City of Angels

I rushed over to pick Lisa up, concerned we might be late for our flight to L.A.. It didn't help that Lisa had 2 suitcases, but I know she never travels light. She always takes too much and insists on checking luggage. I quickly grabbed the bags and raced to the airport, happy to get away on my birthday for early November weekend getaway with Lisa. It felt good to get on the plane and look forward to a fun time with my friends-with-benefits partner.

A little background on Lisa. I met her online when I was rebounding from a divorce. She was the perfect antidote for 34-year-old guy bound up in dull marriage for 12 years. She was 5'-6", a perky, brunette who was 5 years younger than me. We didn't have a lot in common. She was kind of spacy and a party girl and definitely not the kind of girl you'd take home to mom. But she sure caught my eye because she was good looking and had the nicest pair of tits I have ever had the pleasure to enjoy.

She also made up for a lackluster sex life in previous marriage. She was formerly the wife of a preacher and in an amazing twist to my way of thinking, she was downright wild and a bit kinky in her outlook on sex. On our first phone call, for instance, she let it out that she had a whole trunk full of sex toys. As you can imagine it didn't take long for us to consummate this relationship.

Anything was fair game with Lisa. One of our favorite past times was meeting up at a bar so she could show off her sensuous body. It was a thrill for her and me and usually for the other guys she entertained at the bar. I could go on and on but suffice it to say she was a fantasy come true.

Our indulgences took on another flavor once on a getaway road trip. As it turns out we went to romantic B&B in southern California for my birthday. Even though it rained all weekend, it was a weekend to remember. After we had breakfast delivered to our room, she brought out four bags and boxes and laid them out on the bed. She looked at me with anticipation and said, "Now, knowing your birthday was coming up, I have been planning this trip for a while ... And I want you to really be open minded for what I have in store for you." This little prelude had me intrigued; I mean we've had some wild times that always led to great sex, and this sounded very promising.

She beckoned me to open the first package. I grabbed a box and tore open the wrapping and was surprised to see it contained black, lacy lingerie. As I lifted it out, I held up a sexy corset with garters and a matching black panty and several pairs of nylons. I smiled, imaging what this might look like on Lisa and said, "Well this could make for a fun weekend." She smiled and said, "Yeah, I think we can put this little ensemble to good use. Now keep going," and she gestured to the other gifts. I next opened a box containing a very sexy pair of black high heel sandals, with 4-inch heels and sexy little straps that fastened in front. "Nice," I commented, seeing a theme emerge from the gifts. Lisa then placed the last 2 gifts in front of me and said, "These complete the ensemble." I reached into a bag with lots of tissue paper and removed the next gift, which turned out to be a blonde wig. Okay, that's odd, I thought. I looked at Lisa questioningly and she merely pointed to the last gift box. I hesitantly opened the box and it contained a pair of silicone breast forms.

OK, not exactly the type of birthday presents I expected. Then again, maybe not a big surprise knowing Lisa. I flashed back to a time about a month ago when she had coaxed me into wearing her underwear while we were in bed together. I played along with her little fetish at the time because we had just started dating and sex with her was wild. I remember falling asleep in her undies while she spooned me. She also confided to me that she occasionally got her former husband, the minister, to dress up in women's clothes for her.

I stammered, "Uh, Lisa ... what's going on here?" Lisa cleared her throat, "Well I thought this trip away might be a good time for us, er you, to take a walk on the wild side. I've been thinking about this since the night you dressed in my bra and panties ... that was fun for me, and I thought you enjoyed it too. That's one reason I wanted to go on this trip with you." Still dazed by this turn of events, I said, "Well I enjoyed it because we were having sex." Lisa smiled at this, saying, "Oh Dennis, if you do this for me it's going to turn me on, and you better believe I'll be all over you. I want to dress and doll you up, like I used to do with my ex." I scoffed and said something like no way Lisa, but she got that sexy look and said, "Just indulge me. You'll see, this will be fun. I want to make you my plaything. Hey what else do we have to do all day?" and we both looked outside at the wet, dreary weather.

I took in Lisa's expectant face and the gender bending assortment of gifts displayed in front of me. She had obviously planned this for some time and spent a lot of money on the presents. I'm not going to say this was a no-win situation, because part of me was fascinated by the idea of Lisa dressing me up as her female plaything. But in truth, she had backed me into a corner, and I really couldn't say no since it could ruin our weekend and maybe end the relationship. With as much seriousness as I could muster, given this rather bizarre situation, I said, "Okay I'll go along with this, but you gotta promise, this stays between you and me. You cannot ever tell a sole." Lisa squealed with delight and grabbed me in a hug, saying, "Yeah, just you and me babe!" and winked.

Now it was becoming clear why this sexpot was going out with me. Afterall, I am only 5'-8" and weigh 154 pounds and definitely not anything like the studs she talked about dating before me. Seems that Lisa was only dating me for the very purpose of making me into her, what did she call it ... sexy feminine plaything. I wasn't even sure how to take this; yeah, the sex was great but this was getting weird. Oh well, I thought ... why not. I sighed and said "Okay, I'm all yours."

Lisa promptly stood up, clapped, and told me to strip, adding, "Just relax and enjoy this, and think of it as getting in touch with your feminine side." With all the time in world, we first jumped into the oversized bathtub together that she filled with a flowery bubble bath. While I played with her breasts, she took out a razor and said, "You better knock that off buster or I might nick you somewhere important," as she proceeded to shave me from head to toe. I didn't mind the legs, because I am a swimmer and didn't think this would be hard to explain. I did protest, however, when she shaved my chest, my crotch, and underarms, but Lisa was on a mission and not to be denied.

Out of the bath, Lisa dried me off, put some wonderful powder over my body and led me into the bedroom where she had me lay back on the bed. "First things first my little honey," she said as she grabbed the pair of breast forms and positioned them over my chest, "We need to change your anatomy up here." She used the adhesive that was provided to attach the breast forms to my smooth chest. She told me to hold the forms in place while the adhesive dried, so I cupped my new fake boobs. They were a big handful of breasts and were soft and squishy as I held them. I was fascinated by them because they looked so real and the pert nipples made it look like I was a woman aroused. Lisa brought out some make up to conceal the seams at the outer edges where the forms attached to my skin. After five minutes or so I stood up and immediately noticed the odd sensation of a weight pulling down from my chest. I looked down and saw very realistic looking breasts with pert nipples. Amazing! They looked real and jiggled when I moved. "They are a full C-cup size, which are about right for your body frame," she informed me and added with a laugh, "Plus, there's no way I would allow you to have bigger boobs than me."

Next, Lisa opened the package holding the lingerie and handed me the corset and nylons. Rolling up the nylons she said, "Girls don't wear nylons much anymore, but I know how much you love me in stockings, so I wanted you to experience how sexy they make you feel." Lisa placed the stockings on my feet and showed me how to pull the nylons up my legs. The nylons almost came up to my crotch and had a lacey top to them that looked very feminine. Lisa explained, "These are sized for a taller woman than you, so I am hoping they won't show if you wear a short skirt." The nude nylons gave my pale legs a sun-tanned look. Perfect for California.

I have to admit that this felt very sensuous. She next placed the corset around my mid-section and begin fastening from the back. Once fastened. she pulled on some laces I didn't realize were there and I gasped for air while she cinched the corset around my waist. She laughed and said, "Hey suck it up sweetie ...maybe now you'll have more appreciation for what women go through to look good for men." With my waist drawn in a couple inches she then instructed me on how to fasten the garters to the stocking tops, saying, "These stockings will hold up on their own, but I think garters are sexy and complete the look."

She handed me the matching panties and asked to put it on. There was no way that would work for me, however, because putting on the lingerie had caused me to get hard. Lisa smirked and said, "It looks like somebody's enjoying themself." For reasons that may have to do with having shaved legs or simply giving in to the experience, I was excited. Somewhat embarrassed, I didn't want to admit that I felt out-of-my-skin sexy. Instead, I told Lisa, "Hey, you're dressing me in this sexy lingerie and I got turned on a bit by the silky feel of the stockings on my shaven legs." Lisa gave me that I told you so look and then laughed when she cinched me in even tighter to the corset.

When done she looked at me and said, "Sweetie, this will never do," and she went down on her knees and used her exquisite mouth to take in my cock. While stroking my nylon-clad leg she vigorously licked and sucked on me until I came, surprisingly fast. When she has swallowed the last of my load, she said with mock seriousness, "We cannot have your woodie sticking out like that again; it's time to put this bad boy away."

Lisa told me to step into the black lacy panties and pull it up. She deftly took my now deflated penis and scrotum and pushed them back between my legs. Lisa then explained that I could push my balls into some inner recess and showed me how it was done. She added," These panties have a special pocket between the legs to hide your penis," and Lis quickly tucked my flaccid manhood back between my legs. I didn't ask Lisa how she knew to do this but could only marvel that the front of my pelvis encased in the black panty was flat, and even a little rounded, like a woman's. The panties were a marvel, snug and elastic to cover me entirely yet all embroidered lace in a high cut on my hips. I looked in the mirror and saw the delicate, lacy panties covered my front and rear end in a V-shape that was totally sexy.

Next, Lisa made me sit and got the high heels out and slipped them on my feet. She said,

"These are a size 10, which is only 1 size larger than what I wear." I was amazed that they fit well and realized Lisa must have gone to some trouble to figure out the right size. These spikey heels on the shoes looked so dainty I had to let Lisa know, "They're sexy ... but there's no way I can walk in these." Lisa laughed at me again, she was doing a lot of that, and said, "Don't worry honey, you'll get used to it."

I realized how much Lisa was enjoying this and, truthfully, so was I. Also, it wasn't lost on me that Lisa was calling me honey, sweetie, and babe. In my suspended reality state, I kind of liked it and felt like I would do anything for her. Lisa had me stand and with some effort I was able to get up and take a few wobbly steps in the heels. Not exactly the picture of grace and femininity but as I adjusted to the strange feeling of perching more on my toes, I was astonished that the heels were remarkably comfortable. "Don't worry babe, we'll practice later," she said and steered me to the bathroom saying, "We're far from done here."

Lisa sat me in front of a mirror and said, "Now it's time to do your makeup," as if that was the most natural thing in the world she could say to her boyfriend. With me in a daze, Lisa arranged her make up on the counter and proceeded to carefully apply concealer and makeup while highlighting my cheek bones with some blush. Next, she took one of her many brushes and coloring tools and shaped my eyebrows. Asking me to hold very still, she then used eye liner to create a dark line above my eyelashes and then brushed a smoky grey eye makeup with some lighter highlights toward the outer eyes. From out of nowhere she produced a set of false eyelashes and glued them on to my own rather meager eyelashes and generously applied mascara to my upper and lower lids. After what seemed like ages, she brought out a red pencil and drew a deep red outline around my lips. Satisfied with her work, Lisa then took out a glossy and bright red tube of lipstick and carefully covered my lips. That felt so sensuous.

After asking me to smack my lips together she frowned and playfully slapped me on the cheek, saying "It's not fair. You have a perfect face, beautiful brown eyes, high cheek bones and such luscious and full lips," adding, "Any girl would die to have your features. I'm totally jealous. And hey, I don't want to insult your manhood, but let me tell you sweetie that you have a more feminine than masculine look and the makeup really brings it out. Wow, your eyes, your lips ... I mean, you're much more beautiful made up as a woman."

Now this whole thing had my head spinning. Lisa was right; I was transforming into a woman right in front of my eyes. And it felt good too; all the pampering and primping. Lisa wasn't through yet. She got the blond wig and placing her hands inside the wig, she slipped it over my head. The wig had a soft feminine cut with loads of layers that fell to my mid back. "Now this," she said, "Is very expensive and looks as real as they come." She looked over the result and tugged the wig this way and that and pinned it to my hair on both sides. Lisa took out a brush and combed and teased the long blond locks into a wavy frame around my face. At last, she seemed pleased with her real-life Barbie doll experiment. Then, as if talking to herself, said, "We'll have to pierce you ears so you can wear my earrings."

"Okay, now let's look at what we've got," Lisa said as she motioned for me to stand up and move in front of the full-length mirror at the other side of our bedroom suite. This snapped me out of my trance, and I slowly got up, carefully walked in very small steps across the room and turned around. I don't think I have ever been so self-conscious in all my life. This had gone too far ... here I was standing in front of my girlfriend in sexy lingerie, nylons and heels, long blonde hair and bright red lips, and with what even I would admit was a fine set of boobs spilling out of the top. Lisa, realizing I was overwhelmed, came over and hugged me. What a strange sensation to feel my breasts pressed against hers and seeing my long blonde hair falling over her shoulders as we hugged. She pulled me away at arm's length and she softly said, "I could have never imagined you could look so hot as a chick". Lisa was right, looking back at me was a stunning and sexy lady ... tall and curvy in all the right places. I waved my hand just to make sure that was me in the reflection.

"Well, well, I must say my little project turned out better that I would have ever thought," Lisa said while also gazing in the mirror. "You just ooze sexuality." And with that, while we were both still staring at the mirror, she began caressing my breasts and placed her arm around my waist. I looked at her and she leaned in and kissed me. It was a totally different experience. She lightly touched my lips and I softly and delicately responded, with a trace of tongue licking her lips as I pulled away. Stroking my long blond hair, Lisa said, "I think I could get into this lesbian thing with you and slapped me on my ass." Consciously or not, I realized that I was taking on a different persona .... I liked Lisa taking control. It was as if I wanted to be my most feminine self.

Lisa broke the spell saying, "my idea was to doll you up, play with you and have you lick me to orgasm with that beautiful red mouth of yours. ... But now I am so enthralled with you, with what you've become, that I want to take you out on the town and show off my pretty girl." That sure brought me back to reality. I pulled away from Lisa and said "No, absolutely not. Are you crazy? I let this thing go too far already. This has been kind of fun in our little hotel room but there's no way I could leave here. I could never pass as a girl."

Lisa laughed and said, "Sweetie, that mirror doesn't lie. You look sensational, a real hottie. Believe me, no one will know. I think your real problem will be fending off the guys hitting on you." Lisa then got serious, "Hey I told you I did this sometimes with my ex but I got to tell you that it was just a game for us. He never really looked very convincing as a woman. But you, on the other hand, look like a Victoria Secrets model. You look so good that I want to take my creation out in public. It will be a wild ... we'll can both have fun with it. Me, to enjoy how everyone, especially men, react to you, and you to see what it's like being a sex object." Still sensing that she had pushed me too far, Lisa added, "Look, babe, let's just order up a bottle of wine, get dressed to go out, and if it still doesn't feel right, I'll let it go." Without giving me time to respond, Lisa picked up the phone and ordered a bottle of chilled rose.

We both donned bath robes and Lisa went to her suitcase and began laying out some clothes on the bed. "I didn't get you a dress for your birthday, but I expect any of my outfits will fit since you're not that much bigger than me." With that she held up several dresses and asked me what I thought. Before I could answer, we were interrupted by a knock on the door. Lisa opened the door to our suite, invited the young man holding a bucket of ice and wine bottle into our suite and told him to put the wine on the table by our sitting area.

Reading his employee badge, Lisa said, "Hi Josh" and without missing a beat, Lisa looked at me and said, "Susie, why don't you grab some bills from my purse and give this nice man a tip?" I nearly froze and didn't move until Lisa gave me a hard look. I had to walk to the other side of our bed to reach her purse and my hand was shaking while I fished out a $5 bill. Lisa, in the meantime, was asking Josh where we might find a nice restaurant. Trying to regain my composure, I straightened up and walked to where Josh was standing to hand him his tip. As I approached, though, my heel caught on the carpet, and I lost balance. Fortunately, Josh grabbed me before I fell and pulled me upright. I was so flustered that I quickly pushed the tip into his hand and tried to pull away. It was then that I realized that in pitching forward, my robe came open, down to the sash, and Josh had a full and closeup view of my corseted front. I looked down and realized that my new, and I have to admit, life-like breast forms encased in the lacy cups of the corset were prominently displayed. We both froze and Josh's eyes were like saucers as he took in this unexpected show.

Lisa swooped in to rescue me, saying, "My girlfriend is such a klutz." Josh released me and abruptly turned and barged out the room. As the door closed, Lisa broke out laughing, saying, "You gave that poor guy a view that will stay with him a long time. If I didn't know better, I'd think you planned that to give him a thrill. I bet he'll go home tonight and jack off with the picture of sexy blond displayed in front of him with her tits spilling out of her bra." Not ready to see the humor in this, I bee-lined to the wine, opened it and poured a tall glass, and collapsed into the nearby couch.