From Good Girl to Grand Slam

We also discussed my early concern that her renewed interest in sex might extend beyond our relationship. I acknowledged that I had seen no signs of that in the past several months. Julie seemed quite surprised with that statement and quickly assured me that she had absolutely no interest in sex without me. She was equally surprised when I asked her if the "MILF" would consider the possibility of going beyond just teasing other men with my encouragement and presence.

Julie's quick response was, "No, I haven't even considered being with other men."

I equally quickly rejected that answer, "Julie, Of course you have, when I talk about other men lusting after you or wishing they were fucking you, we both get very excited. Everybody fantasizes about other people."

Julie conceded that she did find the fantasy of being with other men exciting. But she still felt guilty about even thinking of enjoying sex outside of a loving relationship. As much as she had some second thoughts about not having more sexual experiences when she was younger, she very much felt she made the right choices. Her discipline ensured her of a great education, supportive parents, great career, finding me, having a wonderful family and other choices that might not have otherwise been realized.

No regrets for previous choices but also no regrets for the experiences of teasing me and other men and certainly no regrets for our more active and adventurous sex life the past few months.

These discussions extended over several sessions as we shared feelings and then explored the answer to my question on the possibility of going beyond just teasing other men with my encouragement and presence. I left Julie with the challenge of identifying under what, if any, conditions she would be willing to take the next step. A week after that question was put to her she responded with a carefully thought out list of conditions:

•It can't involve anybody we know, it must be anonymous.

•He must be attractive and charming.

•No drugs and not more than a couple drinks. This must be done with full mental faculties.

•I must be in her immediate presence 100% of the time.

•It should be in another town to ensure nobody we know is aware of it.

•If she changes her mind or says no to anything it will stop immediately.

•It needs to be incremental, like when we were in school: first base - kissing, second base - making out, third base - genital fondling, home plate - sex. A few days after each experience we will see if we are both still comfortable with proceeding after sober reflection.

•I must have professional assurances that the person is clean and healthy for steps beyond second base.

After Julie's conditions were itemized it was clear to me that it would be challenging to meet the standards. It would take some planning and patience. Given busy schedules and the out-of-town requirement this might take months. The good news was her process implied there might be multiple experiences. I countered with a proposal to skip first base suggesting that that was simply trivial and cruel - at least reward the guy with getting to second base I argued. She consented but made it clear she thought it would be very difficult to me et her conditions. "In the meantime, I'll continue to dress sexy and be a bit of an exhibitionist and you can continue to get aroused as a voyeur and fuck me silly after our dates." She giggled.

As it turned out it took four months and three attempts before we got anywhere close to having a chance for moving beyond some casual exhibitionist teasing. Julie had accompanied me on a business trip to Dallas. It was Friday evening. The meetings were over and Julie and I spent Friday afternoon shopping then headed to a restaurant in the West end. Julie looked hot in a new gauzy sundress. Soft blonde curls hung on her bare shoulders and her long tan legs and sexy sandals complemented her body hugging dress. Julie was in a great mood and doing her best to get the attention of the handsome young waiter.

He looked like a college jock who worked in the popular restaurant for spending money and a chance to meet young women. In spite of showing generous amounts of cleavage and leg and using every opportunity to make eye contact or otherwise flirt, she was having unusually bad luck. As we were eating fruit sorbet for dessert we noticed our waiter hugging the newly arrived male guest that was apparently his boyfriend. We were both laughing with the realization that Julie's efforts at flirting were in vain. As we laughed, a gentleman seated at an adjacent table walked over. He was also laughing then indicated that he had very much enjoyed watching Julie attempt to flirt with the waiter. He said he too was fooled and that she shouldn't feel bad as any heterosexual male would've certainly enjoyed her attention.

The gentleman was charming, slender and well groomed with graying sideburns, probably about 50. I invited him to sit with us as we finished our dessert and ordered coffee. He immediately focused all his attention and Julie and they were quickly chatting like old friends. He was extremely interesting and funny relating stories of travel and funny business experiences. It was soon clear that he was wealthy and quite a womanizer, he had mentioned at least two previous wives. It wasn't long before he inquired as to why Julie had been flirting with the waiter. Julie paused, looked at me, then smiled and said she sometimes just found it fun to flirt with someone else.

We visited another 20 minutes or so and then I mentioned it was time for us to catch a cab and head back to our hotel at the Galleria. Ben, ever the gentleman, volunteered to give us a ride back to our hotel.

We exited the restaurant and walked a block to the parking lot. Ben's car was a brand new 2002 Mercedes S55 AMG. I immediately complemented him on the car mentioning I had always wanted to drive one of those.

Julia interjected, "If you let my husband drive you can sit in the backseat with me."

Ben only hesitated momentarily before handing me the keys and opening the door for Julie. I knew the Dallas roads well and he briefly instructed me on where the car controls were. And we were off.

It was about a 10 mile ride to the hotel.As I waited in line to pay the parking attendant, Ben and Julia were visiting quietly in the back seat and I noticed Ben already had his hand on Julie's thigh. Julie giggled then leaned toward Ben and whispered in his ear. We hadn't gone a mile when I heard kissing in the backseat. As we drove under streetlights I attempted to catch glances in the rearview mirror. Hands were moving. Ben's head was nestled in Julie's neck and Julie was making sounds suggesting Ben's lips and tongue had found sensitive areas on her neck and shoulders.

Exiting the freeway less than 10 minutes later, the light from the well-lit local streets coming through the windows and moon roof revealed Ben sitting sideways in his seat with his left hand fondling Julie's right breast while they kissed lustfully. I was hard as a rock with my cock having pushed its way out of my briefs and laying fully engorged down my leg. My heart was beating rapidly and I was sweating slightly from excitement while trying to carefully navigate the hundred thousand dollar car while I snuck glances in the backseat.

We were only a few minutes from the hotel. At the next red light I turned to look in the backseat for the first time since leaving downtown. The left shoulder straps on Julie's dress was hanging down her arm and Ben's hand was now cupping and fondling her bare right breast having pushed the dress top down below her breast. I presumed his right hand had slid behind Julie to fondle her ass. Julie's head was laid-back and her eyes were closed. There was a smile on her face. Ben's head was nuzzled low in her cleavage.

I told Julie and Ben that we were one minute away from the hotel. Moments later I pulled into the entryway as Julie and Ben quickly broke their embrace and straightened up as of the Bellman approached to open the doors. Julie barely had her dress back in place as the door opened. Both Ben and I had some adjustments to make before we could exit the car without revealing tented slacks.

As we all exited the car I handed Ben the keys and thanked him for the opportunity to drive his beautiful car. Julie kissed him good night and thanked him for the fun time. I think Ben was somewhat surprised he wasn't invited up to the room. He graciously thanked Julie and me for the company and memories. He pulled me aside and whispered in my ear that my horny wife really needed to be fucked hard. He said if you ever need any help let me know and he discretely pressed some paper in my hand before climbing in his expensive hardware and heading out.

As soon as the elevator door closed and we were headed to our room I mimicked Ben's actions by lustfully kissing Julie while my left hand replaced his on her breast. Her still engorged nipples hardened further. Once in our room, Julie's dress was quickly shed and I proceeded to strip her of her soaked panties as I guided her to the bed. For the next two hours we went at it like lustful teenagers. I recounted my excitement in catching glances of Ben enjoying Julie's body and Julie filled in details of her 12 minute make out session. Julie recounted how Ben repeatedly attempted to "steal third base" by putting his hand up her skirt and in her panties but she finally distracted him by placing his hand on her breast instead. Julie was breathing hard just retelling the story and soaking wet and hot when I slipped into her and began slamming her into the mattress. She quickly erupted in her first orgasm. I had never seen her cum so quickly. We went at it two more times that night before collapsing for the night. It was now increasingly common for Julie to have multiple orgasms in an evening.

The next morning I woke up first. The room smelled of sex and our clothes were strewn across the room. As I picked things up I found the paper that Ben had handed me. It turned out to be his business card and a second card with a web address for a club called The Outer Limits. In light of our commitment to anonymity I stuck cards in my travel bag so Julie wouldn't see them. When Julie awoke I looked at her and smiled and said, "Fun night?"

I told her it was time to get packing as we had a drive ahead of us to get home to relieve the babysitter. As we began our 3 Hour drive I asked her how she felt about last night. She responded by asking me how I felt.

I told her, "I asked first."

She looked at me and said, "It was fun. The flirting was fun. Making out in the car was exciting. The hot sex when we got back to the room was great. And you?"

"You know I love to watch you flirt and get excited. I find it exciting when other men are interested in you. I was so excited and shaking so much when I was driving Ben's car that I thought I'd wrap it around a light pole. That's why I didn't watch any more beyond taking glances in the rearview mirror. I was afraid to take my eyes off the road." I said.

"It's a good thing that was only a 10 minute drive to the hotel." Julie admitted, "Any more time and I would not have been able to resist Ben's advances. I was getting excited when he kissed my neck and he had his right hand squeezing my butt." Julie continued. "When I put his hand on my chest he was content for a minute fondling me but quickly slid down my shoulder strap and grabbed my bare breast. - It felt exciting. He was a good kisser too."

I was getting excited again just hearing her talk about it. She asked me if I got jealous. I could honestly answer no. "Excited yes, jealous no - I have to admit I was a little jealous of his car though."

I asked Julie if she was ready for the next step. Then before she could respond I told her I thought we needed to skip "third base" it was simply not realistic to get verification that somebody was clean and get them excited with heavy petting but not expect them to want to fuck her. "That would just be cruel teasing." I said.

Julie thought about it a few moments and agreed noting that it took us four months to get to first and second base and even that didn't work like we planned so who knows how long or if we'll ever have things work out again. There was no question the burden was on me to find a way to have a fun, safe, anonymous, liaison with somebody that Julie found exciting.

Back in our normal routine we were very busy. I couple times a week I would find myself thinking about how to connect with someone to fuck Julie.

Julie had long since vetoed any Internet or magazine advertising. She simply didn't have confidence that we could screen out folks adequately. She also added another wrinkle to her requirements. If it was a married man his wife had to know he was fooling around. Our busy fall passed quickly and then we were in the midst of the holiday season. It had been almost 6 months with no progress. We had had a few fun outings where Julie flirted and flashed but no progress on taking the next step. While packing to visit the in-laws over Christmas, I refound the card Ben had left me in one of my travel bags. I decided to check it out on the web.

As it turns out, the club was a swinging and swapping club in Dallas Texas. From the website it looked real classy. The photos of the members, all with their faces blacked out suggested a classy attractive clientele. My interest was piqued when I noticed that membership was restricted to couples and unmarried singles and required health records, a credit check, and referrals from an existing member. I quickly realized those criteria mirrored Julie's requirements for an extramarital experience. The $100 application fee and $1500 couple membership fee were further assurance of a relatively select clientele. I quickly checked Ben's business card intending to e-mail him and see if he was a member and why he had given me the card.

It was three days later, after Christmas, before I was able to check e-mails. Ben had responded indicating he was a member and part owner. He sensed that we were exploring our sexual boundaries and thought we might be interested in the club. He was surprised he had not heard from us earlier. He indicated that we could be his guest for a visit and avoid the membership commitment but health records would be required. He said he hoped we'd follow through and looked forward to the prospect of someday seeing Julie again. He mentioned that Julie was the only women since high school that he had made out with without fucking.

I began considering how to broach the subject with Julie. Dallas was a three-hour drive and a frequent destination of mine for business trips. The 170 mile distance was a nice buffer between a household with two 13-year-olds and in-laws and friends in town and the excitement of sexual experimentation in the big city. I searched our files to find the necessary medical information from recent annual physicals and began thinking more about the possibility. This was a real different scenario than Julie and I had talked about. We hadn't talked about me being with other women, Julie having to compete for the attention of men with other women, and the prospect of multiple men at the same time.

It took me a few weeks to discretely dig up the health records before I completed and faxed Ben the materials. I decided to not broach the subject with Julie yet. In late January I received positive confirmation from Ben. A note encouraged us to plan to attend the annual Valentine's Day party scheduled for Saturday the 15th. The next evening I invited Julie for a Valentines weekend in Dallas. I asked my folks to babysit. She was excited as she enjoyed trying new restaurants and shopping in the city. I didn't reveal my plan but she suspected something. It was an anxious three week wait.

The following Sunday morning Julie shook me to wake me up and with a worried tone asked if I was OK. I was sweating, had been mumbling something, breathing hard, and, as I soon realized, had a huge erection. I told her I was fine but had been dreaming.

She laughed at me saying it must have been quite a dream. She pulled the sheets off my lower body and threw her leg over my torso then hiked up her long pajama shirt and positioned herself. She slowly lowered her body directing my cock into her pussy as she slowly lowered herself. When she was fully stuffed she smiled and said, "Frank sure is big this morning, why don't you tell me about your dream?"

I told her I couldn't remember the details but when she woke me I was watching her on a bed in the middle of a room. As I slowly began thrusting into her and palmed her breasts under her nightshirt, I continued. "Your skirt and blouse were in a pile on the floor and you were wearing a sexy black bra, panties, garter belt and stockings; kneeling on all fours in the middle of the bed. A handsome man was kneeling in front of you with his one hand on your head and fingers entwined in your hair, the other hand on your shoulder. His cock was three-quarter of the way down your throat. There was another man, equally handsome, behind you and between your legs. He must have been in a hurry, as he just pulled the panty fabric to the side and slid his cock in from behind. He slid right in to the hilt.

You must have been hot, wet, and ready. You were being rocked back and forth, stuffed from both ends. The man in front reached around you and pulled the bra cup down so your tit spilled out. He was fondling your sensitive aroused nipple. Your body was quivering and you were moaning as much as you could with a mouth full of cock - then you woke me up."

Julie didn't say anything. I kept thrusting and Julie was now rocking aggressively on my cock. She looked slightly flushed and was breathing deeply as she yanked off her pajama top and ground her ass on my groin. My hands were full of tits. In a few moments we both climaxed.

I knew Julie was ready for the next step.

My plan was to drive to Dallas Friday afternoon, check in the hotel and go to dinner. Then Saturday go shopping, relax over a light dinner and then go to the party. Julie still didn't know about the party but knew I had romance planned as we had restrained from sex all week. I could tell Julie was nervous as was I on the three-hour trip to Dallas. She looked fantastic.

While shopping I bought Julie a charcoal colored, shiny semi sheer blouse that would look great with the valentine's gift outfit that I had in my luggage.

I had Julie open it as she prepared to dress for dinner. It consisted of a black sheer bra, panty, garter and stocking set and a black leather slit skirt just long enough to hide the garter straps and stocking tops if she was standing. She looked delicious. We had a delightful light diner and a few cocktails. I told Julie I had a special surprise for her - that we had been invited to a party. I told her that if she was uncomfortable at any time we could leave but that I hoped she wouldn't prejudge anything and give it a try.

We drove the 20 mile hike north of town. As we approached I handed Julie a scarf and asked her to blindfold herself. She giggled a little nervous giggle then complied. I pulled in and parked. The facility looked like the country club at a golf course. I was guessing it was 15,000 ft.² - the size of a serious mansion. There were perhaps 30 cars parked in the lot. It was about 10 o'clock. I helped Julie from the car and guided her up the front walk in her blindfold.

I knocked and was promptly greeted by a gentleman who looked at me briefly then addressed Julie and I by our first names. He welcomed us and said he would escort us to our room. We walked through the lobby like room down a long hallway. I could hear music and at one point could see large windows overlooking the pool and patio area in the backyard where many folks were gathered. He opened the door to a good-sized room and ushered us in. He told us there were champagne, crackers and cheese; chocolate dipped strawberries, and assorted other goodies. He then said, "After your initiation is complete in an hour or so feel free to join us in the pool and hot tub area out back. He then excused himself and left.