Summer Of Regrets

Ann had a deep and rather dark secret. After 15 years of marriage, the guilt of what she had done still ate at her. Both Ann and Don were Catholics, brought up with the belief that sex belonged in marriage only. They met in December of their freshman year of college. Neither of them was special, Ann at 5'3", 34a-26-35, glasses, was very smart, but plain. Don at 5'9", 135 pounds, also very smart, was awkward with girls and not very experienced. Ann was even less experienced, having kissed one boy in college and none in high school before meeting Don.

They hit it off immediately. With so many things in common, they could talk forever. Even their different majors, his in engineering, hers in sociology, were not a problem because they could share and understand so easily.

With that kind of friendship, sexual attraction was automatic and they shared many deep kissing sessions before the Christmas break. Even though they lived somewhat near ear other, in Olympia and Tacoma, the time apart was agonizing for both.

Spending so much time together, they naturally progressed in their kissing sessions until one night their mutual passion had him on top of her as she opened her legs to feel his hard, but unseen, penis against her vulva and especially her clitoris. She climaxed that night and wondered if his heavy breathing meant he had also. After that, dry humping became a regular part of their activities and even though Don had never yet touched her breasts, she had many times felt her skirt or dress ride up as he rode against her exposed panties or pantyhose crotch.

Over the summer and the next year, the touching increased, much to Ann's pleasure and guilt. Although by the end of their sophomore year their dry humping had occurred completely naked several times, they still maintained their determination to be virgins until their wedding day, if it should come. Most people looked on Don and Ann as a couple that would of course marry on graduation.

The summer between their junior and senior years was the one where they had to be apart all summer. Don's engineering internship was going to take him to near Indianapolis for the entire summer. Ann took a job at the college for the summer session. This allowed her to stay in the dorm with a friend who was a nursing student. It also allowed her to be with other nursing student friends during their summer school session. Besides, Ann thought Portland summer weather was much nicer than Olympia summer weather.

Don left for his internship one week after school got out for the summer. They wrote to each other almost daily and were able to talk on the phone once a week. With this, the first few weeks of summer before the start of the summer session passed without too much pain for Ann.

The summer session was harder. This was where they had spent so much time together, exploring their sexuality. Ann worked at the school switchboard and kept her time filled fairly well during the week, but weekends were harder to bear, except for the all too short calls from Don each Saturday or Sunday.

After two weeks, two nursing student friends, Cathy and Terri, suggested Ann go to a party at a nearby house. Cathy told Ann, "You can't just sit around here missing Don all summer. Get out and have a little harmless fun."

The party started at 5 and it was a very warm summer day. Ann chose to wear her newest summer dress and sandals. The dress was sleeveless, mid-thigh, high waisted, with a tie back. Ann enjoyed how the dress felt on her in the hot weather and thought she looked good in it. Green was a good color on her, the flowers made it even more feminine.

The party was a semi-typical college type party for the early 90s, and people mixed, talked, played games and drank beer or wine as they enjoyed chips, hot dogs and hamburgers. Ann felt out of place at first and did not know who to hang around with or what to do. Cathy and Terri had almost immediately separated to be with guys they had clearly planned to meet at the party. Ann could not help but notice that neither girl minded the fact they were not their regular boyfriends.

Then Tom came up and said hi to Ann. Tom was maybe 5'10", 23, nice looking and friendly. His manly scent didn't hurt any either. Ann enjoyed his attention and they began to talk. Tom talked about his job as a security guard, family and adventures while Ann talked about her college classes, Don, family and what she liked to do. Ann found herself attracted to Tom and allowed him to bring her food or wine and teamed up with him for some games. Cathy noticed Ann and Tom together and told her to enjoy his company.

As it began to get dark, Ann noticed Cathy and Terri leaving in Terri's car with the two guys they had met. She turned to Tom and said, "It looks like I am going to need a ride back to the dorm." Tom said, "No problemo, I would be more than happy to give a pretty girl like you a ride."

Half and hour later Tom suggested maybe Ann might be ready to leave. As Ann got into Tom's Malibu, Tom asked if she minded if they stopped by his apartment so he could get his jacket. Ann told him she didn't mind.

Tom's apartment was not far away and Ann got out of the car to go in with him. While Tom was getting his jacket, Ann noticed his VHS collection and was reading titles. Tom noticed Ann's interest and asked if she wanted to watch a movie and have some more wine. Ann saw the movie Coming to America and decided she wanted to watch it.

Ann settled on Tom's couch as she put in the movie and got out some wine and glasses. Then Tom settled near her. As the movie progressed, Ann and Tom inched nearer to each other, then Tom put his arm around her. Ann felt comfortable with Tom, again enjoying his manly smell and his firm body as she relaxed against him.

As Ann leaned her head against Tom's shoulder he pulled her closer and then leaned over and kissed her. The feel of his lips on hers and his tongue exploring her mouth were delicious. However, as he moved his hand to cup her breast she said, "Please don't."

Ann felt she was keeping things under control as she enjoyed Tom's kisses. As they continued to kiss, Ann settled lower on the couch, vaguely aware her dress was riding up as she did so. Tom pushed Cathy back on the couch and so she was laying down with him half on top of her. She could feel his very hard manhood against her upper thigh and hip and thought about how good Don's hardness felt against her clitoris when they made out.

Ann's legs spread almost involuntarily and Tom just naturally slipped between them. Ann felt his penis rub her clitoris and didn't try to stop Tom as he again massaged her breast through her dress. The intensity of Ann's feelings increased and then she suddenly climaxed. At almost the same time, Ann was sure she could feel Tom's penis pulse against her and was pretty sure he had climaxed too.

Ann held Tom against her as he relaxed, then said, "Please let me up." Tom moved off her and she sat up, straightening her dress, which she noticed had slid up almost to her waist. Then she asked Tom to take her back to her dorm. Tom asked, "Are you mad at me?" Ann assured him she was not, but she was filled with confusion as she said it.

At the dorm, Tom walked Ann to the door and kissed her tenderly.

The next day was Sunday and Don called. Ann told him of the party, but left out the part about Tom, other than to say she had met a guy named Tom and enjoyed talking to him.

On Wednesday, Tom came by the switchboard when Ann was working and asked if she wanted to join him for pizza nearby. Feeling lonely again, Ann decided there was no harm in it and told him she would be ready at 6.

Deciding what to wear was hard. Ann finally decided on a short sleeved shirt and shorts. Tom picked her up promptly at 6 and immediately kissed her before leading her to his car. Dinner was nice and Ann didn't mind at all going back to Tom's apartment for another movie.

This time they sat together on the couch and as they kissed Ann did not object as he put his hand first on her breast and then inside her shirt gently squeezing her nipple. However, Ann stopped him when he tried to put his hand down her shorts. Instead they ended up laying on the couch again and her legs opened to feel him stimulate her. As she felt Tom's hard penis rub her clitoris, Ann couldn't help but wonder what it looked like and how it compared to Don's. She also found herself wishing she had worn a dress or skirt. Her climax felt good and she wondered if Tom enjoyed it as much as she did.

Things went like this for two weeks, with Tom managing to take things just a little further each time. Still, he had not gotten his hand inside Ann's panties yet. However, on their second Wednesday date he did get his hand under her skirt.

As Tom dropped her off at the dorm and kissed her goodnight, he asked Ann if she would go to the zoo with him on Saturday. When she agreed, Tom asked her if she would wear the dress from the party two weeks before when they met, saying, "You look so good in that dress, Ann."

Saturday morning Ann was nervous as she prepared for her date with Tom. She felt guilt about enjoying his attention, but didn't want to stop the good feelings she had from her time with him. Thinking about how high her dress had ridden the first Saturday, and turning red, Ann chose her prettiest panties to wear under the dress.

The day at the zoo was fun. The weather was perfect, mid-eighties but with a light breeze that felt good under Ann's dress. Tom held Ann's hand most of the time and had his arm around her waist the rest of the time. His random kisses felt good again and Ann thought guiltily about how good it would feel to have him on top of her again, especially when they kissed in a secluded area and Tom cupped her butt under her dress as he pulled her into him.

When they got back to Tom's apartment he got out a frozen pizza which Ann put in the oven as he got himself a beer and a glass of wine for her.

After dinner Tom again suggested a movie and Ann chose Love Potion No. 9. As they watched the movie, Ann wondered what her relationship to Tom was. He was not at all like Don, yet she was enjoying his company and his attention.

As the movie progressed, Tom slipped his hand inside the top of Ann's dress and she enjoyed how it felt and how it made her feel all over. After a while, as they kissed, Ann felt Tom's hand on her leg and moving up her inner thigh. She again felt confusion as she thought of moving his hand, but also thought about how good Don's fingers had felt inside her and how good Tom's hand felt high on her inner thigh. Her legs opened enough his fingers reached her panties and she caught her breath as he stroked her clitoris.

Tom then undid his pants and Ann could see the top of his penis pushing against his underwear and noticed the wet spot there. Still when Tom tried to remove Ann's panties she stopped him. Deciding to distract Tom, Ann straddled him and enjoyed the feeling of his penis rubbing her with only his underwear and her panties between them. She did not object as Tom lowered his pants and underwear, kicking them off. The feel of his penis so close to her vagina was so good as she felt it push her panties between her labia.

Tom picked Ann up and took her to his bedroom, laid her on her back and settled between her legs again. Again Ann felt the tension and then release and she climaxed. This time she knew she felt the pulsing of Tom's penis as he came all over her panties.

Tom was immediately apologetic and got some tissues to wipe himself and to wipe his semen off Ann. As Ann watched Tom wipe his penis off, she noticed the wet area on her panties was getting cool and decided she needed them off to properly wipe them. Pulling her dress down, she stood up and removed her panties as Tom watched, careful to make sure he didn't see anything. Then sitting carefully on the bed, Ann wiped her panties and pressed them between two tissues.

Tom watched Ann and then kissed her again. Again his kisses felt good and Ann allowed herself to be pushed back on the bed again. As Tom put his hand on her breast again, Ann felt a tingle in her clitoris and spread her legs slightly. Tom continued to kiss her and then slowly moved half way on top of her then completely on top of her and she spread her legs again.

This time there were no panties between Tom's penis and Ann's vagina. Ann was a virgin, but Tom was not. Tom's penis felt incredible between Ann's labia and felt even better as he rubbed the head right up against the opening of her vagina. Ann knew she had to stop, right now, but didn't want the good feelings to end. Still she told Tom to keep the tip of his penis up higher.

As Tom and Ann kissed, he again slid down her body slightly and Ann could feel the head of his penis between her labia at the opening of her vagina again. She didn't say anything and didn't try to stop Tom as he slowly slid into her. The feeling was incredible as his penis passed between her inner labia and pressed against where her hymen should have been. Ann noticed a slight pain as Tom pushed forward and then he was fully inside her and she could feel his balls against her.

Tom slowly moved in and out while sometimes pressing all the way in as she rocked her hips to move her clitoris against his pelvis. Ann's breathing became heavier as her state of excitement increased. Suddenly, she felt her entire body tense as the muscles of her vagina contracted around Tom's penis deep inside her. The feeling was like nothing she had ever felt before as she found out what was missing from dry humping.

As Tom began moving in and out of her again, Ann thought of their complete lack of protection. She didn't want him to release inside her, but she also didn't want the feelings to stop. Suddenly Tom drove deep inside her and with a grunt of pleasure, began spurting his sperm laden semen deep inside. Ann was amazed at how good his pulsing penis felt in her as she felt him release. Again, it was like nothing she had ever felt before.

Tom lay on top of her as his penis softened and came out of her. Tom rolled over and Ann sat up on the bed. She had never felt like this before, but couldn't believe she had allowed it to happen with someone other than Don. Tom reached for a couple of tissues and handed one to her as he wiped himself off. Ann suddenly realized Tom's semen was coming out and wiped herself off.

As Ann stood up and straightened her dress, Tom asked her to spend the night. Ann was seriously tempted, but decided she needed to get back to the dorm. She asked Tom for her panties and put them on, this time not worrying about keeping her dress down as she pulled them up and adjusted them. Finding her sandals in the living room, Ann put them on and asked Tom to take her back to the dorm.

As Tom walked Ann to the door, she wondered about her feelings. Did she want him to kiss her goodnight? Did she want to see him again? What about Don?

Still, as Tom kissed her goodnight he asked when they could see each other again. Ann told him to call her.

Ann entered the dorm and walked down the hall to her room. She was glad her roommate was away at home for the weekend. As she passed Cathy and Terri's room they asked where she had been. She just said, "Out." Cathy and Terri both said, "Ohhhh, I see." Ann felt herself blush and wondered how obvious her no longer a virgin status was.

The next day when Don called Ann was hesitant and wasn't sure how to respond when Don said, "I love you." She finally said, "I love you too." Then Don had to bring up marriage. It was what she wanted, and yet, she felt like she had ruined everything. She just said, "Don, I don't know if we are ready." Don replied, "We will talk about it, but when I get back I want to announce our engagement. I miss you so much." Ann said, "I miss you too. I love you."

Monday, Tom asked Ann if she wanted to have dinner with him on Tuesday. Ann said yes and thought about what she might wear. She finally decided on a short denim skirt and t-shirt to meet him. This time Ann had no doubts about where the date would lead and did not hesitate as Tom led her to his bedroom where they shed their clothes and got in the bed. When she got back to the dorm Cathy commented on how much time she was spending with Tom and asked if she was getting serious about him. Ann told Cathy they were just friends.

Friday, Tom again asked Ann to go out with him and she spent the night with him. Her third through sixth times having sex occurred before she returned to the dorm the next day. Cathy asked Ann where she had been and she just turned red.

Ann continued to see Tom at least a couple of times a week, sometimes spending the night. She was greatly relieved when her period came and resolved to be much more careful. Toward the end of the summer school session Tom asked Ann to spend the weekend with him at the Oregon coast. After the weekend Ann wondered what her feelings for Tom really were. She knew she didn't really love him, but their times together were sure good.

Don returned from Indianapolis a little over a week before school resumed right after Labor Day Weekend. Ann realized her love was for him and when he proposed again she accepted.

Ann was pleased to show off her engagement ring with the half carat stone to all of her friends. Cathy was also engaged to her boyfriend. Terri, on the other hand, had broken up with her boyfriend and was now dating the guy she had been seeing during summer school. Cathy and Terri shared secrets with Ann and Cathy assured Ann she understood about her sleeping with Tom during the summer since she also slept with the guy she had been seeing. Ann realized that Cathy and Terri just assumed she had lost her virginity to Don before then and did not attempt to correct the misunderstanding.

Still, try as she might, Ann could not get Don to have sex with her before the wedding. She missed the feeling so much she started seeing Tom again a couple of times a month. This had to be done more discretely, but Ann now had a her own car at school, so she could meet Tom at his apartment. They even managed a couple of weekends together when Don was away.

Ann and Don got married in June of 1995, after graduating in early May. Ann was thrilled to finally be having sex with Don, but was silently disappointed when he came too soon after entering her the first time. However, he made up for it the next try and they settled down to an active and orgasmic sex life as they made their life together in Portland.

Yes, Portland, and there was the problem. Fifteen years later, even following Tom's marriage and divorce, after Ann's three children, she was still seeing Tom at least once a month.