door. I'll let him know that I have been keeping a bath warm for him. I'll help him take his clothes off, kiss him with a wanting kiss, and invite him to let me bath him." The thought of it cause her to throw her head back and spread her legs ever so slightly in the hot steamy bubbling water.
In her little hot tub fantasy, she so wanted to prompt him to lie back in the tub while she stood behind him, running her fingers down his chest, massaging his well muscled shoulders. She could practically see his penis breaking the surface of the bathwater. She visualized herself running her fingernails down his chest, gently pinching his nipples and of course leaving the washing of his genitals for the very last. Her mind fast forwarded to her holding his soapy cock in her hand while she stroked it with one hand and cupped his balls with the other.
The intense fantasy together with being in the hot tub a little longer than usual made her slightly lightheaded. She went inside to enjoy a fruit salad, and bottled water followed by a glass of her favorite white wine. It was now going on 10 am and she was already starting to get beside herself in lust and passion. As she put the breakfast dishes in the sink, she impulsively reached through her satin robe to rub her aching pussy. She ran her finger along the length of her vaginal lips, poked a finger in ever so slightly, and then pulled away, determined not to allow release until it was time for her phone call.
Before making the call, she wanted to review some of his recent emails to her. In one, he spoke of his lust for her and his wish that she could travel to Britain to make love with him. During his most recent email, he wrote descriptively about wanting to give her a full body massage. He described rubbing her back and using his fingers to release the tension from her spine. He wanted to take her hands in his and use his thumb to trace forceful circles around her palm, followed by a light tracing with his finger up her arm and ending with teasing circular touches around her nipples. He went so far as to fantasize about using a feather to lightly brush her vagina until it opened like a flower hungry for moisture and sunshine.
The time had come, and not a moment too soon. By now, she was practically jumping out of her skin. She wanted desperately to talk with him, and fill him in on the numerous erotic thoughts she had about him over the course of the morning. She also wanted to please him by obeying his request that she only identify herself and then proceed to climax. She laid back on her bed, gently massaging her breasts. The "girls" perked up right away. She reached down to gently trace light touches around her genitals with four of her fingers, running light circles around the heat of her desire. With that, she hit the speed dial and when he said hello in his sexy British accent, She uttered, "Mmmm, hi lover, its me Jennifer."
She proceeded to hit the speaker button and intensified her manipulation of her genitals. She breathed heavily while pressing harder along the outside of her vagina. She moaned as she paused from the genital manipulation to squeeze her breasts together. She then wanted desperately to have him hear the sounds she makes when she is in that gray area between pain and pleasure. She licked her fingers to that he could hear it over the speaker phone, making it a point to slurp loudly so that he could easily surmise what she was up to. Then, in very uncharacteristic fashion, she moistened her anal sphincter with her wet fingers. When her anus was wet and fairly relaxed, she plunged two fingers into her now receptive opening. She was surprised at how easily her fingers slid into her receptive asshole. As she did so, she let out the sexiest deep sigh that she could muster. She was now out of control and tightened her anal sphincter to squeeze her fingers while rubbing her fully engorged clit with her other hand. While panting and moaning with pleasure, she began to feel the waves of orgasm coming on. They were like crashes of thunder and lightning on a warm summer night. First came the crackling sounds and then the boom. She pulled her fingers out of her ass and rubbed her clitoris furiously. Suddenly , she felt an unfamiliar sensation. She yelled, " Oh my god!" and with that a large amount of vaginal fluid erupted from her vaginal opening. She giggled and gasped , exclaiming, "Oh shit, I just had my first squirting orgasm."
As she laid on the bed, spent and still trembling with the after effects of the most intense orgasm she ever had in her life, she whispered, "Have a good evening, Harry, wish you were here."