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Chapter 3 Terri
“Terri Gilmore, I’m Office Simon Westbrook investigating the death of Cynthia Rose. I understand you reported the crime. I have a few questions,” I shouted through the still closed apartment door. I was in an older remodeled home in Hyde Park. It was built as a single family home back when families were larger and the relatives lived together until they passed on. It was from an age where being a family member meant more than today.
“Show me your badge,” said a husky female voice.
I held it up to the peephole. Almost immediately, the door opened to reveal a tall black female dressed for the gym. She was quite an eyeful. Black spandex shorts covered two long shapely legs. Her bare mid riff revealed a concave abdomen whose musculature hinted of a six pack. Two large breasts were attempting to climb out the top of a jog bra. And the face wasn’t bad either. Stupid rednecks are put off by the Negroid lips of Afro-American women but I know how it feels to have those full lips racing up and down the length of my cock.
Terri had a firm handshake and plenty of muscle. I’m a gym freak myself and attracted to females with a BMI of less than twenty five. Hang around a health club long enough and it changes your idea of feminine beauty.
I had a fleeting thought I’d met her before. Then I reminded myself that if I’d met someone who looked as good as Terri, I’d remember her.
“I just got back from the club and need a shower. Can we talk as I clean up?” asked Terri.
“Sure,” I said. “Cleanliness is next to godliness, or so my Mom used to say.”
“Your Mom was right,” said Terri leading me into a bedroom decorated in pink and white. The carpet was white shag and out of respect, I kicked off my loafers before I entered.
“Thanks, that’s sweet,” said Terri slipping out of her bra. The boobs were undoubtedly augments but very nice augments with a large mahogany areola and quarter sized nipples that reminded me of the ripe blackberries we used to pick on my uncle’s farm.
“You called it in on your cell phone,” I asked as Terri went into the bathroom. She left the door partially open so I could see her backside as she slipped the spandex shorts down her thighs then stepped into the shower.
I had no idea why Terri was showing me her boobs and tushie. Maybe she was a cock teaser. Or she had a thing for cops. There are females, God bless them, who get turned on just looking at a blue uniform. But I was dressed in a suit and tie. I reminded myself I was a professional with a job to do and looked away from the door as Terri adjusted the water temperature.
“Never leave home without it. A girl jogging alone in the park can’t be too careful,” said Terri.
“Did you see any strangers in the park?”
“None, it’s pretty quiet in the Arboretum on Sunday morning,” said Terri.
“Have you ever witnessed any problems there before,” I asked?
“No, the reason I run there is that it’s safe. There are places in the city where guys think they have the right to grab your boobs as you run by,” said Terri.
“Tell me what you found,” I said.
“I was running at my normal eight minute mile pace along the shoulder of the road when I just happened to look down and see the fender of a car. That’s when I noticed the guard rail was banged up. I stopped and leaned over for a closer look. That’s when I saw that poor girl,” said Terri.
“Did you climb down to the wreck,” I asked?
“Yes, but just to see if she was alive. Of course, she wasn’t. I hope they find the pervert who stuck those speculums in her. That’s sick,” said Terri.
I heard the shower turn off and resisted the urge to watch as Terri exited the stall. “Yes, it was sick and unusual. Have you heard any rumors about weirdoes in the Arboretum?” Maybe someone in your health club mentioned something?”
“No, it looked to me like some nutcase found her body before me and tied her up. Then he fucked the poor dead thing and left her. I just hope her parents don’t see her like that. She was a pretty girl, damn shame,” said Terri arriving back in the bedroom wearing a towel. She took a seat at a dressing table and proceeded to blow dry her hair.
“The speculums part is unusual. You ever hear of anyone who likes to use them during or after a rape?” I asked.
I watched as Terri thought for a moment before answering. “No, not during a rape, but some guys want to see inside your love tunnel. I had a friend who used one to look up my bottom. Crazy bastard took a digital photo of the inside and made it the screen saver on his PC. He worked in Customer Service over at Commonwealth Pier for Fidelity.”
“You still in a relationship with him?” I asked.
“No, he was a little too weird for me,” said Terri.
“Anything else,” I asked?
“The S&M crowd is into speculums,” said Terri. “But what aren’t they into when you think about it.”
“How so,” I asked?
“I’ve seen one used to torture a vagina. The Master opens a slave girl’s pussy with a speculum then sticks a violet wand deep inside and pushes the button. He shocks the inside of her pussy. Sometimes he does her asshole too. It lights a girl up like a Christmas tree. If you like to hear someone scream, it’s one way to go,” said Terri demonstrating her knowledge of uncommon sexual practices.
This was turning out to be an interesting conversation. “Any idea where that kind of action goes down,” I asked.
“Club Macabre, for one” said Terri.
“Never heard of it, where is it located?”
“It moves around, no one place in particular, they rent out an abandoned warehouse for the weekend and email the members the location at the last minute,” said Terri.
Terri was turning out to a valuable source on Boston’s demimonde. “Like a rave, ever been to a meeting of Club Macabre?” I asked.
“Once, but sado-masochism is not my thing. Those people are insane. Guys getting their balls flattened and girls with needles in their boobs and blood everywhere. These babies cost too much to let some jerk puncture them and let the filling leak out,” said Terri. As she spoke she turned toward me and let the towel slip down.
“They’ve very beautiful,” I said and I meant every word of it.
She cupped her boobs and held them up for me to appreciate. My guess was thirty six C or D. “Officer Westbrook, I suppose I shouldn’t be surprised you don’t recognize me.”
It was time to be charming. After all she was showing me her tits. “Somehow you seem familiar but if I had met anyone was gorgeous as you I would have remembered her.”
“Simon, you always was a smoothie. Charmed me right out of my panties the first time we met. That was ten years ago. You were in uniform then. I took one look at you, all ramrod straight with every crease in place and decided I had to have some,” said Terri.
“Sorry, give me a clue,” I said.
Terri dropped the towel and my mouth dropped open. When she spread her legs, I recognized the eleven inch cock and the name of the owner came to me. “Terrence Bouclé.”
I was a rookie driving home after second shift when I happened to look into an alley and spotted three white guys beating the shit out of a tall skinny black boy. I was idealistic in those days and thought I could make a difference in Boston’s touchy race relations. I was out of my car in half a second racing down the ally to slam my nightstick on the head of a fat Irish goon. The three were drunk and to be honest, the black kid was giving a good account of himself even if he was outnumbered. It wasn’t long before the micks were lying on the pavement with busted heads.
“You’re under arrest,” I said reaching for my cuffs. I fully intended to take them back to Precinct D and throw them in jail.
“No, I don’t want to file a complaint,” said the black kid.
“Why not? It’s a hate crime and that moves it up the felony ladder,” I said. The three could get a year inside if convicted of a hate crime.
“Waste of your time, Officer. I’m a male prostitute. The judge will let them go with his blessing,” said Terrence.
Terrence was right. Boston PD and judiciary was a bastion of homophobia. They’d think the idea of putting three Irish lads in jail for stomping a queer preposterous.
Terrence looked a little faint and started to fall; so I grabbed him. He was pretty beat down.
“Take me home, please,” he whispered
I suggested he go to the ER but he convinced me that wasn’t necessary. He lived in a basement apartment on Commonwealth Avenue. It wasn’t bad and I wondered how he could afford it. Most male hookers live in poverty.
“I just need some rest and I’ll be fine,” said Terrence as I helped him strip to down to a pair of lacy female panties and tumble into bed.
I worried he might be hurt worse than he thought and decided to hang around a while. I helped myself to a beer from the refrigerator and settled down on the couch to watch television and promptly fell asleep.
I woke up to the pleasant sensation of someone sucking my cock. I had a moment where I thought I was back in my parent’s home and Arlene was taking care of me. Her crack of dawn blowjobs are among my fondest childhood memories. But when I opened my eyes, I found myself looking into the bruised face of Terrence.
“Relax, Officer Westbrook, I want to thank you for last night,” said Terrence showing remarkable skill in the art of fellatio. His pink tongue was magic as he worked from my pucker to the tip of my cock head. A long thin finger slipped inside my anus and located my prostate. I moaned my approval of his efforts as the pad of his finger expertly stroked the gland.
“That’s not necessary,” I said but I didn’t move. I admit to bisexuality. My older brother, Winston, used to say that sissies fucked only girls and that it takes a real man to fuck a man. That was his rationale for putting me on all fours and corn holing me when we were kids. Winston wasn’t a hog about it. He let me do the same to him. Gays deny that true bisexuality exists. According to my gay friends, you’re gay, straight, or lying. They’re full of shit. I love to fuck both.
“You take cream in your coffee,” asked Terrence after he swallowed my load with a Las Vegas finish that drained me dry?
“No, black,” I answered feeling a little embarrassed. “How old are you, Terrence?”
“Nineteen,” he said as he hustled off to the kitchen. He was wearing a white satin robe and matching white lace panty. A pair of scuffs completed his ensemble. That was when I noticed the size of the bulge in his crotch.
It was daylight and I knew how nineteen looked. “Really,” I asked?
“Seventeen,” he said.
“Honestly,” I asked again?
“Sixteen but I have a birthday coming up next month and that’s the God’s truth,” said Terrence. “Why don’t you get cleaned up? The green towels are for you.”
“No thanks, I better get going,” I said standing up.
“Why? Do you have to work today?” asked Terrence.
“No, not until six,” I said. I was on evening shift.
“How do you like your eggs?” asked Terrence.
I hesitated a minute. At the time, I was between girl friends. Being a rookie cop is demanding and I didn’t have time or energy to haunt the meat markets and find company. Plus I was curious what was hiding underneath the crotch of those white panties.
I found out after breakfast. It was eleven inches long and five inches in diameter. A cock that size was in demand and produced enough income to afford a decent apartment. Only the head would fit in my mouth but the entire package made its way down my rectum. I’m versatile so my nine inches fit inside Terrence’s hole. We sucked and fucked all afternoon until I had to go home and get ready for work.
After that, Terrence became one of my snitches plus a regular fuck buddy. He passed on useful information on gamblers, pimps, and drug dealers. In return, I made sure he wasn’t arrested or if he was, he was out in an hour. Occasionally, we got together for sex. At times, I helped him out when a John wanted a black and white fucking. Usually, they were married men from the burbs with children and respectable positions in the community. It was something of a hoot for the two of us to pound the living shit out of some overweight middle aged executive leaving him exhausted but so very grateful. We’d send him home to the wife and kids with jism leaking out of his asshole. When I left Vice for Homicide, I lost track of Terri.
“I got married two years ago so I’m Mrs. Lawrence Gilmore now,” said Terri bringing the conversation back to the present.
Massachusetts allowed same sex marriages so it was possible. “Congratulations, where’s Mr. Gilmore?”
“He died three months ago today. Massive heart attack, the doctor said he had a congenital weakness in the left ventricle. He was only forty two. I’m just now getting over it. Larry was the love of my life,” said Terri looking sad.
“I’m terribly sorry to hear that,” I said taking his hand and pressing it. Some of my old feeling for Terri AKA Terrence tumbled back into my mind. The fact he looked so damn hot helped.
“I had five years with him and I treasure every day. He treated me like a goddess. Larry had money and he paid for my surgeries. This building belonged to him along with a couple of others,” said Terri.
“You look terrific,” I said and I meant it.
“Thank you. You look pretty good yourself. I heard about your partner and how you took the fall,” said Terri.
“I was stupid. I don’t know what got into me fucking my best friend’s wife,” I said. “She was one hell of a piece of ass.”
“We’ve both had a run of bad luck. You got to be anywhere soon?” asked Terri.
“Just the autopsy for the victim at three,” I said glancing at my watch. It was almost eleven.
“Stand up and take your clothes off, White Boy,” said Terri stretching her monster out.
I couldn’t feel anything but lust as I stared at his massive cock. I wanted it and would do whatever it took to get it. Terri remembered how I rolled. I’m a submissive bottom when it comes to gay sex, a catcher not a pitcher. I’m six feet two inches of hard cop muscle that wants to be a girl when it comes time for guys to fuck me. Go figure.
Terri also knew how to tap into my white guilt for slavery and other transgressions against his race. I was raised in a liberal home whose parents traced their ancestry back to prominent abolitionists. Somewhere buried in my psyche was the idea that subjugation of the Negro by the white man could only be atoned for by submitting to the black man’s cock. I often wonder what Freud would say to that.
With women I’m dominant. However, I have been known to switch in either case. Male friends say I’ve grown more submissive since the suicide of my partner and that I’m seeking to be punished for what I did. Females say I’ve become more dominant as a means to express my rage for the unfair treatment I’ve received.
My sister Arlene thinks I need therapy. Fuck that. I think therapy is a crock of useless bullshit. I refuse to go even though there is a psychologist on staff and career wise, seeing her would be a good move.
One thing I realized was sex with a gorgeous black transsexual who knew which buttons to push was going to make for one hell of an afternoon.
“Come here, White Boy,” said Terri when I was nude. She wrapped her hand around my cock when I stood in front of her.
“Yes, Ma’am,” I said feeling my manhood grow at her touch. I resisted the urge to throw myself at her feet and beg her to fuck me.
“Have you ever sent your DNA off to one of those labs so they can trace your genealogy?” asked Terri taking a firm grip on my balls with the other hand. She squeezed just hard enough to make me gasp with pain. I’ve got a nice set of low hangers that tops love to twist.
“No, Ma’am,” I managed to say through clinched teeth.
“You should do it sometime because somewhere in the Westbrook line is a black man with a cock like yours. This is a black man’s cock. Are you sure one of your grandmothers didn’t satisfy her craving for nigger dick?” said Terri stroking my shaft and squeezing my balls.
It was a pain and pleasure move that made me want to beg and plead for her to do whatever the hell she wanted with me. But I managed to stay focused. “Not that I’m aware of. We’re Nordic stock.” Both sets of my grandparents arrived in this country from Norway right before the Second World War. Except for my older brother Winston who has red hair and green eyes, we’re all blue eyed blondes. But Terri was right. My cock was a two inches shorter version of his. If you dyed it brown, it was a black man’s cock.
“Come with me, White Boy. I’m going to prettify you before I fuck you. Some of my buddies would love that cute white ass of yours,” said Terri using my penis as a handle to take me into the bathroom.
“Sit on the commode. Lean back and spread your legs,” said Terri after we reached the bathroom.
I watched in awe as Terri shaved my privates then my legs. I’m not that hirsute, but there was golden fuzz covering my manhood. It was a first for me. In a way, it was like she was taking away my masculinity. She was making me like her.
“Turn around, bend over and spread your cheeks, that’s what the guards at the Essex County jail used to say to me before they gave me a finger wave,” said Terri.
The jailors over at Essex County were known throughout the correction system for their cavity searches, especially for women prisoners. There is a chubby matron named Margo who claims her fat fist had been inside more than ten thousand cunts ranging in age from twelve to eighty. I once watched Marge demonstrate her technique via a hidden security camera. The fourteen year old shoplifter just might have been scared straight by the experience of having Marge’s fist force its way inside her pussy and anus, causing severe pain judging by the way she screamed her head off. The coup de main was when Marge’s shit covered hand went into the girl’s mouth the minute it left her asshole. Being left naked on a cold concrete floor in a pool of your own vomit with a bleeding asshole is a powerful deterrent to petty crime.
I eagerly complied with Terri’s request and a moment later, my anus was a hairless as my balls. Bottoms love to expose their anus to tops.
“Now, I’ll clean you out. Can’t have you getting caca on my dick,” said Terri filling a pumpkin shaped enema bag with warm water then adding Castile soap. The soap burned like hell but it left the inside of your bowels sparking clean.
I started to cramp as soon as the water reached my lower intestine. I broke into a sweat and held my abdomen as the cramps worsened. Terri made me wait before she allowed me to take a seat and let fly.
“Do you love me, Simon,” demanded Terri straddling my legs and taking my head in her hands as I released my bowels? His semi erect cock was inches from my mouth; so close I could almost taste it.
“Yes, Terri, I love you,” I said and at that moment I meant it.
“Prove it, Simon. Show Terri how much you love her,” said Terri sticking her cock in my mouth.
I knew what was coming. Obviously, he hadn’t forgotten the kinky things that turned me one. Water sports are high on my list. Urine flooded my mouth and I quickly gulped down the first mouthful then sucked hard on his piss hole for more.
“That’s right, White Boy, swallow that black piss. Drink it down like it was your Mom’s tittie milk.
I was thrilled Terri was allowing me to drain his tank. By the time, he finished, I’d taken in almost as much liquid on one end as I’d shot out the other. I could feel the weight and warmth of all that pee as Terri ushered me into the shower to clean off. He handed me some kind of perfumed soap that made me smell like a girl.
Shaved, douched, and smelling like a French whore I presented myself to Terri in the bedroom.
“Slip this on,” said Terri handing me a garter belt and hose from his extensive collection of large sized lingerie. Since he and I were about the same size, everything fit.
It was a half hour later when Terri looked me over and declared, “Not bad, Simon, you look fuckable. You can be Arlene for the afternoon.”
Terri had one hell of a memory. I’d confided in him about the things I did with my brother and sister. But it had been ten years since he last dressed me in women’s lingerie and called me Arlene while he fucked my ass.
I watched in the mirror as he transformed my masculine looks into something bordering on the feminine. From somewhere I recalled that Terri had gone to cosmetology classes and had actually worked a cosmetics counter at one of the department stores downtown. I was wearing a platinum blonde wig and make-up that matched my complexion. A sexy garter held up my white hose. Matching thong panty barely covered my cock. A pair of white pumps looked right although I wasn’t sure I could walk across the room without falling.
“Let’s see if anyone wants to join us?” said Terri dialing her cell. “Charles, darling, you busy?”
“Fabulous, I’ve got an adorable white shemale here who is desperate for black cock. No, he’s an old friend. He’s also a cop so not a bad dude to know in case your black ass gets arrested again,” said Terri.
“The call ended with, “See you in five.” Terri immediately dialed again. “Reggie, you busy?”
I listened as she invited another of her friends to come and fuck me. Thank God, she quit after she invited someone named Kelso who Terri assured me had a bigger cock than his.
I can’t say I wasn’t eager for what was about to happen. The thought of pulling a train of well hung black guys is every white boy’s dream fuck.
“I got just what we need in the way of stimulation,” said Terri selecting a DVD from a bookshelf. “White Shemale Gangbang No. 5, its high definition,” read Terri holding up the case.
“I’m not a shemale. I don’t have boobs, Ma’am,” I said.
“I know a board certified plastic surgeon who’ll make you a pair. He did mine,” said Terri inserting the DVD in the player.
I stood staring in the mirror contemplating what I would look like with breasts. I’d worked vice for a year. That brought me in contact with the world of transvestites and transsexuals, even the rare transgendered. On several occasions, I’d dipped into man made pussy. It wasn’t bad and the thought that my cock was inside a penis that had been hollowed out and reversed into the body cavity was enough to get me off. However, the faux clit that was carved out of the penis head didn’t quite look right although you could suck it like a regular clit.
My reverie was interrupted by the door bell. Seconds later, Charles appeared and I recognized him. Charles Darnell played wide receiver for Boston College Eagles, my alma mater. I’d watched him terrorize defensive backs for the last two seasons. He had broken every wide receiver record BC had. NFL teams were salivating over him signing up for the draft. At six four with an incredible athletic physique, he was Arlene’s wet dream.
“Charles, this is Arlene,” said Terri.
“Come here, Arlene,” said Charles pulling me into his arms for a kiss. One hand reached down and grabbed my buttock pulling me hard against him. The other grabbed my nipple and worked it in his powerful hands that could snatch a ball out of an opponent’s grasp.
We broke the kiss for a moment so Charles could take off his sweats. He was magnificently equipped and it thrilled me down to my toes to take his warm cock in my hand.
“Arlene’s a pig slut,” said Terri informing Charles of how to use me. Those three letters, “pig,” said it all. The first time I heard them was when Winston called me his pig brother then pissed in my mouth.
“My kind of whore,” said Charles taking me back into his arms for another kiss. “Open your mouth, Arlene.”
I held my mouth open as Charles let a king sized gob of spit cascade over his bottom lip onto my tongue. I savor the slimy fluid then swallowed it. Charles raised one arm toward the ceiling presenting me his armpit. The fingers of his other hand captured my nipple. I knew the pig drill. I placed my tongue at the base of the pit and licked upward. My tongue retraced its path leaving a streak of saliva.
I whimpered as he applied pressure to my nipple. His fingers were like iron. Once he had his hands on a football or a male mammary, nothing was going to make him let go. I buried my face in the pit, working my tongue over the wrinkled flesh. Fastidious types are repulsed by the aroma produced by the male sweat glands but not yours truly. I consider it one hell of a turn on.
I was whimpering in pain as we kissed. Both of my nipples were being crushed as he practically lifted me on the ground using them for leverage. After I’d whimpered enough, he pushed me to my knees and I began sucking his cock. Terri got in on the action and I was switching my mouth between dicks. Of course, the race card was always available to play.
“Arlene loves black cocks. He can’t get enough of them. Right Arlene?” said Terri.
“I love black cocks. They’re so beautiful and they’re so big,” I said as I ran my tongue over the ebony surface. They felt so warm and vibrant on my tongue.
I’m not sure why the white man and this white man in particular find it such a rush to kneel before a black man and make love to his manhood with his mouth. I’ve sucked my share of white cock and while it can be great too; there just not the same intensity of feeling. The bottom line is I adore sucking a big black dick. Who doesn’t?
“Arlene wants to drink my piss. Don’t you, Baby?” said Charles.
“Yes, please,” I said.
“He’s already emptied my tank,” said Terri.
I managed to swallow everything he gave me without spilling a drop.
“Where’s you get this white boy, Terri” asked Charles suitably impressed with my performance.
My view is that the sexual humiliation of the white man by the black increases the pleasure of both races. The black man enjoys the sense of payback as he repeatedly fills the white man’s mouth with his urine. The white man believes he is atoning for past wrongs. I’m no psychologist but that is how I understand it.
“You fuck him while he eats my ass,” said Charles lying back on the bed and raising his legs to give me a clear shot at his sphincter.
A minute later, I’m taking Terri up the butt while trying to work my tongue past Charles’ sphincter. We were going hot and heavy when Reggie and Kelso showed up. Kelso promptly replaced Terri as my ass fucker.
Kelso’s cock wasn’t long but it certainly was thick. He also brought along a can of Crisco vegetable shortening which meant I was going to be fisted at some point.
Terri announced that since Charlie, Reggie, and Kelso were tops, he was going to bottom with me. It was cute the way he wiggled his ass, inviting Reggie to stick his pecker inside.
One of the best parts of the afternoon was lying on my back beside Terri holding hands and kissing while the others fucked us. It was intense especially when the tops took their cock out of Terri’s ass and stuck it in my mouth or vive versa.
“Just like the old days,” remarked Terri.
Toward the end, Kelso packed our rectums with Crisco. It’s a very intense feeling to have a man’s hand and forearm up your bowels. Charles obliged me by sticking his fist in my ass and sucking me off.
“That’s quite a big load for a white motherfucker,” said Charlie after he gulped it down.
The finale came when they put Terri and me ear to ear and gave us a facial. Terri and I kissed as we licked sperm off each other’s face.
As I was driving back to headquarters, the thought occurred to me that the Cynthia Rose case was not going badly. Terri had promised to get me in touch with someone who could wrangle an invitation to a Club Macabre event.
Hooking up with my old friend Terri boosted my morale. He’d offered to teach me to dress as a woman something I had always wanted to do. Terri believed that with a little coaching I could pass. He’d also mentioned the possibility of our going in drag to Chez Jacques for dinner and dancing. Just the thought of being on the dance floor in a man’s arms gave me a hard on.
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