Chapter 1: In Which The Bachelor Party follows the Wedding Night

Emily

For seven years, I made more trips to Pittsburgh than I had actual business in that city. The reason was simple: I got infatuated with a woman. More accurately, I fell for a call girl who ran her own outcall service. Despite what people say, it does happen. Despite what people say, it's not always a disaster and I have no regrets about proposing to Tabby twice before her retirement. It didn't end badly for either of us, despite what people say.

My last few trips to Pittsburgh, Tabby had arranged for me to meet with one of her associates instead of her. On each occasion, my time with Tabby had been limited to a quick hug in the hotel lobby and ten minutes of conversation. As always, Tabby's treasures never disappointed except for the fact that no one ever measured up to the boss. I accepted the situation, Tabby was retiring and wasn't doing appointments herself anymore. This time though, she suggested that we have dinner before she introduced me to dessert.

I'd prepared myself for a pleasant dinner before Tabby handed me over to some extremely attractive and sexually-skilled but, to me, interchangeable young woman. For six months, I'd been mostly paying for the opportunity to chat with Tabby in the lobby.

She was already at the table when I got to the restaurant. At our previous handoff meetings, Tabby had dressed business casual so she wouldn't upstage my date. This time, she wore a black dress that showed off the tops of her breasts and a hint of a lace bra. A cutout revealed the girlish flatness of her tummy and she had on heels that made her rear roll as if ready to rock. When she pulled me to her for a quick hug and what turned out to be a lingering kiss, my cock responded immediately.

"I see you brought your friend along for dinner," she whispered then ran her tongue along the edge of my ear.

"Well, he was quite insistent about coming."

"Is that a promise, Jerry?"

By the time we sat down, I was thoroughly confused, but also had the feeling that was exactly what Tabby wanted. We clinked glasses.

"May the loveliest woman I know be as happy in retirement as she's made me."

"Well, I haven't retired quite yet." She winked.

"Did you break up with your boyfriend?"

"Charley and Alix are fine. They're in California."

"I knew about Charley, but who's this guy Alex?"

"She's my girlfriend."

"I thought Charley was your boyfriend."

"She's his girlfriend too. Very cute blonde, tight-petite body. If you remember Darcy?"

It took me a second, but I blushed as I remembered the lady who was probably the only one of Tabby's associates who rivalled the boss, "Oh, wow!"

"I like to think that I'm the lucky one."

"If Alix is anything like you or Darcy, this Charley guy must have his hands full."

"Actually, it's the other way around. There are nights when he's a bit much for the two of us. Thankfully, I have a little experience finding ladies for horny gentlemen."

"Tabby, I don't get it. You're more than enough for any man. Why would you settle for less than all of a his attention and love?"

"Jerry, you remember my telling you that you didn't really know me when you proposed?"

"Of couse, you said that both times."

"You might the sweetest men I've ever met. It's obvious that your idea of happiness is to find a woman and envelope her in your love."

"Naturally."

"That would make me claustrophobic."

"You don't have to be that way Tabby. It's just a matter of trusting. If I'm not the right guy, I'm sure..."

"I'm not sure you get it, Jerry."

"I just don't get why a woman like you would settle for less. I don't care how handsome, charming, or rich this Charley is. You shouldn't have to share him. You deserve the whole package."

Tabby shook her head. I had a feeling she was starting to get annoyed.

"Charley's older than you. He's not as good looking as you. I have more money than Charley. He's a regular guy in many ways."

"I guess I thought that if you'd settle in with a man that he'd be as incredible as you."

"I think when you've been with as many men as I have, different things matter. It's not that I don't look at men, it's more that what turns me on might not be as obvious."

"Does he have a nine inch cock or something?"

Tabby laughed, "Guys are so weird. It always comes down to that. If it makes you feel better, you're at least an inch longer and much thicker. I've always loved the way you fill up my pussy and how it's a struggle to get all of you in my throat."

"That's not part of the show?"

"Jerry, I told you a long time ago that I've never had to act when I'm with you. I'm not that big a girl, so you're right on the edge for me.You're a terrific lover and total boyfriend material."

"Boyfriend material," was code for a client a working girl would consider dating.

She kissed me. Her hand brushed my thigh. I reached for her face and touched her thick dark hair.

"Why don't you pay the check, Jerry? It's time for dessert."

Despite her fuck-me outfit and the flirting, I still assumed that Tabby would hand me over to her associate who usually turned out to be the cutest woman other than Tabby at the bar. When Tabby got back to our table, I was fully expecting this to be the end of our evening and our friendship. She touched my cheek and squeezed my shoulder."So, I want to make sure I have this right. Most men's ultimate sexual fantasy is to be with two women or to do some sort of role play where they do wild things to all of my orifices. But, that's not for you?"

I nodded.

"Your fantasy is to be alone with a woman you love."

"And who loves me back."

"Would you settle for a night with a thirty-four year old single mom who runs an escort service instead?"

I took her hand.

"Tabby, for the last five years, you've been my fantasy. You're the only woman I want to be with, even if it's just one more night."

"Jerry, I want you to understand something. I didn't say no because I didn't think I could love you. It's more that I can't give you what you really want. I can't handle the responsibility of being the only love of someone's life for an entire life. I've really been flattered that you want to share something so precious with me."

"Tabby, I know what you're saying. It's time for me to move on and meet the right girl."

She shook her head. Her brown eyes stared straight into my soul."I wasn't finished Jerry. I was hoping you'd give me a wedding gift?"

"Sure, I guess I'm surprised you'd ask, but I guess I won't be seeing you after tonight and I do think of you as one of my most intimate friends. Are you registered somewhere?"

Visions of blenders and china settings flitted through my mind.

"As a matter of fact, I registered just before dinner."

I pulled out my cell phone to write it down.

"Where?"

"The honeymoon suite at the Regency."

I looked at her quizzically.

"I didn't realize that Charley and Alix were in Pittsburgh with you."

"Actually, they're in Minneapolis right now.

"Are you asking me to pay for a night at the Regency as your wedding gift?"

"I guess I am."

She winked at me flirtatiously.

"Shouldn't Charley be paying for your honeymoon suite?"

"Why should he pay if he's not going to be there."

I didn't get it at first. As soon as I did, my heart jumped and my cock stirred.

"I hope you don't mind living out your fantasy with the wrong girl." She winked flirtatiously, but that quickly gave way to a completely different vibe. Most of the time, Tabby was bubbly in my company. There was a vulnerability in her face that she'd never before revealed. She put her hand palm up on the table.

"So, there's no associate of yours who's joining us for dessert?"

"Jerry, for a really smart guy, you can be pretty slow sometimes."

"Does this mean that you've changed your mind about my proposals?"

"Jerry, before you get the wrong idea, I'm still marrying Charley and Alix."

"Then what are we talking about here?"

She ran her tongue across her upper lip then squeezed my hand.

"Well, I can't give you a lifetime together, but was wondering if you would give me a wedding night?"

"You mean?"

"The two of us free to express our love for one another in any way we see fit. We'll be one man, one woman, who happen to be in love sharing one room for one night. I won't get to have that kind of wedding night in my marriage."

"Tabby, I have to confess that's exactly what I've done with you whenever we've been together."

Sadness crossed her face. Tabby took both my hands in hers.

"Jerry, I need to confess too. I've given you sexual pleasure and certainly genuine affection and friendship, but I've never given you love."

I could only sigh. I had convinced myself that she had.

"I'm worried that if I share this side of me, it'll be even harder for you in the long run. My asking you for this gift might not be fair. I know that sounds a little conceited, but you're not the only man who's gotten addicted to my company. You are the only one I want to do this for."

Someone must have turned up the thermostat, because my insides were melting. It took some effort for me to speak clearly.

"Tabby, I'm a grown up. I know that I've been paying you to be with me. I also know that it's really going to hurt maybe for a long time to wake up in the morning and know what happened the night before can't ever happen again. At the same time, there's no amount of pain or sadness that I wouldn't risk to make love with you just once."

"If you just want to fuck me, that's fine too." She giggled.

Tabby pulled my face to hers and kissed me. I'd exchanged thousands of kisses with her on our dates, but this was clearly different. Before this, I was convinced that Tabby kissed me more passionately than any real girlfriend that I'd ever had. That included my ex-wife when we were head over heels in love and still twenty. This kiss didn't just reached inside me it had hooks in it. This wasn't Tabby the sexual magician, it was Tabby the woman behind the magician and the girl inside the woman. I didn't want to pull away, ever. It was so intense, that I began to wonder if I really could get over losing whatever was going to happen between us. Once that thought crossed my mind, I didn't want to pull away, but I did.

"Is everything okay, Jerry?

"I forgot to pack my Viagra."

"Believe me, what you're packing will be just fine."

Tabby kissed me again, but lightly. I gave the cab driver fifty bucks to break the sound barrier.

A part of me says that I shouldn't share what happened that night, but I need to. Even now, I might still be replaying it in my mind. This sounds corny, but my mother gave my wedding ring to give to my first wife. When we broke up, my ex gave it back and told me that she hoped that I found the woman who would do better by me. I was touched, because Jodie had a very good relationship with my mom when mom was still alive. My first reaction was to say that we'd save the ring for our daughter, Cheryl. Jodie told me that I needed to find the woman who deserved my mother's ring, before I passed it on to Cheryl.

As cheating bitches went, Jodie was a better ex-wife than wife and we always stayed friends. That doesn't happen often after you walk in on your wife with two of your best friends, at the same time no less. I knew it meant nothing and that Jodie simply loved sex, but I finally realized that I needed to be with a one-man woman and Jodie wasn't even a one-man-at-a-time woman. I probably should have gotten a clue that first time we had sex and she put a condom on me without using her hands. Looking back, I'm not completely sure how Jodie paid for college. I lost the friends, but kept Jodie as a best friend somehow.

Obviously, it doesn't make a lot of sense for a one-woman man to fall in love with a call girl. Jodie told me I needed to try "good girls" if I wanted to be happy. She even tried to set me up with some, but they were Jodie's friends and it turned out there were things about them that Jodie didn't know. My biggest problem romantically is that I have a thing for bad girls. My weird fantasy is that my Ms. Right will love me so much that she'll decide that she only wants to be wild and bad with me.

After Jodie, I'd kept mom's ring on a chain around my neck as a reminder of what I really wanted in the end. I usually took it off when seeing escorts, butI'd worn it during all my "dates" with Tabby. When Tabby and I got to the door of the honeymoon suite, I went to one knee. She was horrified at first. "Jerry, I told you that this is one night only."

"Tabby, if we're going to do this right, I have to propose properly. If this night's going to be a wedding night, you're going to have to wear it this time."

She started to cry. "Jerry, I was worried that you might have a little trouble separating after tonight. Now, I'm starting to worry more that you might change my mind and I'll be the one who's not going to be able to give this up."

I took her hand.

"Tabby, this was my mother's wedding ring. She wouldn't take it off even after my father died. She gave it to me to give to the woman I wanted to spend the rest of my life with. I just wish you could keep it for more than a night, but my memories of you and this night will spent the rest of my life with me."

Her finger shook as I slipped it on or was that my hand doing the trembling?

"I love you Tabby. Some part of me always will."

"I love being your wife, Jerry."

We locked into another passionate kiss. Somewhere in there I had the presence of mind to slide the card, open the door, and nudge our intertwined bodies into the honeymoon suite. For fifteen minutes, neither of us had any idea what the room looked like. If there were ever a moment when I wanted time to come to a complete stop, this was it.

Tabby broke away for a moment. "I think it's time to get a little more comfortable."

She pointed me in the direction of one of those white-fluffy robes, then disappeared to the bathroom. The room's fireplace was already going. The curtains were open to a twentieth- story view of the skyline. A bottle of champagne on ice and a bowl of luscious-red-sliced strawberries sat atop a table next to a turned-down king bed. A can of low fat whipped cream sat next to the strawberries. As I pictured uses for the whipped cream, my erection pushed out the front of my robe.

"Is that for me?"

I hurriedly pulled the robe over my exposed penis, something I'd never worried about before in Tabby's presence.

I looked up to see the most beautiful woman I'd ever laid eyes on. Tabby had put her hair up giving me a full view of her gorgeous face. She wore a virginally modest-white peignoir that went to the floor. I could see through the material, but couldn't quite see Tabby's bare skin or even what she might have on underneath. She balanced on a pair of red heels.

I fluttered my hand over my heart.

"You're so gorgeous."

"I wanted to make sure that I looked just right for my first time with my husband."

"Can I just look at you for a couple minutes? I don't want to ever forget this."

She blushed.

"You will be gentle with me?"

"I might be a little too turned on to be gentle, but I can promise tender."

We kissed some more then sat down to toast our wedding night, each sipping from the other's champagne flute.

"Jerry, I love that fire, but it's a little warm in here. Do you think you could help me get this off?"

"I thought you'd never ask."

Tabby turned her back to me, making sure to brush the fabric of her nightgown against the bare skin of my arms. I untied the row of delicate lace knots that held the peignoir in place like a present, then watched it drop around Tabby's ankles. She wrapped her arms around herself like a girl who had never been alone with a man before.

"I didn't know you were ever shy about my seeing your body?"

"Jerry, I've never been this naked with you."

"Let me look at you some more?"

"Only if I can look at you first."

She helped me slip off my robe. My penis stood at a right angle from my body. I don't know that it's ever looked bigger.

"Jerry, you've got a beautiful body. I love how you're in shape, but clearly not the kind of guy who lifts just to look good. You're just so manly. I got pretty excited that first time we were together."

My cock twitched from three o'clock to one-thirty.

"I guess I never knew that."

"Well, there were a lot of times I wanted to stay longer."

"But you've always been generous about time."

"I mean like a couple months. I really meant what I said about my feelings for you."

"Oh."

She touched my cock shaft with her fingertips.Tabby stepped away from the nightgown and offered a second toast.

"I hope this memory lasts us both a lifetime."

"I'll drink to that."

She twirled around for me and posed. She had on a pair of black stockings and garters, a sheer G-string accented her perfect ass and flat stomach. A black pushup bra covered breasts that looked as if they came out of some 36 C mold for the ideal balance between fullness, form, and uplift.

"I hope you want to do more than just look."

"If I look any longer, I'm not going to be able to guarantee that I'll be gentle."

Tabby giggled.

"You know Jerry, when you stare like that, it gets me really wet."

She reached for my hand and led me to the bed. She started to take off her heels, but I insisted they stay on. With our heads next to each other on the pillow, we kissed yet again as our hands explored one another's torsos.

"I want you inside me, Jerry!" she whispered.

"I want to be inside you my love."

"Jerry, don't worry about me. I'm ready."

"But I have to unwrap you first."

I kissed her then crawled to the foot of the bed where I slipped off the red high heels one at a time and began to massage her feet and toes as I let the dream begin.

"Even your big toe is gorgeous, darling."

They wiggled involuntarily as I unpinned her stockings and rolled them down slowly. For the next half hour I kissed, licked, and massaged every bit of Tabby's exquisitely proportioned lower body. She cooed her approval.

"I love the way you touch me. You're strong enough to be truly gentle. I feel so safe with you, honey."

"I'll always be there for you Tabby in every way."

I'd worked up to her inner thighs.

"Jerry dear, I want to return the favor."

"I don't think I'll have the patience to make it through one of your incredible massages Tabby."

"Who said anything about massaging you?"

She licked her lips and blew a kiss in my direction. I untied the knot on the side of her g-string then moved my face up to her pussy where Tabby's wonderfully female scent greeted me. I gave her a few exploratory licks and Tabby's cooing turned into moaning as my tongue found her clit. My finger slipped between the lips of her vagina. Before she could climax, I started to kiss my way up towards her belly button. She moaned, "You fucking tease."

"Don't worry sweetheart, I'll be back, I promise. I just want to touch every bit of you first."

When I unhooked Tabby's bra to expose her breasts and nipples, I whispered, "I worship every inch of your body, but these are the temple."

I licked, kissed, and caressed them until her nipples swelled and her chest heaved with pleasure and anticipation. She was now fully naked.

"I love you more than you can imagine, Tabby."

"I love you too, Jerry, and I want it to be my turn."

"Not yet!"

I spent several more minutes playing with her breasts until her nipples seemed ready to explode. I kissed my way up until I gently massaged her scalp. We made out again, our tongues intertwined. It was as if we were trying to inhale one another.

Tabby rolled me onto my back and slowly kissed her way down my chest. By the time she reached my navel, the tip of my cock hit her cheek.

"Jerry, honey, did your cock grow since we were together last? I don't remember that happening before."

It hadn't, but it definitely did make contact at least an inch higher on my stomach than previous times when Tabby had kissed and licked her way down as a prelude to an exquisite blow job, the centerpiece of our sessions together. She cupped my balls in her right hand and ran her left index finger along the shaft.

"Jerry, I swear I'm not dreaming this. It's bigger and believe me I know something about cocks. You're huge."

It definitely did look bigger to me too and I was certain that whatever excess blood was in me had found its way there. It was redder than I'd ever seen it. This wasn't a boner, this was a steel girder.

"Do you think I can still get my mouth around you?"

She winked at me.

"I don't want to have premature ejaculation problems on my wedding night, but I'd love to watch you try."

She kissed the tip of my penis and my cock twitched its approval. My hips thrust in the direction of her face.

"Easy there boy. You know you don't come until Tabby lets you come."

Tabby made little circles with her fingertip along the bottom of my cockshaft.

"That feels wonderful, Tabby."

"I haven't even started on wonderful yet, Jerry."

Her tongue slithered along the underside of my shaft as her mouth covered my cock. I groaned.

"Jerry, you barely fit in my mouth. I don't know if I'm going to be able to deep throat you this time."