Roman Holiday

Roland commented on the agony of being caged, something he had voluntarily committed to doing. He could have said no or not told me, but he volunteered the information even telling me about the key and tiny padlock. Until he told me I had no idea chastity cages existed.

"Just a few more days, Roland, and you'll be home and your little penis free, but only after I've had enough of your face between my legs."

He sounded very frustrated, "It's going to be more than a few days. My boss called today. The asshole wants me to stay another two weeks."

Asshole is right I thought. I wanted Roland home now, not two more weeks.

I know I sounded disappointed and I didn't care, "Asshole is right. I'm bummed and you're bummed, but look on the bright side."

"There's a bright side?" he asked.

I had been thinking of confessing everything, the two handed handjob I gave to a dying Jan, the makeout session with Ricky while Roland was passed out in the front seat, my almost affair with Ricky, and Mr. Married Man fucking me in our marital bed, but what I had in mind was infinitely better.

"Hmm hmm, there is."

He wasn't seeing the upside, just two more weeks of blue balls and not getting to eat me.

"In two weeks I can be having an affair with that asshole boss of yours. What's his name?"

I asked knowing his name.

"Not him," he protested, "Anybody but Richard. He already makes my life hell."

"Does he now? Too bad. Your life is about to get tougher."

"Jeanette, please. Not Richard. He'll be even more insufferable than he already is."

"I know. That's why he's perfect. Besides, I've already made up mind. The matter is closed for discussion. Richard, it is."

Dead silence followed. He didn't continue to plead his case. I wondered if I had pushed too hard or was he quiet because he was having one of those cuckold moments he and his friends wrote about. The boss fucking his wife was hugely humiliating and hugely arousing.

I even thought he might be speechless because he was trying to articulate why it wasn't a good idea. Honestly, it was a horrible idea which is why it was perfect.

Since he wasn't talking I decided I would, "Roland, isn't Dick a nickname for Richard?"

"Huh huh," not seeing where I was going with my question.

"Then it's even more perfect. Your wife will be getting dicked by Dick, the biggest dick you have ever worked for."

I got him to laugh because even he had to admit it was damn funny. Dick dicking me.

I laughed too. After we were through laughing about my play on words we both got quiet. I really had nothing else to say. I had made up my mind. Roland's protest was pretty lame, but if I had any doubts as to whether he was in or out, his next comment cleared them up.

He broke the silence, "What about protection? Are you going to insist he wear a condom?"

I could hear the excitement in his voice. He was on board.

"No, Roland, I wasn't planning to. If he gets me pregnant, you'll have to deal with it."

His voice got really deep. He was definitely aroused, "I'll deal with it. You are going to be even sexier pregnant."

"Turned on?" I asked.

"Very."

"Then it's a good thing you're wearing that cage. I want your focus on what I'm doing. By the way did you mail me the key?"

"I did," he answered.

We talked some about mundane things, but he was obviously distracted.

"Roland, are you imagining Richard fucking me?"

"I am. You're pregnant. On your hands and knees. Your belly is huge as are your tits. He is fucking you doggy style."

"That's a very nice picture you drew Roland. I just touched myself. I am soaking. I might have to masturbate later. I had better go. I have a busy day tomorrow thinking about how I'm going to seduce Richard."

I fell asleep, but not before masturbating using my big, black dildo I had named Jan.

As I fucked myself with Jan I fantasized about Roland's boss, Richard, fucking me. Not only did he fuck me, but in my fantasy he impregnated me while Roland watched and masturbated. As Richard filled me with his seed, Roland's penis erupted shooting stream after stream into the air where it fell on the floor instead of where it belonged, inside of my vagina, making nothing but a mess he would have to clean up when it should have been making a baby with me, his wife.

Afterwards I fell into a deep and very contented sleep. I awoke feeling rested and full of energy. Toweling off in front of the bathroom mirror I pictured myself as Roland pictured me, belly heavy with child and breasts swollen with milk. I couldn't wait to get pregnant.

All I had to do was seduce Richard; Darwin and natural selection would take care of the rest.

Seducing Richard turned out to be pretty easy. I purposely involved Roland because he provided me the perfect cover story for why I was visiting the office and because it felt good to hear his reaction as I twisted my adulterous, slutty, and shameless knife. I didn't feel guilty because he had made it quite clear in both his writings and his actions he wanted to be betrayed, humiliated, and denied.

I began my seduction by insisting Roland call Richard to let him know I would be coming to the office to pick up some papers he had forgotten, papers he now needed me to Fed Ex to him.

I detected discomfort, but also arousal in Roland's voice when I told him what he needed to do. He asked if he had to and wondered why I couldn't just show up. I answered him with a question. How badly did he want another man to fuck me?

As I suspected his whining was just an act, part of the persona he was playing, only it wasn't pretend.

He was breathing faster, a sure sign of arousal, "I'll do it. I do have some things from the office I could use here."

I cut the call short telling him to call me after he had spoken with Richard.

I went to bed, but not before fucking myself while fantasizing about being with Richard.

I really didn't know Richard. He was several decades older than Roland and I. He was a big man, at least 6 feet 6 inches, barrel chested, round face, tanned from lots of golf, athletic, but he had a gut, was chauvinistic, opinionated, a bit of a bully, and used to intimidating people with his size and position. He demanded obedience from his subordinates. He made his bosses a lot of money.

I imagined Richard's dominance in the work enviornment would carry over into the bedroom. I had several toe curling orgasms imagining Richard putting me through the paces making me prove I was worthy not just for his cock, but to carry his child.

The next night Roland called to tell me he had spoken with Richard and he would be on the lookout for me. I asked Roland what I was picking up or would the papers be waiting for me all neatly arranged on Richard's desk.

Roland answered, "No. You wouldn't have any reason to be there for more than a minute. You'll have to find and assemble them. Once you've got them all together I think you should show them to Richard and get his approval before sending them to me."

I told Roland, "I like your plan. You've obviously put some thought into this. Tell me. What kind of man is Richard, tits, ass, or leg? I need to know how to dress."

My calm both excited and unnerved Roland.

He actually stuttered, "I d-d-d-on't k-k-know."

"I thought he was your boss. Surely you've objectified and talked about women, your likes, dislikes, his likes dislikes."

"We have. He's more of an ass and tits man, but he likes legs too."

His voice grew soft, barely above a whisper, "He told me he wouldn't mind tapping you, said you were the complete package, told me he envied what I was tapping."

I felt equal parts arousal and anger. Mad my own husband saw me as nothing more than an object for he and others to use sexually. They didn't care about me emotionally or see beyond my physical attributes. I was a piece of meat.

At the same time there was something very appealing about being desired on such a primitive level. No strings attached sex. Thankfully, men like Richard and Mr. Married Man had big egos driving them to sexually satisfy their women. Making a woman orgasm wasn't done for the sake of the woman, but to validate the man's prowess.

I both hated and wanted Richard. I couldn't wait for his big cock to fill me up. As for how I felt about Roland, conflicted. Was he pushing me to have sex with other men because he cared about my pleasure or his own?

I ignored Roland's comments and changed subjects talking about our respective work days. We talked about the house, the weather, and my cooking. I told him I missed him and I asked him if he missed me.

He said he did. He then choked up. He did something I had never heard him do. He started to cry. He apologized for all the lies, his sexual fantasies, and his feelings of inadequacy, for not just having them, but for not having shared them with me, his wife. He said he had been a lousy friend.

I felt bad for him because everything he said was true. He had been a lousy friend, husband, and lover. He had been deceiving me for a very long time. After sex with Mr. Married Man and masturbating with the dildo he bought me I concluded all the lies were built on a truth. He was sexually inadequate and now we both knew it.

My voice he said had never sounded sweeter.

"Roland, honey, I accept your apology. Quit beating yourself up. I'm not going to leave you. I love you very much. I will support you on this, but no more lies. You built a wall between us, but we're knocking it down. Now, let's talk about Richard and how he and I are going to make a baby. Tell me how you imagine this plays out."

I quickly learned he had given it a lot of thought. He was both very scared and aroused and very obsessed. I took Jan and slowly fucked myself as he described how my affair with Richard would play out. I was totally turned on and told him so. Jan felt good, but what I really craved was Roland's mouth on my pussy. When Roland returned I was going to demand lots of oral.

He imagined Richard fucking me on our bed. He wanted me to call him and leave the phone off the hook while it happened. He wanted me to become emotionally attached to Richard, to be his girlfriend, to go on dates, to come back home and tell him about my dates as he worshiped me with his tongue.

I encouraged him to keep talking as my orgasm was building.

"Roland, tell me how you imagine Richard and I making a baby."

What he told me pushed me over the edge. I put the phone down, used both hands and rapidly fucked myself as my orgasm washed over me.

I needed a minute to catch my breath and gather my thoughts. My body was on fire.

I picked up the phone.

He said, "That sounded intense."

I assured him, "It was."

Regarding his fantasy, "That was hot Roland. We can make it happen, but first we need to get Richard and I together. Let's talk about tomorrow."